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  • 1990-1994  (4,880)
  • 1970-1974  (3,840)
  • 1890-1899  (2,182)
  • Organic Chemistry  (10,127)
  • Electron microscopy
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Material
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Year
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  • 1
    Electronic Resource
    Electronic Resource
    Widespread aluminium deposition in extracerebral organ systems of patients with dialysis-associated encephalopathy (1994)
    Springer
    Virchows Archiv 424 (1994), S. 105-112 
    Details
    ISSN: 1432-2307
    Keywords: Silver staining ; Aluminium ; Laser microprobe ; Electron microscopy ; Dialysis-associated encephalopathy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract We have described new silver-staining methods for the demonstration of lesions in senile dementia of the Alzheimer type. The same procedure was used to visualize characteristic aluminium (Al)-containing inclusions in choroid epithelium, glia and neurons of the central nervous system in dialysis-associated encephalopathy (DAE). Here we describe the patterns and degree of Al deposition in extracerebral tissues of 12 DAE autopsy cases. Light microscopy of silver-stained paraffin sections demonstrated autonomic ganglion cells filled with numerous intracytoplasmic black-stained fine granular inclusions, which were also seen in endocrine tissues (pituitary, parathyroid and adrenal) and in Leydig cells. Heart, liver cells and the testicular tubules were involved, but decalcified bones, haematopoetic elements, hyperplastic epithelium and one case of malignant epithelium lacked inclusions. Laser microprobe mass analysis revealed prominent Al-related mass signals within the en-bloc silver-stained inclusions which were seen at low intensity in adjacent non-stained structures. Electron microscopy demonstrated accumulations of small electron-dense granules intermingling with lipopigments.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00197400
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  • 2
    Electronic Resource
    Electronic Resource
    Sarcoma of the pulmonary artery: report of four cases with electron microscopic and immunohistochemical examinations, and review of the literature (1994)
    Springer
    Virchows Archiv 424 (1994), S. 217-224 
    Details
    ISSN: 1432-2307
    Keywords: Pulmonary artery ; Neoplasm ; Sarcoma ; Immunohistochemistry ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Herein we report the clinicopathological features of four cases of pulmonary artery sarcoma that appeared at our institution during a period of 30 years. The patients, 2 males and 2 females, were 50–62 years old. Tumour was found in the pulmonary trunk and right pulmonary artery in all cases, in the pulmonary valve and left pulmonary artery in three of the four cases, and in the right ventricular outflow tract in one case. There was direct extension or metastases to the lungs in two cases, the heart in one case, mediastinum or lymph nodes in two cases and the pleura in one case. Ultrastructural examination in one case revealed cells with features of smooth muscle cells and myofibroblasts. Immunohistochemical examination of three cases gave the following results: vimentin and smooth muscle specific actin was positive in all three cases, desmin in one case and cytokeratin in one case. No positivity was found for Factor VIII. This and other studies indicate that histologically most pulmonary artery sarcomas are leiomyosarcomas or “undifferentiated spindle cell sarcomas”. Immunohistochemical and ultrastructural examinations favour an origin from myofibroblasts, probably derived from multipotent (undifferentiated) cells in the wall of the vessel. Most lesions show extensive intrathoracic growth although they rarely metastasize outside the thoracic cavity. They have a poor prognosis although some cases are currently being diagnosed during life.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00193503
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  • 3
    Electronic Resource
    Electronic Resource
    Ultrastructural localization of tissue factor on monocyte-derived macrophages and macrophage foam cells associated with atherosclerotic lesions (1994)
    Springer
    Virchows Archiv 425 (1994), S. 49-54 
    Details
    ISSN: 1432-2307
    Keywords: Thromboplastin ; Atherosclerosis ; Electron microscopy ; Cell culture
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The expression of tissue factor (TF) antigen by circulating monocytes, cultured macrophages, and macrophages associated with atherosclerotic lesions was ultrastructurally analysed using immunogold labeling. A subpopulation of macrophages associated with the intimal surface overlying lesions had a significant TF expression. Macrophages and macrophage foam cells that projected from the intima into the arterial lumen also expressed a high level of TF (14-fold increase over control). In contrast, circulating monocytes and macrophages in culture did not express TF above background control levels. This TF expression by macrophages in vivo but not by macrophages cultured from either normal or hypercholesterolemic animals suggests that monocyte activation and macrophage transition, as measured by TF expression, is lesion-dependent and not stimulated solely by intimal attachment, surface migration, or hypercholesterolemia. These results further suggest that macrophages and foam cells associated with early lesions of atherosclerosis can initiate fibrin formation, which could contribute to lesion complications and transition to a fibromuscular stage.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00193948
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  • 4
    Electronic Resource
    Electronic Resource
    Uptake and phototoxic effects of aluminum-chlorophthalocyanine (AISPc) in hurnan bladder carcinoma cells (1994)
    Springer
    Urological research 22 (1994), S. 79-83 
    Details
    ISSN: 1434-0879
    Keywords: Phototoxicity ; Aluminum-chlorophtalocyanine ; Electron microscopy ; DAB staining
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract In vitro experiments were performed on human bladder carcinoma cells to evaluate the uptake of aluminum-chlorophthalocyanine (AlSPc) and the subcellular target of phototoxicity. In order to quantify the correlation of intracellular uptake and incubation time and to identify the primary subcellular target of phototoxicity, fluorescence and absorption measurements have been carried out as well as electron microscopic studies. Absorption and fluorescence measurements showed the largest value after 24 h of incubation time. Fluorescence microscopic studies suggested the sensitizer to be located in a brighter patch within cytoplasm. Electron microscopic studies using DAB (3,3′ diaminobenzidine) staining showed that the mitochondria are the primary target of phototoxic activity of AlSPc and that the majority of vacuoles of treated cells were originally mitochondria.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00310996
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  • 5
    Electronic Resource
    Electronic Resource
    Madin-Darby canine kidney cells are injured by exposure to oxalate and to calcium oxalate crystals (1994)
    Springer
    Urological research 22 (1994), S. 197-203 
    Details
    ISSN: 1434-0879
    Keywords: MDCK ; Calcium oxalate ; Oxalate ; Scanning ; Electron microscopy ; Trypan blue ; Adenine
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The reaction of Madin-Darby canine kidney cells (MDCK) to potassium oxalate (KOx), calcium oxalate monohydrate (COM) crystals, or a combination of the two was studied. The most noticeable effect of exposure of the cells to either KOx or COM crystals was loss of cells from the monolayer ranging from 20% to 30%, depending upon the particular treatment. Cellular enzyme values in the media were elevated significantly by 12h of exposure, although in specific instances, elevated levels occurred at earlier time periods. As regards the monolayer, trypan blue exclusion was decreased significantly, although amounting to only a 4–5% reduction. Specific tritiated release occurred at 4 and 12 h after exposure to KOx and at 12 h after exposure to crystals. Structurally, COM-cell interactions were complex and extensive endocytosis was noted. Cells were released from culture either as cellcrystal complexes or from the intercellular spaces after exocytosis. When treatment were combined the effects were only slightly additive, but the two treatments potentiated each other: all media enzyme levels (with one exception) were elevated at 2 h, tritiated adenine release was present at 4 h, and there was more extensive cell loss from the culture monolayer. These data suggest that both KOx and COM crystals damage MDCK cells when applied alone, and in concert they act synergistically.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00541892
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  • 6
    Electronic Resource
    Electronic Resource
    Neuronal vacuole formation in the rat posterior cingulate/retrosplenial cortex after treatment with the N-methyl-d-aspartate (NMDA) antagonist MK-801 (dizocilpine maleate) (1994)
    Springer
    Acta neuropathologica 88 (1994), S. 511-519 
    Details
    ISSN: 1432-0533
    Keywords: Vacuolization ; Neurotoxicity ; Neuropathology ; Electron microscopy ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Cytoplasmic vacuoles appear in neurons of the posterior cingulate/retrosplenial cortex (PC/RS) of rats after treatment with N-methyl-d-aspartate (NMDA) receptor antagonists. Prominent dilatation of mitochondria and endoplasmic reticulum has been described within 2 h; however, the ultrastructural features of vacuole formation are unknown. To investigate this, the present study examined the PC/RS cortex of male rats (age 60–70 days) at 15, 30, 45, 60, 90, and 120 min after subcutaneous treatment with 1 mg/kg of the noncompetitive NMDA antagonist MK-801 (dizocilpine maleate, 5-methyl-10, 11-dihydro-5H-dibenzo [a,d] cyclohepten-5,10-imine). Subtle mitochondrial dilatation was identified in a few neurons as early as 15 min postdose (MPD). By 30 MPD, dilatation was more pronounced in mitochondria and also involved the endoplasmic reticulum and perinuclear space. Ribosomal disaggregation and degranulation were also evident by 30 MPD. At all subsequent time points, dilatation of mitochondria and endoplasmic reticulum progressed in severity. Although the relative involvement of mitochondria and endoplasmic reticulum varied, glia were not involved. These ultrastructural data suggest that after treatment with MK-801, mitochondrial dilatation precedes involvement of endoplasmic reticulum in vacuolization of susceptible PC/RS cortical neurons. The early mitochondrial effects identified in this study suggest an initial metabolic insult that rapidly progresses to affect endoplasmic reticulum and ribosomes. This strengthens the relationship between the ability of certain NMDA antagonists to induce energy perturbations and neuronal vacuoles in the same region of the rat cerebral cortex.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00296487
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  • 7
    Electronic Resource
    Electronic Resource
    Cytoplasmic inclusions of astrocytic elements of glial tumors: special reference to round granulated body and eosinophilic hyaline droplets (1994)
    Springer
    Acta neuropathologica 88 (1994), S. 501-510 
    Details
    ISSN: 1432-0533
    Keywords: Key words Round granulated body ; Eosinophilic ; hyaline droplets ; Astrocytic tumors ; Immunohistochemistry ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Round granulated body (RGB) and eosinophilic hyaline droplets (EHDs) have been described as cytoplasmic inclusions of certain astrocytic tumors. In the previous literature, however, these inclusions have been described using various terms or regarded as nosologically the same entity. Light microscopically, RGB appeared as a round discrete body filled with fine uniform granules, while EHDs demonstrated a cluster of bright eosinophilic, round objects of various size. They could be clearly distinguished even by conventional histochemical staining such as the Masson trichrome stain and the phosphotungstic acid hematoxylin preparation. Both RGB and EHDs expressed positive immunoreactions for glial fibrillary acidic protein, several lysosomal markers, and some stress-response proteins. The ultrastructural appearances of these inclusions were distinct, however, one common feature was that they consisted of aggregations of numerous membrane-bound electron-dense bodies. Thus, both inclusions appear to be produced by neoplastic astrocytes and are possibly related to the lysosomal system. We examined the presence of RGB and EHDs in 138 astrocytic tumors. Both inclusions occurred most frequently in pleomorphic xanthoastrocytomas, followed by gangliogliomas and pilocytic astrocytomas. Subependymal giant cell astrocytomas exhibited only RGBs. RGBs and EHDs were not seen in any abundance in glioblastomas, gliosarcomas, fibrillary astrocytomas, protoplasmic astrocytomas, or oligo-astrocytomas. Some glioblastomas, however, showed only EHDs in small numbers. Several anaplastic astrocytomas were associated with a large number of RGBs and/or EHDs, and they revealed only rare mitosis despite marked cellular pleomorphism. Although RGB and EHDs have different morphological features, the presence of these inclusions in abundance may represent either a degenerative change, a long-standing lesion, or an indolent growth of the astrocytic tumors.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00296486
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  • 8
    Electronic Resource
    Electronic Resource
    Neomyogenesis in neonatally de-efferented and postnatally denervated rat muscle spindles (1994)
    Springer
    Acta neuropathologica 89 (1994), S. 85-95 
    Details
    ISSN: 1432-0533
    Keywords: Key words     Neonatal de-efferentation ; Sensory denervation ; Electron microscopy ; Intrafusal muscle fibre types ; Postnatal myogenesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract      The ultrastructure of muscle spindles de-efferented by the extirpation of the lumbosacral spinal cord at the age of 2 days and subsequently deprived of their sensory innervation by the section of the sciatic nerve at 3–4 weeks of age was studied in serial sections of 2-month-old rat hindlimb muscles. De-efferentation leaves the primary sensory neurons and their peripheral axons intact and capable of inducing the muscle spindle morphogenesis during the critical period of their development. In de-efferented and subsequently denervated muscle spindles, new supernumerary intrafusal muscle profiles (SIPs) appeared in the muscle spindle A region. They were formed in intimate spatial relation with the original intrafusal muscle fibres (IMFs) predominantly from activated satellite cells derived from both nuclear bag (larger diameter) and nuclear chain fibres. SIPs, however, lacked the typical nuclear accumulations, as well as other ultrastructural distinctions present in control IMFs. The majority of differentiated SIPs separated from original IMFs, whereas the less differentiated SIPs were usually closely apposed to the surface of the parent IMFs and both were covered by the common basal lamina. In some spindles, the original IMFs and/or new SIPs at different stages of their differentiation were found together and they formed clusters of variable shape and composition. In the majority of clusters, all profiles seemed to be isolated along their entire length, although in few clusters, occasional cytoplasmic connections of variable length between intrafusal profiles were found. This result is important for the interpretation of the forthcoming study of expression of muscle spindle-specific myosin heavy chain isoforms in denervated SIPs in rat muscle spindles gradually deprived of their motor and sensory innervation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004010050219
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  • 9
    Electronic Resource
    Electronic Resource
    Ontogeny of the endocrine cells of the stomach of sea bass (Dicentrarchus labrax L.): an ultrastructural study (1994)
    Springer
    Anatomy and embryology 190 (1994), S. 507-514 
    Details
    ISSN: 1432-0568
    Keywords: Endocrine cells ; Gut ; Ontogeny ; Electron microscopy ; Dicentrarchus labrax (Teleostei)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The endocrine cells present in the developing stomach of sea bass larvae have been characterized ultrastructurally. Only one endocrine cell type (type I) was found in the presumptive stomach of 9- and 12-day-old larvae, one (type II) and five (types III, IV, V, VI and VII) in the aglandular stomach of 32-, and of 39- to 46-day-old larvae, respectively, and five (types III, VIII, IX, X and XI) in the differentiated stomach of 55- and 60-day-old larvae. A maturation process was established for some of these cells. Types I, II and III and types IV and X were thought to be different maturational stages of the same endocrine cell type.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00235499
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  • 10
    Electronic Resource
    Electronic Resource
    Ontogeny of the endocrine cells of the intestine and rectum of sea bass (Dicentrarchus labrax L.): an ultrastructural study (1994)
    Springer
    Anatomy and embryology 190 (1994), S. 529-539 
    Details
    ISSN: 1432-0568
    Keywords: Endocrine cells ; Gut ; Ontogeny ; Electron microscopy ; Dicentrarchus labrax (Teleostei)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Several endocrine cell types were ultrastructurally characterized during the differentiation of the intestine and rectum of sea bass (Dicentrarchus labrax L.) larvae. Only one cell type (type I) was found in the posterior region of the undifferentiated gut of 5-day-old larvae (phase I). Types V and VI were found in both the intestine and rectum, types II, III and IV in the intestine, and types VII and VIII in the rectum of 9- and 12-day-old larvae (phase II), the rectum alone showing signs of functional differentiation. In phase III larvae, in which both the intestine and rectum were differentiated, types IX, X, XI, XII, XIII, XIV and XV were found in the intestine, only types X, XI and XII being seen in the rectum. Besides these, a new cell type, XVI, was observed in the intestine of 55- and 60-day-old larvae (phase IV), in which the digestive tract was completely differentiated. The endocrine cells appearing in phases I and II showed very scarce secretory granules and the ultrastructural features of undifferentiated cells. Some endocrine cell types in the earliest developmental stages were related to some of those found later. A maturational process of the endocrine cell types paralleled the differentiation of the intestine and rectum, with an apparent increase in the number of secretory granules accompanying organelle development.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00190103
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  • 11
    Electronic Resource
    Electronic Resource
    Immunocytochemical and ultrastructural studies of the motor cortex in amyotrophic lateral sclerosis (1994)
    Springer
    Acta neuropathologica 87 (1994), S. 578-585 
    Details
    ISSN: 1432-0533
    Keywords: Amyotrophic lateral sclerosis ; Motor cortex ; Betz cells ; Immunocytochemistry ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract This report concerns an immunocytochemical and ultrastructural study of the motor cortices of 11 patients with amyotrophic lateral sclerosis (ALS). Specimens from 12 normal individuals served as controls. Antibodies against phosphorylated neurofilament (PNF; 200 kDa), ubiquitin, glial fibrillary acidic protein (GFAP) and phosphorylated tau protein were used. The pyramidal cells of layer III of all ALS patients were stained, with varying intensities, by the antibody to PNF. By contrast, Betz cells reacted less frequently with this antibody. Staining for GFAP was noted in numerous astrocytes in layer III and at the transition between white matter and motor cortex of most patients. Ubiquitin-positive inclusions were only occasionally seen in Betz cell and pyramidal cell of layer V. These observations indicate that alterations of the motor cortex occur first in the pyramidal cells of layer III rather than in Betz cells. Pyramidal cells and Betz cells were not stained by the antibody to phosphorylated tau protein. In controls, pyramidal cells and Betz cells were less frequently stained with the anti-neurofilament antibody than those from ALS patients. Immunoreactivity of GFAP in layer III and at the junction of white matter and motor cortex was observed in only one patient. Ultrastructural examination revealed that the Betz cells of some ALS patients had Bunina bodies (BB), Lewy body-like inclusions (LBI) and skein-like inclusions (SI), as well as bundles of filaments that were thicker than neurofilaments; some of these filaments appeared to be constricted. The incidence of these inclusions was lower than that seen in anterior horn neurons. Cytoplasmic inclusions such as BB, LBI, and SI were not observed in any of the controls. Our findings suggest that the cytopathology of upper motor neurons is similar to that of lower motor neurons and that the changes seen in Betz cells appear to be a reflection of the lower motor neuron alterations.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00293318
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  • 12
    Electronic Resource
    Electronic Resource
    Astrocytic straight tubules in the brain of a patient with Pick's disease (1994)
    Springer
    Acta neuropathologica 88 (1994), S. 587-591 
    Details
    ISSN: 1432-0533
    Keywords: Astrocytes ; Electron microscopy ; Immunocytochemistry ; Pick's disease ; Straight tubules
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract This report concerns an immunohistochemical and ultrastructural study of cerebral astrocytes in a patient with Pick's disease of 20 years' duration. The autopsied brain was prominently small (710 g) with marked fronto-temporal lobar atrophy. Histological examination demonstrated profound neuronal loss and spongy changes with tau-positive Pick bodies in the frontal and temporal cortex. In addition, many glial cells in the temporal lobe white matter contained round to oval, argentophilic and slightly hematoxinophilic cytoplasmic inclusions that were also immunolabeled with the anti-tau antibody. On electron microscopy, the glial inclusions were observed in the perikarya of astrocytes that were recognized as such from intracytoplasmic glial filaments and the presence of gap junctions. The inclusions were free in the cytoplasm, without a limiting membrane, and mainly comprised irregular aggregations of bundles of about 15-nm straight tubules, which were indistinguishable from those of intraneuronal Pick bodies. Furthermore, various patterns of accumulation of the same straight tubules were frequently noted in perivascular astrocytic processes carrying a basal lamina. These findings indicate that in Pick's disease astrocytes are also affected by a similar insult to that which affects neurons.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00296498
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  • 13
    Electronic Resource
    Electronic Resource
    Neuronal vacuole formation in the rat posterior cingulate/retrosplenial cortex after treatment with the N -methyl-D-aspartate (NMDA) antagonist MK-801 (dizocilpine maleate) (1994)
    Springer
    Acta neuropathologica 88 (1994), S. 511-519 
    Details
    ISSN: 1432-0533
    Keywords: Key words Vacuolization ; Neurotoxicity ; Neuropathology ; Electron microscopy ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Cytoplasmic vacuoles appear in neurons of the posterior cingulate/retrosplenial cortex (PC/RS) of rats after treatment with N-methyl-D-aspartate (NMDA) receptor antagonists. Prominent dilatation of mitochondria and endoplasmic reticulum has been described within 2 h; however, the ultrastructural features of vacuole formation are unknown. To investigate this, the present study examined the PC/RS cortex of male rats (age 60 – 70 days) at 15, 30, 45, 60, 90, and 120 min after subcutaneous treatment with 1 mg/kg of the noncompetitive NMDA antagonist MK-801 (dizocilpine maleate, 5-methyl-10, 11-dihydro-5H-dibenzo [a,d] cyclohepten-5,10-imine). Subtle mitochondrial dilatation was identified in a few neurons as early as 15 min postdose (MPD). By 30 MPD, dilatation was more pronounced in mitochondria and also involved the endoplasmic reticulum and perinuclear space. Ribosomal disaggregation and degranulation were also evident by 30 MPD. At all subsequent time points, dilatation of mitochondria and endoplasmic reticulum progressed in severity. Although the relative involvement of mitochondria and endoplasmic reticulum varied, glia were not involved. These ultrastructural data suggest that after treatment with MK-801, mitochondrial dilatation precedes involvement of endoplasmic reticulum in vacuolization of susceptible PC/RS cortical neurons. The early mitochondrial effects identified in this study suggest an initial metabolic insult that rapidly progresses to affect endoplasmic reticulum and ribosomes. This strengthens the relationship between the ability of certain NMDA antagonists to induce energy perturbations and neuronal vacuoles in the same region of the rat cerebral cortex.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00296487
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  • 14
    Electronic Resource
    Electronic Resource
    An ultrastructural analysis of human post-infectious (allergic) encephalomyelitis (1994)
    Springer
    Acta neuropathologica 87 (1994), S. 541-544 
    Details
    ISSN: 1432-0533
    Keywords: Allergic Encephalomyelitis ; Astrocytes ; Demyelination ; Electron microscopy ; Multiple sclerosis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract A 6-year-old boy developed post-infectious encephalomyelitis and underwent a brain biopsy (10 days after the onset of neurologic symptoms). Electron microscopic analysis of brain showed demyelinated axons, thinly myelinated axons, aberrant remyelination, and numerous phagocytes containing myelin debris. Physical stripping of myeling by pseudopodial extensions of macrophages, as reported in experimental allergic encephalomyelitis, was noted. Hypertrophic and hyperplastic astrocytes were prominent among the phagocytic cells and played an unexpectedly active role in demyelination.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00294183
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  • 15
    Electronic Resource
    Electronic Resource
    Immunocytochemical and ultrastructural studies of the motor cortex in amyotrophic lateral sclerosis (1994)
    Springer
    Acta neuropathologica 87 (1994), S. 578-585 
    Details
    ISSN: 1432-0533
    Keywords: KeyWordsAmyotrophic lateral sclerosis ; Motor cortex Betz cells ; Immunocytochemistry ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract This report concerns an immunocytochemical and ultrastructural study of the motor cortices of 11 patients with amyotrophic lateral sclerosis (ALS). Specimens from 12 normal individuals served as con- trols. Antibodies against phosphorylated neurofilament (PNF; 200 kDa), ubiquitin, glial fibrillary acidic protein (GFAP) and phosphorylated tau protein were used. The pyramidal cells of layer III of all ALS patients were stained, with varying intensities, by the antibody to PNF. By contrast, Betz cells reacted less frequently with this antibody. Staining for GFAP was noted in numerous astrocytes in layer III and at the transition between white matter and motor cortex of most patients. Ubiquitin-positive inclusions were only occasionally seen in Betz cell and pyramidal cell of layer V. These observations indicate that alterations of the motor cortex occur first in the pyramidal cells of layer III rather than in Betz cells. Pyramidal cells and Betz cells were not stained by the antibody to phosphorylated tau protein. In controls, pyramidal cells and Betz cells were less frequently stained with the anti-neurofilament antibody than those from ALS patients. Immunoreactivity of GFAP in layer III and at the junction of white matter and motor cortex was observed in only one patient. Ultrastructural examination revealed that the Betz cells of some ALS patients had Bunina bodies (BB), Lewy body-like inclusions (LBI) and skein-like inclusions (SI), as well as bundles of filaments that were thicker than neurofilaments; some of these filaments appeared to be constricted. The incidence of these inclusions was lower than that seen in anterior horn neurons. Cytoplasmic inclusions such as BB, LBI, and SI were not observed in any of the controls. Our findings suggest that the cytopathology of upper motor neurons is similar to that of lower motor neurons and that the changes seen in Betz cells appear to be a reflection of the lower motor neuron alterations.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00293318
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  • 16
    Electronic Resource
    Electronic Resource
    Generalised nuclear and cytoplasmic inclusion disease: a rare case investigated by microscopy and immunohistochemistry (1994)
    Springer
    Acta neuropathologica 87 (1994), S. 648-654 
    Details
    ISSN: 1432-0533
    Keywords: Inclusion body disease ; Electron microscopy ; Immunohistochemistry ; Viral infection ; Primary metabolic disorder
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract A Caucasian female who was noted to be mildly microcephalic at birth was diagnosed as having cerebral palsy at the age of 1 year. Her development was delayed and she never walked or talked. She appeared relatively stable neurologically until the age of 17 years when she had an illness with fever thought to be due to a virus. She was noted to deteriorate from this time on until her death at the age of 19 years. Autopsy revealed intranuclear and cytoplasmic inclusions widespread throughout the brain and visceral organs. There was no evidence of inflammation. Immunohistochemistry revealed strong immunoreactivity for tau protein and neurofilament protein. Electron microscopy revealed the inclusions to be composed of homogeneous finely granular material. Scattered with the granular material in the cytoplasmic bodies were crystalline structures with a honeycomb appearance. The possibility of these changes representing an old viral infection or a primary metabolic disorder are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00293327
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  • 17
    Electronic Resource
    Electronic Resource
    Light and electron microscopic study of omental milky spots in New Zealand Black mice, with special reference to the extramedullary hematopoiesis (1994)
    Springer
    Anatomy and embryology 189 (1994), S. 215-226 
    Details
    ISSN: 1432-0568
    Keywords: Omental milky spot ; Megakaryocyte ; Myelopoiesis ; Electron microscopy ; New Zealand Black mouse
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Omental milky spots are especially large and numerous in New Zealand Black (NZB) mice, which are known to develop spontaneous autoimmune diseases. We investigated omental milky spots in NZB mice by light and electron microscopy. The milky spots were composed of abundant lymphocytes/plasma cells with macrophages, neutrophils, eosinophils, megakaryocytes, and various stromal cells. In addition, clustered neutrophils in various maturation stages with occasional mitotic figures were frequently present in the milky spots: apparent neutrophilic myelopoiesis was present. The presence of megakaryocytes was sporadic. Considering the giant size of megakaryocytes, their direct migration into the milky spots from the bone marrow or spleen seems improbable. Thus, the presence of megakaryocytes was interpreted as probable megakaryopoiesis. Erythroblasts were not contained in the milky spots. These findings seem to indicate that the milky spots in NZB mice represent a special type of lymphoid tissue with active neutrophilic myelopoiesis and probable megakaryopoiesis. Reticulum cells in the milky spots in NZB mice had well-developed dense bodies consisting of clustered parallel tubules that showed a hexagonal array. However, the biological significance of these cells remains unknown.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00239009
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  • 18
    Electronic Resource
    Electronic Resource
    Fiber composition of the lateral plantar and superficial peroneal nerves in the rat foot (1994)
    Springer
    Anatomy and embryology 189 (1994), S. 393-399 
    Details
    ISSN: 1432-0568
    Keywords: Rat ; Myelinated axons ; C-fibers ; Skin ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract This study examines the fiber composition of two nerves projecting to the rat hindpaw: the lateral plantar nerve (LPN), which innervates plantar glabrous skin and some plantar muscles, and the foot branch of the superficial peroneal nerve (fSPN), which projects to dorsal hairy skin. The LPN contains 872 (33%) myelinated axons with a size range of 1–7 μm and a peak at 4 μm. Some 200 of the myelinated axons are muscle efferents. There are 1,969 (67%) C-fibers. After neonatal capsaicin treatment, the number of C-fibers in the LPN is 61% below the normal level, but it is not significantly different from control levels after chemical sympathectomy with guanethidine. The fSPN is composed of 470 (20%) myelinated axons with a size range similar to that in the LPN. Virtually all myelinated fibers are sensory. There are 1,791 (80%) C-fibers. In neonatally capsaicin-treated animals, the occurrence of C-fibers is 65% below control levels. In chemically sympathectomized animals, the number of C-fibers in the fSPN is normal. This description of the fiber composition of the LPN and the fSPN in the rat provides a basis for future experimental studies.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00185434
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  • 19
    Electronic Resource
    Electronic Resource
    Astrocytic straight tubules in the brain of a patient with Pick's disease (1994)
    Springer
    Acta neuropathologica 88 (1994), S. 587-591 
    Details
    ISSN: 1432-0533
    Keywords: Key words Astrocytes ; Electron microscopy ; Immunocytochemistry ; Pick's disease ; Straight tubules
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract This report concerns an immunohistochemical and ultrastructural study of cerebral astrocytes in a patient with Pick's disease of 20 years' duration. The autopsied brain was prominently small (710   g) with marked fronto-temporal lobar atrophy. Histological examination demonstrated profound neuronal loss and spongy changes with tau-positive Pick bodies in the frontal and temporal cortex. In addition, many glial cells in the temporal lobe white matter contained round to oval, argentophilic and slightly hematoxinophilic cytoplasmic inclusions that were also immunolabeled with the anti-tau antibody. On electron microscopy, the glial inclusions were observed in the perikarya of astrocytes that were recognized as such from intracytoplasmic glial filaments and the presence of gap junctions. The inclusions were free in the cytoplasm, without a limiting membrane, and mainly comprised irregular aggregations of bundles of about 15-nm straight tubules, which were indistinguishable from those of intraneuronal Pick bodies. Furthermore, various patterns of accumulation of the same straight tubules were frequently noted in perivascular astrocytic processes carrying a basal lamina. These findings indicate that in Pick's disease astrocytes are also affected by a similar insult to that which affects neurons.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00296498
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  • 20
    Electronic Resource
    Electronic Resource
    Cytoplasmic inclusions of astrocytic elements of glial tumors: special reference to round granulated body and eosinophilic hyaline droplets (1994)
    Springer
    Acta neuropathologica 88 (1994), S. 501-510 
    Details
    ISSN: 1432-0533
    Keywords: Round granulated body ; Eosinophilic hyaline droplets ; Astrocytic tumors ; Immunohistochemistry ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Round granulated body (RGB) and eosinophilic hyaline droplets (EHDs) have been described as cytoplasmic inclusions of certain astrocytic tumors. In the previous literature, however, these inclusions have been described using various terms or regarded as nosologically the same entity. Light microscopically, RGB apeared as a round discrete body filled with fine uniform granules, while EHDs demonstrated a cluster of bright eosinophilic, round objects of various size. They could be clearly distinguished even by conventional histochemical staining such as the Masson trichrome stain and the phosphotungstic acid hematoxylin preparation. Both RGB and EHDs expressed positive immunoreactions for glial fibrillary acidic protein, several lysosomal markers, and some stress-response proteins. The ultrastructural appearances of these inclusions were distinct, however, one common feature was that they consisted of aggregations of numerous membrane-bound electron-dense bodies. Thus, both inclusions appear to be produced by neoplastic astrocytes and are possibly related to the lysosomal system. We examined the presence of RGB and EHDs in 138 astrocytic tumors. Both inclusions occurred most frequently in pleomorphic xanthoastrocytomas, followed by gangliogliomas and pilocytic astrocytomas. Subependymal giant cell astrocytomas exhibited only RGBs. RGBs and EHDs were not seen in any abundance in glioblastomas, gliosarcomas, fibrillary astrocytomas, protoplasmic astrocytomas, or oligo-astrocytomas. Some glioblastomas, however, showed only EHDs in small numbers. Several anaplastic astrocytomas were associated with a large number of RGBs and/or EHDs, and they revealed only rare mitosis despite marked cellular pleomorphism. Although RGB and EHDs have different morphological features, the presence of these inclusions in abundance may represent either a degenerative change, a long-standing lesion, or an indolent growth of the astrocytic tumors.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00296486
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  • 21
    Electronic Resource
    Electronic Resource
    Fine structure of the retinal pigment epithelium in the Port Jackson shark (Heterodontus phillipi) (1994)
    Springer
    Anatomy and embryology 190 (1994), S. 501-506 
    Details
    ISSN: 1432-0568
    Keywords: Retinal pigment epithelium (RPE) ; Electron microscopy ; Elasmobranch ; Heteterodontus phillipi
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The structure of the retinal epithelium (RPE), choriocapillaris and Bruch's membrane (complexus basalis) has been studied by light and electron microscopy in the Port Jackson shark (Heterodontus phillipi). In this elasmobranch the RPE consists of a single layer of low cuboidal cells which show basal (scleral) infoldings and apical (vitreal) processes that enclose photoreceptor outer segments. Laterally these epithelial cells are joined by a series of apically located tight junctions. The RPE cells display a large vesicular nucleus, abundant smooth endoplasmic reticulum as well as numerous polysomes and mitochondria. Phagosomes are present, rough endoplasmic reticulum is scarce and myeloid bodies were not observed. Melanosomes are absent over the choroidally located tapetum lucidum, but are not abundant even in extratapetal areas. This paucity of melanosomes probably makes retinomotor movements unimportant. Bruch's membrane or complexus basalis is a pentalaminate structure. The endothelium of the choriocapillaris is thin but minimally fenestrated.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00235498
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  • 22
    Electronic Resource
    Electronic Resource
    Fine structure of the choroidal tapetum lucidum in the Port Jackson shark (Heterodontus phillipi) (1994)
    Springer
    Anatomy and embryology 190 (1994), S. 591-596 
    Details
    ISSN: 1432-0568
    Keywords: Tapetum lucidum ; Electron microscopy ; Elasmobranch ; Heterodontus phillipi
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The choroidally located tapetum lucidum of the Port Jackson shark (Heterodontus phillipi) was examined by light and electron microscopy in light-adapted specimens. In this species the tapetum consists of a single layer of overlapping cells oriented at an angle of about 30° to the incoming light and situated immediately external to the choriocapillaris. These tapetal cells alternate with and are separated from one another by melanocytes which extend beyond the tapetal cells to intervene between the tapetal cells and the incoming light. The tapetal cells and the melanocytes are flattened plate-like cells with their widest dimension facing the retina. Internally the tapetal cells display a peripherally located vesicular nucleus with most organelles in a paranuclear location. The bulk of a tapetal cell is packed with regularly spaced crystals reported to be guanine. The size and spacing of these reflective crystals is commensurate with the principles of constructive interference. In light adaptation, the melanosomes of the intervening melanocytes are widely dispersed and for the most part block the passage of light to the tapetal cells. Although dark-adapted specimens were not available, it seems reasonable to assume that in dark adaptation these melanosomes will retreat to unmask the tapetum and allow it to function as a known reflective layer.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00190109
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  • 23
    Electronic Resource
    Electronic Resource
    Distribution of apoptosis-mediating Fas antigen in human skin and effects of anti-Fas monoclonal antibody on human epidermal keratinocyte and squamous cell carcinoma cell lines (1994)
    Springer
    Archives of dermatological research 286 (1994), S. 396-407 
    Details
    ISSN: 1432-069X
    Keywords: Fas antigen ; Immunohistochemical ; Skin disease ; Keratinocytes ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Fast antigen is a cell surface protein that mediates apoptosis. Using immunohistological, flow cytometry and electron microscopic analyses, we investigated the expression of Fas antigen on various skin tissues, and on cultured SV40-transformed human epidermal keratinocyte cell line KJD and human skin squamous cell carcinoma cell line HSC. The Fas antigen was widely distributed in skin components such as the keratinocytes in the lower portion of the epidermis, epidermal dendritic cells, endothelial cells, fibroblasts, apocrine glands, eccrine sweat glands, sebaceous glands, some normal melanocytes and infiltrating lymphoid cells. It was also strongly expressed on the keratinocytes of lichenoid eruptions seen in lupus erythematosus and lichen planus, and on the spongiotic or acanthotic epidermis seen in chronic eczema, adult T-cell leukaemia/lymphoma (ATLL) and atopic dermatitis. Its expression was closely correlated with lymphoid infiltrating cells and it was strongly expressed in lymphoid neoplastic cells, particularly ATLL cells, and fibroblasts seen in dermatofibroma. However, the antigen was not detected on basal cell epithelioma cells, some malignant melanomas or any junctional naevi. The cell lines KJD and HSC strongly expressed the Fas antigen, and crosslinking of the Fas antigen by an anti-Fas monoclonal antibody induced apoptosis of these cell lines. These results indicate that the apoptosis-mediating Fas antigen may play an important role in normal skin turnover and cell differentiation, in immune regulation of skin tumours, and in the pathogenesis of various skin diseases.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00371800
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  • 24
    Electronic Resource
    Electronic Resource
    Synaptic connectivity of serotonin graft efferents in the suprachiasmatic and supraoptic nuclei of the hypothalamus (1994)
    Springer
    Experimental brain research 101 (1994), S. 353-364 
    Details
    ISSN: 1432-1106
    Keywords: Transplantation ; Serotonin neurons ; Hypothalamus ; Electron microscopy ; Rat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract We have previously reported that a cell suspension from the rostral part of the embryonic raphe grafted to the basal hypothalamus of 5,7-dihydroxytryptamine-denervated rats produced incomplete serotonin (5-HT) re-innervation of the suprachiasmatic nucleus (SCN) as opposed to hyper-innervation of the supraoptic nucleus (SON). We took advantage of this experimental model to investigate whether the graft-derived, 5-HT fibres retained normal ultrastructural features, and, particularly, a normal density of synaptic junctions, irrespective of the extent of target re-innervation. The intrinsic features of immunostained, graft-derived 5-HT axonal varicosities in both the SCN (ventral portion) and the SON were essentially similar to those exhibited by the respective endogenous innervation. Analysis of well-preserved varicosities in uninterrupted series of thin sections allowed us to evaluate directly the proportions of junctional to non-junctional 5-HT varicosities in both regions. Synaptic incidences were also remarkably conserved after grafting (45.5% in the SCN versus 38.5% in the SON; 48% and 38% in normal rats, respectively). Synapses were primarily reestablished on dendritic shafts, which also were identified as the major post-synaptic targets of the normal 5-HT innervations. We noted, however, a tendency toward increased numbers of symmetrical versus asymmetrical synapses in both the SCN and SON of grafted rats. Thus, irrespective of whether hypo-or hyper-innervation patterns developed post-grafting, the transplanted 5-HT neurons essentially retained normal ultrastructural features in their target territories, with a normal incidence of synaptic junctions. The data provide further support to the hypothesis that the innervation territory is the major determinant of the frequency with which ingrowing 5-HT fibres make synaptic junctions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00227329
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  • 25
    Electronic Resource
    Electronic Resource
    Ammonium-excreting Azospirillum sp. become intracellularly established in maize (Zea mays) para-nodules (1994)
    Springer
    Biology and fertility of soils 17 (1994), S. 1-8 
    Details
    ISSN: 1432-0789
    Keywords: Ammonium excretion ; Azospirillum brasilense ; Auxine ; 2,4-Dichlor-phenoxy-acetic acid ; Nitrogen fixation ; Paranodulation ; Maize ; Zea mays ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Geosciences , Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition
    Notes: Abstract Maize seedlings develop nodule-like tumour knots (para-nodules) along primary roots when treated with the auxin 2,4-dichlor-phenoxy-acetic acid (2,4-D). Inoculated NH 4 + -excreting Azospirillum brasilense cells were shown to colonize these tumours, mostly intracellularly, promoting a high level of N2 fixation when microaerophilic conditions were imposed. The nitrogenase activity inside the para-nodules was less sensitive to free O2 than in non-para-nodulating roots. Both light and electron microscopy showed a dense bacterial population inside intact tumour cells, with the major part of the cell infection along a central tumour tissue. The bacteria colonized the cytoplasm with a close attachment to inner cell membranes. In an auxin-free growth medium, young 2,4-D-induced para-nodules grew further to become mature differentiated root organs in which introduced bacteria survived with a stable population. These results provide evidence that gramineous plants are potentially able to create a symbiosis with diazotrophic bacteria in which the NH 4 + -excreting symbiont will colonize para-nodule tissue intracellularly, thus becoming well protected.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00418663
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  • 26
    Electronic Resource
    Electronic Resource
    Ultrastructure of an extreme thermophilic hydrogen-oxidizing bacterium Calderobacterium hydrogenophilum (1994)
    Springer
    Archives of microbiology 162 (1994), S. 267-271 
    Details
    ISSN: 1432-072X
    Keywords: Key words     Extremely thermophilic eubacterium ; Calderobacterium hydrogenophilium ; Ultrastructure ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract       Calderobacterium hydrogenophilum is an extreme thermophilic, obligately chemoautotrophic, hydrogen-oxidizing bacterium. The cells were shown to be non-motile straight rods of average size 0.4 × 2.5 μm. After negative-staining of the whole cells, no flagella were observed. The multilayered cell wall was of type 1 and possessed a crystalline proteinaceous surface layer exhibiting p4 symmetry. The square unit cells had a lattice constant of approximately 11 nm. Cell division occurred by a constriction mechanism. C. hydrogenophilum differred from a similar hydrogen-oxidizing eubacterium, Hydrogenobacter thermophilus, by the absence of intracytoplasmic membrane structures in chemically fixed cells. However, an electron-dense intracytoplasmic hemispherical structure adhering to the inner membrane was frequently observed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00301849
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  • 27
    Electronic Resource
    Electronic Resource
    Ultrastructure of an extreme thermophilic hydrogen-oxidizing bacterium Calderobacterium hydrogenophilum (1994)
    Springer
    Archives of microbiology 162 (1994), S. 267-271 
    Details
    ISSN: 1432-072X
    Keywords: Extremely thermophilic eubacterium ; Calderobacterium hydrogenophilium ; Ultrastructure ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Calderobacterium hydrogenophilum is an extreme thermophilic, obligately chemoautotrophic, hydrogen-oxidizing bacterium. The cells were shown to be nonmotile straight rods of average size 0.4x2.5 μm. After negative-staining of the whole cells, no flagella were observed. The multilayered cell wall was of type 1 and possessed a crystalline proteinaceous surface layer exhibiting p4 symmetry. The square unit cells had a lattice constant of approximately 11 nm. Cell division occurred by a constriction mechanism. C. hydrogenophilum differred from a similar hydrogen-oxidizing eubacterium, Hydrogenobacter thermophilus, by the absence of intracytoplasmic membrane structures in chemically fixed cells. However, an electron-dense intracytoplasmic hemispherical structure adhering to the inner membrane was frequently observed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00301849
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  • 28
    Electronic Resource
    Electronic Resource
    Membrane topology of insulin receptors reconstituted into lipid vesicles (1994)
    Springer
    The journal of membrane biology 140 (1994), S. 215-223 
    Details
    ISSN: 1432-1424
    Keywords: Insulin receptor ; Membrane reconstitution ; Electron microscopy ; Quaternary structure ; Immunogold labeling
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Insulin receptors were incorporated into liposomes by two different procedures, one using dialysis and one using detergent removal by Bio-Beads. Receptor incorporation was analyzed by gradient centrifugation and electron microscopy. Reconstituted receptors projected up to 12 nm above the membrane and exhibited a T-shaped structure compatible with that previously described for the solubilized receptor. Insulin binding and autophosphorylation experiments indicated that approx. 50% of the receptors were incorporated right-side out. Such random orientation was confirmed by immunogold labeling of the α- and the β-subunit of the receptor. Immunogold labeling of the C-terminus of the β-subunit indicates that it resides about 6 nm off the membrane, while two α-subunit epitopes were labeled at about twice this distance, confirming that the α-subunit is harbored in the cross-bar of the T-structure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00233710
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  • 29
    Electronic Resource
    Electronic Resource
    Astrocytes alter their polarity in organotypic slice cultures of rat visual cortex (1994)
    Springer
    Cell & tissue research 277 (1994), S. 557-564 
    Details
    ISSN: 1432-0878
    Keywords: Key words: Slice culture ; Cerebral cortex ; Astrocytes ; Orthogonal arrays of particles - Freeze-fracture ; Electron microscopy ; Rat (Lewis)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract. The ultrastructure of astrocytes in an organotypic slice culture of the rat visual cortex was investigated using ultrathin sections and freeze-fracture replicas. After a culture period of 9–15 days, a glial scaffold formed that separated the bulk of the slice neuropil from the medium and the underlying plasma clot. However, the glial cells and processes did not build a dense barrier but allowed the outgrowth of neurites. A basal lamina covering the medium-oriented surface of the astrocytes was not found. In freeze-fracture replicas, orthogonal arrays of particles (OAP) were characteristic components of astrocytic membranes. The OAP density in membranes bordering the medium was 35±13 OAP/μm2, corresponding to 2.5% of this membrane area; the OAP density in membranes within the slice neuropil was 22±12 OAP/μm2, corresponding to 1.4% of this membrane area. Although the difference was significant, it was greatly reduced when comparing OAP densities in endfoot and non-endfoot membranes in vivo. Another mode of polarity was recognized in astrocytes of the organotypic slice culture. In membranes of astrocytes bordering upon the medium, the density of non-OAP intramembranous particles (IMP) was clearly higher (1130±136 IMP/μm2) than in membranes of astrocytes in the center of the slice (700±172 IMP/μm2). This pronounced IMP-related polarity was observed neither in vivo nor in cultured astrocytes. The present study suggests, together with data from the literature, that the distribution of astrocytic OAP across the cell surface is influenced by the existence of a basal lamina and neuronal activity, and that astrocytes possess a more remarkable plasticity of membrane structure than previously suspected.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00300229
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  • 30
    Electronic Resource
    Electronic Resource
    Organization of the endoplasmic reticulum in renal cell lines MDCK and LLC-PK1 (1994)
    Springer
    Cell & tissue research 277 (1994), S. 297-307 
    Details
    ISSN: 1432-0878
    Keywords: Endoplasmic reticulum ; Cellular transport ; Mitochondria ; Electron microscopy ; Contocal microscopy ; MDCK cells ; LLC-PK1 cells
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract The spatial organization of the endoplasmic reticulum has been studied in two renal cell lines, MDCK and LLC-PK1, which originate from the distal and proximal portions of the mammalian nephron, respectively, and which form a polarized epithelium when they reach confluence in tissue culture. The two renal cell lines, grown to confluence on either solid or permeable supports, were investigated by fluorescence microscopy, confocal microscopy, and transmission electron microscopy. Fluorescence labeling of the endoplasmic reticulum was achieved using the cationic fluorescent dye DIOC6 (3). In order to differentiate fluorescent labeling of the endoplasmic reticulum from that of the mitochondria, cells were also labeled with rhodamine 123. For electron microscopy, the spatial organization of the endoplasmic reticulum was examined in thick sections using the long-duration osmium impregnation technique or the ferrocyanide/osmium technique. In both cell lines, the endoplasmic reticulum formed an abundant tubular network of canaliculi that frequently abutted the basolateral domain of the plasma membrane and occasionally the apical membrane. Elements of the endoplasmic reticulum were also found in close proximity to mitochondria that, as in the nephron, formed branched structures. Canaliculi appeared circular or flattened and had an inner diameter of 10–70 nm for MDCK cells and 20–90 nm for LLC-PK1 cells. Such a three-dimensional organization might facilitate the translocation of defined lipid species between the endoplasmic reticulum and the plasma membrane, and between the endoplasmic reticulum and mitochondria.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00327777
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  • 31
    Electronic Resource
    Electronic Resource
    Organization of the endoplasmic reticulum in renal cell lines MDCK and LLC-PK1 (1994)
    Springer
    Cell & tissue research 277 (1994), S. 297-307 
    Details
    ISSN: 1432-0878
    Keywords: Key words: Endoplasmic reticulum ; Cellular transport ; Mitochondria ; Electron microscopy ; Confocal microscopy ; MDCK cells ; LLC-PK1 cells
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract. The spatial organization of the endoplasmic reticulum has been studied in two renal cell lines, MDCK and LLC-PK1, which originate from the distal and proximal portions of the mammalian nephron, respectively, and which form a polarized epithelium when they reach confluence in tissue culture. The two renal cell lines, grown to confluence on either solid or permeable supports, were investigated by fluorescence microscopy, confocal microscopy, and transmission electron microscopy. Fluorescence labeling of the endoplasmic reticulum was achieved using the cationic fluorescent dye DIOC6 (3). In order to differentiate fluorescent labeling of the endoplasmic reticulum from that of the mitochondria, cells were also labeled with rhodamine 123. For electron microscopy, the spatial organization of the endoplasmic reticulum was examined in thick sections using the long-duration osmium impregnation technique or the ferrocyanide/osmium technique. In both cell lines, the endoplasmic reticulum formed an abundant tubular network of canaliculi that frequently abutted the basolateral domain of the plasma membrane and occasionally the apical membrane. Elements of the endoplasmic reticulum were also found in close proximity to mitochondria that, as in the nephron, formed branched structures. Canaliculi appeared circular or flattened and had an inner diameter of 10–70 nm for MDCK cells and 20–90 nm for LLC-PK1 cells. Such a three-dimensional organization might facilitate the translocation of defined lipid species between the endoplasmic reticulum and the plasma membrane, and between the endoplasmic reticulum and mitochondria.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004410050156
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  • 32
    Electronic Resource
    Electronic Resource
    Progressive reorganization of the myenteric plexus during one year following reanastomosis of the ileum of the guinea pig (1994)
    Springer
    Cell & tissue research 277 (1994), S. 259-272 
    Details
    ISSN: 1432-0878
    Keywords: Key words: Ileum ; Transection ; Reanastomosis ; Myenteric plexus ; NADH diaphorase histochemistry ; Neuron-specific enolase ; Electron microscopy ; Guinea pig
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract. The enteric nervous system appears to play a pivotal role in the functional recovery of the gastrointestinal tract after partial resection and reanastomosis, but the structural changes following surgery are not fully understood. The present study was designed to clarify the processes of myenteric plexus regeneration up to one year after transection and reanastomosis of the ileum of the guinea pig. The following techniques were used: nicotinamide adenine dinucleotide (NADH) diaphorase histochemistry, immunostaining of neuron-specific enolase (NSE) in whole-mount preparations, and transmission electron microscopy. Two months after transection and reanastomosis, myenteric ganglion cells with NADH diaphorase reactions were scarce in the center of the lesion, and were less numerous in adjacent areas (3 mm in width) than in the control ileum. In the areas adjacent to the lesion, a few large extraganglionic neurons that did not completely compensate for the loss of ganglion neurons were observed. The remaining ileum showed no changes in NADH diaphorase staining pattern at this stage. Two to 12 months after transection and reanastomosis, ectopic large neurons gradually increased in number not only in the areas adjacent to the lesion but also in part of the remaining ileum, up to 10 cm from the lesion. Concomitantly, large ganglion neurons decreased in number in these areas. In other ileal regions (more than 10 cm distant from the site of transection), no obvious changes in NADH diaphorase staining were noted throughout the observation period. The outgrowth of NSE-containing nerve fibers from the severed stumps was seen two weeks after transection. Six weeks later, numerous bundles of fine nerve fibers with NSE were shown to interconnect the oral and anal cut ends of the myenteric plexus, but they exhibited no subsequent alterations. Transmission electron microscopy revealed that regenerating nerve fiber bundles appeared initially among irregularly arranged smooth muscle cells eight weeks after the operation, as expected from light-microscopic observations. These findings suggest that myenteric ganglion cell bodies, unlike myenteric nerve fibers, require a longer term of reconstruction than previously believed after transection and reanastomosis of the ileum of the guinea pig.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004410050153
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  • 33
    Electronic Resource
    Electronic Resource
    Progressive reorganization of the myenteric plexus during one year following reanastomosis of the ileum of the guinea pig (1994)
    Springer
    Cell & tissue research 277 (1994), S. 259-272 
    Details
    ISSN: 1432-0878
    Keywords: Ileum ; Transection ; Reanastomosis ; Myenteric plexus ; NADH diaphorase histochemistry ; Neuron-specific enolase ; Electron microscopy ; Guinea pig
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract The enteric nervous system appears to play a pivotal role in the functional recovery of the gastrointestinal tract after partial resection and reanastomosis, but the structural changes following surgery are not fully understood. The present study was designed to clarify the processes of myenteric plexus regeneration up to one year after transection and reanastomosis of the ileum of the guinea pig. The following techniques were used: nicotinamide adenine dinucleotide (NADH) diaphorase histochemistry, immunostaining of neuron-specific enolase (NSE) in whole-mount preparations, and transmission electron microscopy. Two months after transection and reanastomosis, myenteric ganglion cells with NADH diaphorase reactions were scarce in the center of the lesion, and were less numerous in adjacent areas (3 mm in width) than in the control ileum. In the areas adjacent to the lesion, a few large extraganglionic neurons that did not completely compensate for the loss of ganglion neurons were observed. The remaining ileum showed no changes in NADH diaphorase staining pattern at this stage. Two to 12 months after transection and reanastomosis, ectopic large neurons gradually increased in number not only in the areas adjacent to the lesion but also in part of the remaining ileum, up to 10 cm from the lesion. Concomitantly, large ganglion neurons decreased in number in these areas. In other ileal regions (more than 10 cm distant from the site of transection), no obvious changes in NADH diaphorase staining were noted throughout the observation period. The outgrowth of NSE-containing nerve fibers from the severed stumps was seen two weeks after transection. Six weeks later, numerous bundles of fine nerve fibers with NSE were shown to interconnect the oral and anal cut ends of the myenteric plexus, but they exhibited no subsequent alterations. Transmission electron microscopy revealed that regenerating nerve fiber bundles appeared initially among irregularly arranged smooth muscle cells eight weeks after the operation, as expected from light-microscopic observations. These findings suggest that myenteric ganglion cell bodies, unlike myenteric nerve fibers, require a longer term of reconstruction than previously believed after transection and reanastomosis of the ileum of the guinea pig.
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    URL: http://dx.doi.org/10.1007/BF00327773
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  • 34
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    Electronic Resource
    Astrocytes alter their polarity in organotypic slice cultures of rat visual cortex (1994)
    Springer
    Cell & tissue research 277 (1994), S. 557-564 
    Details
    ISSN: 1432-0878
    Keywords: Slice culture ; Cerebral cortex ; Astrocytes ; Orthogonal arrays of particles ; Freeze-fracture ; Electron microscopy ; Rat (Lewis)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract The ultrastructure of astrocytes in an organotypic slice culture of the rat visual cortex was investigated using ultrathin sections and freeze-fracture replicas. After a culture period of 9–15 days, a glial scaffold formed that separated the bulk of the slice neuropil from the medium and the underlying plasma clot. However, the glial cells and processes did not build a dense barrier but allowed the outgrowth of neurites. A basal lamina covering the medium-oriented surface of the astrocytes was not found. In freeze-fracture replicas, orthogonal arrays of particles (OAP) were characteristic components of astrocytic membranes. The OAP density in membranes bordering the medium was 35±13 OAP/μm2, corresponding to 2.5% of this membrane area; the OAP density in membranes within the slice neuropil was 22±12 OAP/μ2, corresponding to 1.4% of this membrane area. Although the difference was significant, it was greatly reduced when comparing OAP densities in endfoot and non-endfoot membranes in vivo. Another mode of polarity was recognized in astrocytes of the organotypic slice culture. In membranes of astrocytes bordering upon the medium, the density of non-OAP intramembranous particles (IMP) was clearly higher (1130±136 IMP/ μm2) than in membranes of astrocytes in the center of the slice (700±172 IMP/μm2). This pronounced IMP-related polarity was observed neither in vivo nor in cultured astrocytes. The present study suggests, together with data from the literature, that the distribution of astrocytic OAP across the cell surface is influenced by the existence of a basal lamina and neuronal activity, and that astrocytes possess a more remarkable plasticity of membrane structure than previously suspected.
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    URL: http://dx.doi.org/10.1007/BF00300229
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  • 35
    Electronic Resource
    Electronic Resource
    Fine structure and lectin histochemistry of the apical surface of the free neuromast of Lampetra japonica (1994)
    Springer
    Cell & tissue research 276 (1994), S. 245-252 
    Details
    ISSN: 1432-0878
    Keywords: Neuromast ; Hair cells ; Surface coat ; Electron microscopy ; Lectin histochemistry ; Lampetra japonica (Cyclostomata)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract The surface coat, ciliary process, and microvilli of the lamprey neuromast were examined with electron microscopy after tannic acid prefixation and lectin histochemistry. The neuromast was found to exist in the form of a dermal mound with a furrow in the middle. On the bottom of the furrow, the hair cell was characterized by a kinocilium and 15–20 stereocilia, arranged along the longitudinal axis of the furrow. Spanning structures were demonstrated between the kinocilium and stereocilia as well as between stereocilia. The surface coat, enhanced by tannic acid prefixation, was particularly rich over the surface of the supporting cell; by contrast, it was thin over the hair cell. Some lectins (PNA, GS-I, SBA, WGA) showed affinity to the surface coat of the supporting cell as well as the hair cell, and the others (RCA-I, MPA, ConA) showed affinity only to the supporting cell. These differences in the structure and affinities of the surface coat suggest an extracellular milieu highly specialized for the hair cell in this particular form of the mechanoreceptor.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00306110
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  • 36
    Electronic Resource
    Electronic Resource
    Zona glomerulosa of the adrenal gland in a transgenic strain of rat: a morphologic and functional study (1994)
    Springer
    Cell & tissue research 278 (1994), S. 21-28 
    Details
    ISSN: 1432-0878
    Keywords: Adrenal cortex ; Renin-angiotensin system ; Steroidogenesis ; Electron microscopy ; Morphometry ; Rat, transgenic (mRen2) 27
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract Transgenic rats for the murine Ren-2 gene display high blood pressure, low circulating levels of angiotensin II, and high renin content in the adrenal glands. Moreover, transgenic rats possess and increased aldosterone secretion (maximal from 6 to 18 weeks of age), paralleling the development of hypertension. To investigate further the cytophysiology of the adrenal glands of this strain of rats, we performed a combined morphometric and functional study of the zona glomerulosa of 10-week-old female transgenic rats. Morphometry did not reveal notable differences between zona glomerulosa cells of transgenic and age- and sex-matched Sprague-Dawley rats, with the exception of a marked accumulation of lipid droplets, in which cholesterol and cholesterol esters are stored. The volume of the lipid-droplet compartment underwent a significant decrease when transgenic rats were previously injected with angiotensin II or ACTH. Dispersed zona glomerulosa cells of transgenic rats showed a significantly higher basal aldosterone secretion, but their response to angiotensin II and ACTH was similar to that of Sprague-Dawley animals. Angiotensin II-receptor number and affinity were not dissimilar in zona glomerulosa cells of transgenic and Sprague-Dawley rats. These data suggest that the sustained stimulation of the adrenal renin-angiotensin system in transgenic animals causes an increase in the accumulation in zona glomerulosa cells of cholesterol available for steroidogenesis, as indicated by the expanded volume of the lipid-droplet compartment and the elevated basal steroidogenesis. However, the basal hyperfunction of the zona glomerulosa in transgenic animals does not appear to be coupled with an enhanced responsivity to its main secretagogues, at least in terms of aldosterone secretion.
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    URL: http://dx.doi.org/10.1007/BF00305774
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  • 37
    Electronic Resource
    Electronic Resource
    Morphological studies by light and electron microscopy of pancreatic acinar cells under the effect of Tityus serrulatus venom (1994)
    Springer
    Cell & tissue research 278 (1994), S. 255-264 
    Details
    ISSN: 1432-0878
    Keywords: Key words: Scorpion venom ; Exocrine pancreas ; Secretagogue ; Electron microscopy ; Pancreatitis ; cis-Golgi aggregates
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract. We studied in vivo and in vitro morphological aspects of pancreatic acinar cells after treatment with Tityus serrulatus venom (TSV). After three hours in an in vitro system, positive secretagogue effects of the venom were identifiable both at the light-microscopic (LM) and the electron-microscopic (EM) levels. At 1 μg/ml TSV, maximal secretion (as measured in a concomitant radiolabeling dose-response experiment) of exocrine proteins at 58% was manifest as a discharge of most zymogen granules (ZG) and consequent appearance of secretory material in acinar lumina. At the supramaximal dose of 10 μg/ml TSV, exocytotic images were often observed also with secretory contents previously discharged. The lowest dose of venom at 0.01 μg/ml caused no stimulation of zymogen discharge above resting secretion levels; however, morphological changes were observed. At high doses of TSV, both in vivo and in vitro, large aggregates associated with the cis-Golgi develop between this region and the endoplasmic reticulum (ER). Since Tityus venoms have been associated with causation of pancreatitis, we were interested in comparisons of our experimental tissue with parameters attributed to development of the disease. Our studies have demonstrated considerable evidence that large intracellular vacuoles, discharged ZG, effaced acinar lumina with disappearance of microvilli and other manifestations of possible early events in pancreatitis are indeed frequently observed both in pancreatic lobules in vitro and in whole pancreas in vivo when exposed to TSV.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00414168
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  • 38
    Electronic Resource
    Electronic Resource
    Zona glomerulosa of the adrenal gland in a transgenic strain of rat: a morphologic and functional study (1994)
    Springer
    Cell & tissue research 278 (1994), S. 21-28 
    Details
    ISSN: 1432-0878
    Keywords: Key words: Adrenal cortex ; Renin-angiotensin system ; Steroidogenesis ; Electron microscopy ; Morphometry ; Rat ; transgenic (mRen2) 27
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract. Transgenic rats for the murine Ren-2 gene display high blood pressure, low circulating levels of angiotensin II, and high renin content in the adrenal glands. Moreover, transgenic rats possess an increased aldosterone secretion (maximal from 6 to 18 weeks of age), paralleling the development of hypertension. To investigate further the cytophysiology of the adrenal glands of this strain of rats, we performed a combined morphometric and functional study of the zona glomerulosa of 10-week-old female transgenic rats. Morphometry did not reveal notable differences between zona glomerulosa cells of transgenic and age- and sex-matched Sprague-Dawley rats, with the exception of a marked accumulation of lipid droplets, in which cholesterol and cholesterol esters are stored. The volume of the lipid-droplet compartment underwent a significant decrease when transgenic rats were previously injected with angiotensin II or ACTH. Dispersed zona glomerulosa cells of transgenic rats showed a significantly higher basal aldosterone secretion, but their response to angiotensin II and ACTH was similar to that of Sprague-Dawley animals. Angiotensin II-receptor number and affinity were not dissimilar in zona glomerulosa cells of transgenic and Sprague-Dawley rats. These data suggest that the sustained stimulation of the adrenal renin-angiotensin system in transgenic animals causes an increase in the accumulation in zona glomerulosa cells of cholesterol available for steroidogenesis, as indicated by the expanded volume of the lipid-droplet compartment and the elevated basal steroidogenesis. However, the basal hyperfunction of the zona glomerulosa in transgenic animals does not appear to be coupled with an enhanced responsivity to its main secretagogues, at least in terms of aldosterone secretion.
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    URL: http://dx.doi.org/10.1007/BF00305774
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  • 39
    Electronic Resource
    Electronic Resource
    Immunocytochemical localization of a growth-associated protein (GAP-43) in rat adrenal gland (1994)
    Springer
    Cell & tissue research 275 (1994), S. 555-566 
    Details
    ISSN: 1432-0878
    Keywords: Adrenal ; Autonomic nervous system ; Schwann cells ; Tyrosine hydroxylase ; GAP-43 ; Electron microscopy ; Immunohistochemistry ; Rat (Wistar)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract We have localized at light and electron-microscopic level the growth-associated protein GAP-43 in adrenal gland using single and double labelling immunocytochemistry. Clusters of GAP-43-immunofluorescent chromaffin cells and many immunofluorescent fibres were observed in the medulla. GAP-43-immunoreactive fibres also formed a plexus under the capsule, crossed the cortex and ramified in the zona reticulata. Double labelled sections showed the coexpression of GAP-43 with a subpopulation of tyrosine hydroxylase-and of dopamine-β-hydroxylase-immunoreactive chromaffin cells. Dual colour immunofluorescence for GAP-43 and calcitonin gene-related peptide (CGRP) revealed that some of the GAP-43-immunoreactive fibres also express CGRP. Pre-embedding electron microscopy showed GAP-43 immunoreactivity associated with the plasma membranes and cytoplasm of noradrenaline-producing chromaffin cells, and with processes of nonmyelin-forming Schwann cells. Immunoreactive unmyelinated axons and terminals were also observed. The immunostained terminals made symmetrical synaptic contacts with chromaffin cells. Immunoreactive unmyelinated fibres and small terminals were present in the cortex. Our results show that GAP-43 is expressed in noradrenergic chromaffin cells and in various types of nerve fibres that innervate the adrenal. Likely origins for these fibres include preganglionic sympathetic fibres which innervate chromaffin cells, postganglionic sympathetic fibres in the cortex, and CGRP containing sensory fibres.
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    URL: http://dx.doi.org/10.1007/BF00318824
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  • 40
    Electronic Resource
    Electronic Resource
    Light- and electron-microscopic study of electrophysiologically characterized neurons in the mediolateral part of the lateral septum of the guinea-pig (1994)
    Springer
    Cell & tissue research 275 (1994), S. 543-553 
    Details
    ISSN: 1432-0878
    Keywords: Lateral septum ; Intracellular injections ; Electron microscopy ; Somatie spines ; Guinea-pig
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract In slices of guinea-pig brains, 36 neurons located in the mediolateral part of the lateral septum were stained intracellularly with horseradish peroxidase (n=28) or biocytin (n=8) after electrophysiological characterization. These neurons belonged to class A neurons (n=23), which generated pronounced Ca++-dependent high-threshold spikes in control medium, or to class C neurons (n=9), which were recognized by the occurrence of small-amplitude sodic spikes followed by slower larger calcic spikes. The present results demonstrate that, despite the variety of individual cell types, the major morphological population (30/36 cells) was composed of a homogeneous class of large-sized neurons that displayed thick primary dendrites and abundant dendritic appendages. The remaining 6 cells were small-sized, poorly-spiny neurons. Somatic spines were observed on 5 out of the 30 large cells and on one out of the six smaller cells. Labeled axons were mainly oriented to the anterior commissure. The axons of nine cells richly collateralized near the perikaryon. Ultrastructural examination of 3 horseradish peroxidase-injected cells showed indented nuclei, classic organelles and somatic spines. Terminal boutons established symmetric synapses with the injected cells. These results describe the morphological features of electrophysiologically identified neurons and indicate that class A and class C neurons are distributed among morphological populations differing in perikaryal size. This suggests that the different electrical properties of class A and class C neurons reflect recordings from different parts of the neuron rather than from neurons of different types. Furthermore, the present findings demonstrate that, in the guinea-pig, electrical and morphological characteristics of somatospiny neurons are comparable with those of non-somatospiny neurons. Somatospiny neurons have a recognized integrative role in the hippocampo-septo-hypothalamic complex.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00318823
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  • 41
    Electronic Resource
    Electronic Resource
    Quantitative analysis of rod-cored vesicles and dense granules of large granular lymphocytes in the liver, spleen, and peripheral blood of rats (1994)
    Springer
    Cell & tissue research 276 (1994), S. 187-195 
    Details
    ISSN: 1432-0878
    Keywords: Rod-coredvesicles ; Granules ; Lymphocytes ; Liver ; Electron microscopy ; Rat (Fischer F344/NCR)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract Large granular lymphocytes (LGL) comprise a natural defense system in the liver and exert an inhibitory effect on tumor cell metastasis. In order to demonstrate the maturation of LGL in the liver from the morphological aspect, we evaluated electron-microscopically the frequency of 0.2 μm vesicles (rod-cored and “empty” vesicles) and dense granules in LGL from the liver, spleen, and peripheral blood of the rat. Both of these cell organelles are characteristic to LGL and may relate to natural killer-mediated cytolysis. On the average, there were 12.7 of the 0.2 μm vesicles and 4.3 rod-cored vesicles (RCV) per cell section in the liver, 6.6 0.2 μm vesicles and 1.6 RCV in the spleen, and 8.6 0.2 μm vesicles and 0.9 RCV in the peripheral blood. The number of 0.2 μm vesicles per cell section ranged from 0 to 19 with the exception of a few higher instances. Therefore, LGL were divided into vesicle-rich(〉9 0.2 μm vesicles per cell section) and vesicle-poor (〈8 per cell section) populations. Hepatic LGL consisted mainly of a vesicle-rich population while splenic LGL consisted mainly of a vesicle-poor population, and peripheral blood contained equal proportions of both populations. In addition to diversity with regard to the number of 0.2 μm vesicles, LGL obtained from various organs also displayed heterogeneity in the number and size of dense granules. Since the number of dense granules per cell section usually ranged from 1 to 13, LGL were diveded into 2 populations, i.e., LGL with many (〉7 per cell section) granules and those with a few(〈6 per cell section) granules. Specifically, splenic LGL had a few small (average diameter, less than 400 nm) dense granules, while sections of LGL from the liver and peripheral blood displayed many small dense granules and a few large (〉400 nm) ones, respectively, in addition to the populations seen in the spleen. Thus, the present study has demonstrateda difference in the distribution of 0.2 μm vesicles in LGL based on the tissue of origin. The present study has revealed the difference in the distribution of 0.2 μm vesicles of LGL by tissue and indicated that immature LGL are predominant in the spleen, while hepatic LGL are generally more mature as defined by the number of vesicles. These data suggest that the microenvironment of the liver may contribute to the increased expression of these vesicles in LGL.
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    URL: http://dx.doi.org/10.1007/BF00354799
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  • 42
    Electronic Resource
    Electronic Resource
    Localization of GABAA receptors in the rabbit retina (1994)
    Springer
    Cell & tissue research 276 (1994), S. 295-307 
    Details
    ISSN: 1432-0878
    Keywords: GABAA receptors ; Light microscopy ; Electron microscopy ; α1 subunit ; β2/3 subunit ; γ2 subunit ; Immunocytochemistry ; Rabbit (New Zealand)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract The distribution of gamma-aminobutyric acidA (GABAA) receptors in the rabbit retina is investigated and compared with the distribution of GABAergic neurons using immunocytochemical methods. Antibodies against the α1, β2/3, and γ2 subunits of the GABAA receptor label subpopulations of bipolar, amacrine and ganglion cells. Double labeling experiments show that the γ2 subunit is colocalized with the α1 and the β2/3 subunits in bipolar, amacrine and ganglion cells. Electron microscopy reveals that in the outer plexiform layer, GABAA receptor immunoreactivity is present on dendrites of cone bipolar cells adjacent to the cone pedicles. Bipolar cell dendrites are also receptor-positive at synapses from interplexiform cells. Some receptor immunoreactivity is found intracellularly in processes of horizontal cells. In the inner plexiform layer, GABAA receptor immunoreactivity is present on both rod bipolar and cone bipolar axon terminals at putative GABAergic input sites. Amacrine and ganglion cell processes in sublamina a and b are also labeled.
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    URL: http://dx.doi.org/10.1007/BF00306115
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  • 43
    Electronic Resource
    Electronic Resource
    Negatively-stained polysomes on rough microsome vesicles viewed by electron microscopy: further evidence regarding the orientation of attached ribosomes (1994)
    Springer
    Cell & tissue research 276 (1994), S. 439-444 
    Details
    ISSN: 1432-0878
    Keywords: Polysomes ; Ribosomes ; Subunits ; Liver ; Electron microscopy ; Negative stain ; Rat (Sprague-Dawley)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract Rough microsomes, derived from rough endoplasmic reticulum of rat liver, were studied by electron microscopy after negative staining, to seek further information about the orientation of ribosomal small and large subunits in bound polysomes. Rough microsomal vesicles were fixed with 2% formaldehyde, centrifuged onto electron-microscopic grid membranes, and were then negatively-stained with 2% phosphotungstic acid. In these preparations, viewed with the electron microscope, flattened rough microsomal vesicles with bound polysomes were sometimes discernible, and the individual ribosomes in the polysomes occasionally showed small and large subunits. The small subunits were uniformly oriented toward the inside of the polysomal curve. The large and small subunits appeared to be alongside one another on the membrane, consistent with the orientation that has been described by Unwin and his co-workers. The boundary between the small and large subunits occurred at approximately the same level in the ribosome where inter-ribosomal strands have been described previously in surface views of bound polysomes in positively-stained electron-microscopic tissue sections. This further confirms the identity of the strands as messenger RNA.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00343942
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  • 44
    Electronic Resource
    Electronic Resource
    Morphological studies by light and electron microscopy of pancreatic acinar cells under the effect of Tityus serrulatus venom (1994)
    Springer
    Cell & tissue research 278 (1994), S. 255-264 
    Details
    ISSN: 1432-0878
    Keywords: Scorpion venom ; Exocrine pancreas ; Secretagogue ; Electron microscopy ; Pancreatitis ; cis-Golgi aggregates
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract We studied in vivo and in vitro morphological aspects of pancreatic acinar cells after treatment with Tityus serrulatus venom (TSV). After three hours in an in vitro system, positive secretagogue effects of the venom were identifiable both at the light-microscopic (LM) and the electron-microscopic (EM) levels. At 1 μg/ml TSV, maximal secretion (as measured in a concomitant radiolabeling dose-response experiment) of exocrine proteins at 58% was manifest as a discharge of most zymogen granules (ZG) and consequent appearance of secretory material in acinar lumina. At the supramaximal dose of 10 μg/ml TSV, exocytotic images were often observed also with secretory contents previously discharged. The lowest dose of venom at 0.01 μg/ml caused no stimulation of zymogen discharge above resting secretion levels; however, morphological changes were observed. At high doses of TSV, both in vivo and in vitro, large aggregates associated with the cis-Golgi develop between this region and the endoplasmic reticulum (ER). Since Tityus venoms have been associated with causation of pancreatitis, we were interested in comparisons of our experimental tissue with parameters attributed to development of the disease. Our studies have demonstrated considerable evidence that large intracellular vacuoles, discharged ZG, effaced acinar lumina with disappearance of microvilli and other manifestations of possible early events in pancreatitis are indeed frequently observed both in pancreatic lobules in vitro and in whole pancreas in vivo when exposed to TSV.
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  • 45
    Electronic Resource
    Electronic Resource
    Induction and formation ofCochliobolus sativus appressoria (1994)
    Springer
    Protoplasma 178 (1994), S. 34-47 
    Details
    ISSN: 1615-6102
    Keywords: Appressorium ; Cochliobolus sativus ; Electron microscopy ; Thigmotropism ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary GerminatingCochliobolus sativus spores were induced to form appressoria on a variety of artificial surfaces, including replicas of the barley leaf surface. Evidence was obtained for the involvement of chemical and topographic signals during induction of appressorium formation inC. sativus. Germ tube thigmotropism was also observed in vitro. Ultrastructure relevant to appressorium formation was observed, including the germ tube apex, apical swelling of the germ tube apex prior to appressorium formation, the appressorium with associated septation and the penetration peg. Cytochemical probes applied to germlings at the electron microscope level failed to detect α-D-mannan, α-D-glucan, β-D-galactan, D-glcNAc or D-galNAc polymers in the extracellular mucilage associated with the fungal germlings. The ultrastructure of hyphal apices from germlings grown under different nutritional conditions differed with respect to Spitzenkörper morphology, apex shape and in the quantity of associated extracellular mucilage. Experimental findings are discussed relative to current understanding of appressorium induction in more extensively studied systems.
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    URL: http://dx.doi.org/10.1007/BF01404119
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  • 46
    Electronic Resource
    Electronic Resource
    Morphology of sweat glands in determining time of death (1994)
    Springer
    International journal of legal medicine 107 (1994), S. 132-140 
    Details
    ISSN: 1437-1596
    Keywords: Time of death ; Sweat glands ; Immunohistochemistry ; Electron microscopy ; Todeszeit ; Schweißdrüsen Immunhistochemie ; Elektronenmikroskopie
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine , Law
    Description / Table of Contents: Zusammenfassung Diese Untersuchung zeigt postmortale autolytische Veränderungen in der Haut auf zellulärer und subzellulärer Ebene und identifiziert Parameter, welche helfen können, die Zeit des Todes in den ersten Stunden postmortem zu bestimmen. Hautproben von der Beugeseite des Arms wurden, 3, 6, 9 und 12. Stunden nach dem Tode von insgesamt 29 Leichen entnommen (verschiedene Altersklassen, keine Zeichen für Hauterkrankungen, verschiedene Todesursachen). Drei Arten der Untersuchungen wurden durchgeführt: zytochemisch (Hematoxylin-Eosin and Alcian-PAS), immunhistochemisch (S-100, CEA, Cytokeratin, ASM) und ultrastrukturell (Elektronenmikroskopie). Die Elektronenmikroskopie erwies sich als nützlich für die Identifizierung von Transformationen die für jeden chronologischen Schritt spezifisch waren: Reduktion des intrazellulären Glykogens in hellen Zellen und Reduktion der sekretorischen Granula in dunklen Zellen sind typische Zeichen für die erste Phase (3 Stunden) nach dem Tode; mitochondriale Dilatation und Rarifizierung der Cristae in hellen und dunklen Zellen sind typisch für die 2. Phase (6 Stunden); Rarifizierung der Microvilli in dunklen und hellen Zellen sind typisch für die 3. Phase (9 Stunden) und Kernpyknose von dunklen und hellen Zellen ist ein Zeichen der letzten Phase (12 Stunden). Zytochemie und Immunhistochemie sorgen für eine nützliche Information — dies gilt nicht für alle chronologischen Stadien, welche hier einbezogen wurden, aber für individuelle Phasen (3 Stunden für Hematoxylin-Eosin und 6 Stunden für Alcian-PAS). Es ist jedoch besonders wichtig, die Resultate von allen solchen Techniken simultan einzubeziehen, so daß die Frage der exakten Todeszeit innerhalb der ersten 12 Stunden postmortem genauer beantwortet werden kann.
    Notes: Abstract This study demonstrates post-mortem autolytic alterations in the skin at cellular and subcellular levels and identifies parameters which may assist in determining the time of death in the first few hours post-mortem. Serial skin samples from the ventral surface of the arm were taken at intervals of 3, 6, 9 and 12 h after death in 29 subjects of various ages, with no signs of skin disease; causes of death were various. Three types of tests were performed: cytochemical (hematoxylin-eosin and alcian-PAS), immunohistochemical (S-100, CEA, Cytokeratin, ASM) and ultrastructural (electron microscopy). Electron microscopy proved useful for identifying transformations which were found to be specific for each chronological step considered: reduction of intracellular glycogen in clear cells and reduction of secretory granules in dark cells are typcial signs of the first stage (3 h) after death; mitochondrial dilatation and rarefaction of cristae in clear and dark cells are typical of the second stage (6 h); rarefaction of microvilli in dark and clear cells is a sign of the last stage (12 h). Cytochemistry and immunohistochemistry supply useful information — not for all the chronological stage considered here, but for individual phases (3 h for hematoxylin-eosin and 6 h for alcian-PAS). However, it is particularly important to use the results from all such techniques simultaneously, so that the question of the exact time of death within the first 12 h post-mortem may be more accurately answered.
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    URL: http://dx.doi.org/10.1007/BF01225600
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  • 47
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    Electronic Resource
    Slowly progressive changes of the retina and retinal pigment epithelium in briard dogs with hereditary retinal dystrophy (1994)
    Springer
    Documenta ophthalmologica 87 (1994), S. 337-354 
    Details
    ISSN: 1573-2622
    Keywords: Animal model ; Briard dogs ; Electron microscopy ; Photoreceptors ; Retinal degeneration ; Retinal pigment epithelium
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Seven eyes from 2 generations of Briard dogs (5 weeks — 7 years old) with congenital night blindness and (in the second generation) impairment of day vision to varying degrees, were examined by light and electron microscopy. Specimens from 4 locations were studied: the central area, the midperiphery of the tapetal area, the upper periphery and the lower periphery. Disorientation of rod outer segment disc membranes was seen in the 5-week-old dog. Large electron-lucent inclusions were found in the RPE at 3.5 months of age. These inclusions occurred most frequently in the central and midperipheral-tapetal areas and seemed to increase in numbers and spread towards the periphery with increasing age. The content of these inclusions is not elucidated. Rod photoreceptor degeneration was apparent from 7 months of age and was most prominent in the peripheral areas. The cones were better preserved. The 7-year-old dog showed reduction of photoreceptors in the central and midperipheral-tapetal areas and almost complete photoreceptor degeneration in the periphery. This dog also showed severe changes of the inner retina in the peripheral fundus. It appears that these Briard dogs suffer from a very slowly progressive retinal degeneration, in which the photoreceptor degenerative changes do not correlate anatomically to the changes in the RPE cells. The disease seems to be different from the retinopathy described in the English Briards. It is not clear yet whether the lipid type of retinopathy found in American Briards is identical to the present disease.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01203343
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    UV-B and early cortical and nuclear changes in the human lens (1994)
    Springer
    Documenta ophthalmologica 88 (1994), S. 255-261 
    Details
    ISSN: 1573-2622
    Keywords: UV-irradiation ; Human lens ; Ageing ; Defense mechanisms ; Biomicroscopy ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Experimental studies in mice and rats have shown that UV (B) irradiation leads to specific lens changes, viz. yellowing of the nucleus and a multilayered epithelium in the anterior pole with disrupted cortical fibres underneath. Biomicroscopic and ultrastructural studies on ageing human lenses revealed yellowing of the lens nucleus and locally ruptured membranes and small opcities in the equatorial cortex. No changes in the anterior pole were ever observed. This discrepancy between the human and animal lens, contraindicating UV as an important risk factor for human cataract, is discussed and may be due to several factors: (1) a difference between the high level acute and low level chronic irradiation; (2) species differences: nocturnal animals may be unable to cope with bright light exposure; (3) differences in scavenger and other defense mechanisms between humans and animals.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01203679
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  • 49
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    Effects of aflatoxin B1 on in vitro cultures ofNicotiana tabacum var. Samsun (1994)
    Springer
    Mycopathologia 125 (1994), S. 93-105 
    Details
    ISSN: 1573-0832
    Keywords: Aflatoxin B1 ; Callus ; Differentiation ; Electron microscopy ; Organogenesis ; Tobacco
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract Calli ofNicotiana tabacum (tobacco) were treated with two dose ranges of aflatoxin B1 (0.1–2.0 µg ml−1 - low does; 5–25 µg ml−1 aflatoxin B1). The ability of calli to recover following 3 weeks of toxin exposure was also investigated. The I50 (50% inhibition) value for fresh mass accumulation was approximately 2 µg ml−1 AFB1. Fresh mass accumulation was significantly lower than the control value from 0.5 µg ml−1 AFB1. Following 3 weeks growth without a toxin source, the growth of calli up to and including 10 µg ml−1 AFB1, was significantly greater than control calli, indicating reversibility of the toxic effects. With increasing toxin concentration, chlorophyll content of callus was inhibited from 0.5 µg ml−1. Transfer to a toxin-free medium resulted in a degree of recovery (up to 0.5 µg ml−1). In the dose range 5–25 µg ml−1, the levels of chlorophyll were drastically reduced, with no recovery following AFB1 removal. Electron microscopy revealed a disruption of chloroplast structure as an early deteriorative event in AFB1 exposure of callus cells. Protein levels were less sensitive, with inhibition manifested only in the high dose range. Shoot development occurred at all concentrations, but was significantly inhibited from 5 µg ml−1 AFB1. Recovery following toxin removal was minimal at these higher AFB1 concentrations. The number of necrotic calli increased progressively from 5 µg ml−1 as toxin levels increased.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01371098
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  • 50
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    Electron microscopic and light scattering observation on a system with two iridescent phases (1994)
    Springer
    Colloid & polymer science 272 (1994), S. 604-611 
    Details
    ISSN: 1435-1536
    Keywords: Electron microscopy ; light scattering ; dodecyldimethylaminoxide/hexanol/water ; iridescent phase ; bicontinuous sponge phase ; vesicle phase
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics
    Notes: Abstract Electron microscopic observations and classical light-scattering measurements have been carried out for dodecyldimethylaminoxide/hexanol/water mixtures in the concentration range where iridescent colors occur. This system has two different iridescent phases. The iridescent phase with more hexanol forms quickly, and the phase with less hexanol forms very slowly. Three different isotropic phases which show strong flow birefringence are found near both iridescent phases. The electron microscopic pictures show clearly that only one of these isotropic phases with strong flow birefringence is a bicontinuous sponge phase (L3h -phase). This is the phase which comes out by adding some alkanol to the upper lamellar phase. The flow birefringent phase below the lower lamellar phase forms unilamellar vesicles. The flow birefringent phase which occurs between both iridescent phases contains multilamellar vesicles and is shown to be a precursor of a lamellar phase.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00653228
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  • 51
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    Ultrastructure of Reissner's membrane in the rabbit (1994)
    Springer
    European archives of oto-rhino-laryngology and head & neck 251 (1994), S. 249-256 
    Details
    ISSN: 1434-4726
    Keywords: Reissner's membrane ; Electron microscopy ; Tubulocisternal endoplasmic reticulum ; Subsurface cistern ; Rabbit
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The ultrastructure of Reissner's membrane in the rabbit is described following vascular perfusion-fixation of live, anesthetized and artificially respirated healthy animals. A new and improved technique of fixation is employed that includes a pressure feedback controlled peristaltic pump and an oxygen-carrying fixative. In ultrathin sections capillaries were observed between the two cell layers comprising Reissner's membrane. The mesothelial cells facing the scala vestibuli were connected by junctional complexes and neither pores nor discontinuities were observed in the cell layer. In the epithelial cells a well-developed tubulocisternal endoplasmic reticulum (TER) was noted. Computerized three-dimensional reconstruction documented the continuity of this TER, from prominent disc-shaped subsurface cisterns lining the luminal cell membrane to smaller subsurface cisterns lining the abluminal and lateral cell membranes, forming a transcellular canalicular pathway. The possible function of the TER in Reissner's membrane is discussed with reference to endolymph/perilymph homeostasis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00181879
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  • 52
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    Morphological changes in the tectorial and basilar membranes of aged rats (1994)
    Springer
    European archives of oto-rhino-laryngology and head & neck 251 (1994), S. 357-360 
    Details
    ISSN: 1434-4726
    Keywords: Presbycusis ; Extracelluar matrix ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Using both light and transmission electron microscopy presbycusic degeneration of the cochlea was observed in particular in the tectorial and basilar membranes, in naturally aged rats. These animals showed a descending auditory pattern as determined by auditory brainstem response. Ultrastructurally, the number of collagen fibers in the tectorial membrane was reduced and straight type A fibers were increased relative to branched, coiled type B fibers. The basilar membrane in the basal turn was also thickened by an increased homogeneous ground substance. These findings indicate that the specificity of vibration of the tectorial and basal membranes is very different in aged and young rats.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00171545
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  • 53
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    Nitrostyrene Derivatives of Adenosine 5′-Glutarates Modified with an Alkyl Spacer and their inhibitory activity on epidermal growth factor receptor protein tyrosine kinase (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 59-69 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: β-Nitrostyrene derivatives of adenosine 5′-glutarates are potent and selective bisubstrate-type inhibitors of the epidermal growth factor receptor protein tyrosine kinase (EGF-R PTK). In an attempt to improve the inhibitory activity, this type of compounds was modified with alkyl spacers of varying length between the nitrostyrene and the glutaryl units. The spacers consisted of 1, 3, 4, and 5 atoms to give compounds of the benzyl, oxyethyl, oxypropyl, and oxybutyl series, respectively (Schemes 1 and 2). Adenosine 5′-esters were prepared in the benzyl and oxypropyl series only. Compared to the compounds in the parent series without spacer (IC50 = 0.7-12 μM), most of the modified compounds inhibited the EGF-R PTK only marginally or were inactive (IC50 ≥ 100 μM). The only exceptions were the free acids 19 and 20 with IC50 values of ca. 5 μM. It is noteworthy that esterification of these two hydrogen glutarates with either MeOH or adenosine yielded inactive compounds, which is in contrast to the corresponding substances without spacers.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19940770109
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    Synthese und Eigenschaften der Furo- und Thieno-Analogen von PQQ-TriesterTeil einer Präsentation am ‘2nd International Symposium on PQQ and Quinoproteins’, 19.-22. Nov. 1991, Yamaguchi, Japan. (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 100-110 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis and Characterization of the Furo and Thieno Analogues of the Triester of PQQWe report here the synthesis and properties of the furo and thieno analogues of 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9- tricarboxylic acid ( = PQQ), i.e. the furo- and thieno[2,3-f]quinoline-4,5-quinone (FQQ and TQQ, resp.) derivatives B and C, obtained as triesters. The triester of PQQ derivative A is much more stable than the triesters of B or C, and only the triester of A shows strong activity in nonenzymatic catalytic oxidations.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770113
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  • 55
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    Computational Approach to the Receptor-Bound Conformation of Cyclosporin A (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 171-181 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The conversion of the conformation of cyclosporin A (CsA) observed in CHCl3 to the receptor-bound state is investigated by two molecular-mechanics methods, template forcing and dynamic forcing. The conformations of CsA in CHCl3 and complexed with LiCl in THF as determined by NMR are used as starting structures. The transition starting from the CsA/CHCl3-derived conformation is hindered by steric interactions of two side chains (MeBmt1 and Val5). While starting with the CsA/LiCl-derived conformation, the conversion is facile. It is illustrated that these calculations, which are of artificial character, using only the starting and final structures of the observed conformational transition during the receptor-binding event, allow an insight into the interactions between the substrates and receptor in terms of an induced fit.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770120
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  • 56
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    Electrochemical Study of Phase-Transfer Catalysis Reactions: The Williamson ether synthesis (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 231-242 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The transfer properties of the ionic species involved in the Williamson ether synthesis by phase-transfer catalysis were investigated using electrochemical techniques developed for the study of polarised liquid/liquid interfaces. This approach allows the measurement of the apparent partition coefficients of the transferring species. From these data, it is proposed that the role of the phase-transfer catalyst salt in the reaction mechanism is to establish a Galvani distribution potential difference between the two phases which in turn acts as the driving force for transferring the reactive aqueous ions to the organic phase.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770125
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  • 57
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    Synthesis of (R)- and (S)-5-(Hydroxymethyl)-3-isopropyloxazolidin-2-one, intermediates in the preparation of optically active β-blockers (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 252-256 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The (R)- and (S)-5-(hydroxymethyl)-3-isopropyloxazolidin-2-ones, ((R)- and (S)-2, resp.), pivotal intermediates in the preparation of optically active β-blockers, were synthesized using (R,E)-2-hydroxypent-3-enenitrile (1) as the chiral starting material. In the synthesis of (R)-2, a known cyclization/inversion step was applied.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770127
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  • 58
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    Calorimetric Measurements of the Complexation of Cyclosporin A, Ascomycin, Fujimycin, and Rapamycin with Lithium Chloride and with an Immunophilin (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 291-305 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Solutions (2 ml) of small linear and cyclic peptides (4-11), of a peptolide containing nine amino acids and a lactate moiety (12), of the cyclic undecapeptide cyclosporin A (CS, 1), and of the macrolides ascomycin, fujimycin, and rapamycin (13-15) in THF were added to excess LiCl, LiBr, or LiClO4 (up to 3000 equiv. in 40 ml THF) in a calorimeter (calorimetric titration). The enthalpies of interaction measured are in the range of ΔH = -8 to -37 kcal/mol. A similar experiment was carried out with one of the binding proteins of cyclosporin, the human cyclophilin A, to give the thermodynamic parameters for the complexation ΔH = -16, ΔG° = -10 kcal/mol, and ΔS° = -20 cal/mol·deg. at 25° which corresponds to an equilibrium constant K = 2·107 l/mol, in good agreement with the result of independent measurements using different methods. NMR Measurements of the macrolides in (D8)THF containing LiCl show strong down-field shifts of signals of the H-atoms next to C=O and C-OH groups in these molecules.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770129
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  • 59
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    NMR of Terminal Oxygen. Part 13Part 12: [1].. 17O-NMR spectra of C-nitroso compounds, thionitrites and NO+ Ion: Resonance effects in O=N - X compounds and correlation with CD spectra (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 306-316 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 17O-NMR signals of four true C-nitroso compounds 1-4 appear at particularly low field (1550-1265 ppm), whereas the dimers (azodioxy type) resonate at ca. 400 ppm and the ‘isonitroso compounds’ ( = quinone-oximes; 5 and 6) at ca. 250 ppm. S-Nitroso compounds ( = thionitrites; 8 and 9) show shift values of ca. 1300 ppm, not far from C - NO; the NO+ ion is much stronger shielded (474 ppm). The results, together with those for higher-shielded nitroso compounds X - NO (X = RO, R2N, Cl, O-) are discussed in terms of (a) resonance stabilization through n-donation from X(π-bond order, approximated by the known barriers of rotation around the X - N bond) and of (b) electronic excitation energies ΔE. The latter are approximated by long-wave (symmetry-forbidden) UV/VIS absorptions and confirmed, where available, by the maxima of the curves of circular dichroism (CD); the CD curve of thionitrite 9 has been measured. It is found that the δ(17O) values of X - NO depend both on bond order and on ΔE, which could not be separated. The higher shielding of NO+ compared with X - N=O is explained on the basis of anisotropy effects, which differ between sp and sp2 systems.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770130
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    Electronic Resource
    Masthead (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994) 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770101
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  • 61
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    Enantioselective synthesis of (-)-conduramine C1 and aminobromocyclitol derivatives‘Naked Sugars’ as Synthetic Intermediates, Part XXV. Part XXIV, see [1a]; Part XXIII, see [1b]. (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 1-9 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (1S,2R,6R,7R)-4-Phenyl-3,10-dioxa-5-azatricyclo[5.2.1.02,6]dec-4-en-9-one ((+)-5) obtained in 6 steps from the Diels-Alder adduct of furan to 1-cyanovinyl (1S)-camphanate ((+)-3) was reduced to the corresponding endo-alcohol (-)-6 the treatment of which with HBr/AcOH provided (-)-(3aS,4S,6R,7S,7aR)-4β-bromo-3aβ,4,5,6,7,7aβ-hexahydro-2-phenyl-1,3-benzoxazole-6β,7α-diyl diacetate ((-)-17). Elimination of HBr with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and acidic hydrolysis furnished (-)-(1R,2S,3R,4R)-4-aminocyclohex-5-ene-1,2,3-triol ( = (-)-conduramine C1;(-)-1).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770103
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    Nucleotides Part XLPart XXXIX: [1].. Synthesis and Characterization of Modified 2′-5′ Adenylate Trimers-Potential Antiviral Agents (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 10-22 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2′-5′ Adenylate trimers 41-44 carrying the (tert-butyl)dimethylsilyl (tbds) group at the 3′-OH position of various sugar moieties were synthesized via the phosphoramidite method. The use of the (tert-butyloxy)carbonyl (boc) and 2-(4-nitrophenyl)ethylsulfonyl (npes) groups for 2′-OH protection in neighbourhood to the 3′-O-tbds residue was compared during the synthesis of the target trimers. For other functional positions, the use of the 2-(4-nitrophenyl)ethyl (npe) and 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) blocking groups were favoured.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19940770104
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    Metal complexes of macrocyclic ligands. Part XXXVIIPart XXXVI: [1].. Synthesis of Heteroditopic Bis-macrocycles and Their Potential for Preparing Heterobinuclear Metal Complexes (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 23-35 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new and generally applicable synthetic path for the preparation of heteroditopic bis-macrocycles using tri-N-protected tetraazacycloalkanes as building blocks and bromoacetyl bromide as bridging reagent is described. In the first step, bromoacetyl bromide is used as acylating agent for one of the macrocycles, whereas in the second step it is used as alkylating agent for the second macrocycle, thus giving protected bis-macrocyclic amides (e.g. 6). After reduction of the amide moiety and deprotection, bis-azamacrocycles with an ethylene bridge are obtained (e.g. 8). The corresponding homoditopic bis-macrocycles 16 and 17 are also prepared for comparison purpose. Spectrophotometric studies indicate that bis-macrocycle 8, which consists of a 12- and a 14-membered ring, binds two metal ions with equal affinity, whereas compound 13, in which an unsubstituted (cyclam) and a trimethyl-substituted tetraazacyclotetradecane unit (Me3cyclam) are bridged, shows selective metal-ion binding. The first metal ion is always incorporated into the cyclam unit, whereas the second one binds to the Me3cyclam macrocycle. Thus, by sequential addition of two different metal ions, heterobinuclear complexes can easily be prepared. The electrochemistry of the binuclear Ni2+ complexes, studied by CV and DPV, as well as the EPR spectra of the binuclear Cu2+ complexes clearly indicate metal-metal interactions.
    Additional Material: 10 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19940770105
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    Thermoconversion of Caryophyllene- to Farnesene-Type Sesquiterpenes. Short access to the enantiomers of (6RS,7RS)- and (6RS,7SR)-6,7-epoxy-6,7-dihydro-β-farnesenes (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 36-40 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Flash-vacuum thermolysis of the four diastereoisomeric 5,6-epoxy-5,6-dihydro-caryophyllenes 1-4 at 500-550°/0.1-0.7 Torr leads to the hitherto unreported enantiomers of (6RS,7RS)- and (6RS,7SR)-6,7-epoxy-6,7-dihydro-β-farnesenes ((±)-5 and (±)-6, resp.). In particular, (+)-5 is formed in 45% yield (ca. 90% ee) and is, thus, an attractive chiral building block for natural-product synthesis.
    Additional Material: 2 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19940770106
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  • 65
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    Oceanapins A-F, Unique Branched Ceramides Isolated from the Haplosclerid Sponge Oceanapia cf. tenuis of the Coral SeaDedicated to the memory of Margherita Ratti (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 51-58 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of ceramides, called oceanapins A-F (2-7), which are unique for branching at both the sphingosine and fatty-acid chains, have been isolated as pure compounds from the haplosclerid sponge Oceanapia cf. tenuis of the Coral Sea. Following acid hydrolysis, both the fatty-acid and the sphingosine portions were obtained separately, which allowed their unequivocal structural definition. The absolute configuration was secured via protection of C(1′)-OH and Mosher's esterification at C(3′)-OH of the oceanapins.
    Additional Material: 1 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19940770108
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    Single-Crystal Structure of the Solvent-Separated Radical Ion Pair [9,10-diphenylanthracene.⊖][Na⊕(THF)6] and its implication for cation solvationDedicated to Peter Weyerstahl on the occasion of his 60th birthdayPart 26 of ‘Structures of Charge-Perturbed or Sterically Overcrowded Molecules’; Part 25: [1]. (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 41-50 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The one-electron transfer to large π-delocalized hydrocarbons provides an interesting possibility to crystallize solvent-separated ion-pair salts containing optimally solvated cations. Accordingly, the reduction of 9,10-diphenylanthracene in aprotic THF solution at a sodium metal mirror allows to grow dark-blue prismatic crystals of its radical anion and sixfold THF-solvated sodium cation. The structure of the radical anion is very similar to that recently published for the neutral molecule. According to AM1 hypersurface calculations based on the structural data, the phenyl twist angles obviously must be determined by lattice packing, and the negative charge is delocalized predominantly within the anthracene π system. The counter cation [Na⊕(THF)6], reported ordered for the first time, shows nearly octahedral coordination within a rather densily packed solvent shell. Due to the strong repulsions between the solvent molecules, its isodesmically calculated solvation enthalpy is smaller than that of the analogous dimethoxyethane complex [Na⊕(DME)3].
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19940770107
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    Radical Cations of Tetrazinodi(heteroarenes): An ESR and ENDOR Study (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 86-91 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 14N- and 1H-Coupling constants, determined by ESR, ENDOR, and general-TRIPLE-resonance spectroscopy, are reported for the radical cations of tetrazinodi(heteroarenes) 1-8. The results comply with the expectation that donor properties of these compounds are mainly due to the electron-rich dihydrotetrazine ring.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19940770111
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  • 68
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    Antiparallel β-Sheet Conformation in Cyclopeptides Containing a Pseudo-amino Acid with a biphenyl moiety (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 70-85 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The biphenyl-containing pseudo-amino acids 2′-(aminomethyl)biphenyl-2-carboxylic acid (Abc; 1) and 2′-(aminomethyl)biphenyl-2-acetic acid (Aba; 2) are used as rigid spacers in the backbone of the cyclic peptides cyclo (-Abc-Ala-Phe-Gly-)2 (5), cyclo(-Abc-Ala-Val-Gly-)2 (6), cyclo(-Aba-Gly-Phe-Ala-)2 (7), and cyclo(-Aba-Ala-Phe-Gly-)2(8). Three different interconverting diastereoisomers are found in solutions of each of these cyclopeptides due to the atropisomerism of the biphenyl units. NMR Techniques and molecular-dynamics calculations allow to conclude that the major diastereoisomer of 5 (and 6) in (D6)DMSO adopts a β-sheet conformation. It is proposed that the pseudo-amino acid 1 of (R)-chirality forms, with attached L-amino acids, a H-bonding pattern comparable to a β-turn (see D in Fig. 4 and F).
    Additional Material: 8 Ill.
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  • 69
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    Vitamin-B12-katalysierte C,C-Bindungsverknüpfung: Synthese von Jasmonaten via sequentielle Radikal-Reaktion (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 92-99 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Vitamin-B12-Catalyzed C, C-Bond Formation: Synthesis of Jasmonates via Sequential Radical ReactionThe Cbl-catalyzed electroreduction of 3-(2′-bromo-1′-ethoxyethoxy)cyclopenten (1a) in presence of 1-cyanovinyl-acetate (8) gave, in a sequential radical reaction (5-exo-trig-cyclization of 1a followed by addition to 8), 1-cyano-2-(2′-ethoxy-hexahydro-2′H-cyclopenta[b] furan-4′-yl)ethyl acetate (10a). This intermediate was transformed to methyl jasmonate (7; four steps) and epituberolide (9; three steps) in 20 and 31% yield, respectively, from cyclopent-2-en-l-ol.
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    URL: http://dx.doi.org/10.1002/hlca.19940770112
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  • 70
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    Die Synthese von Azaisomeren des Triesters von PQQ: 3H-Pyrrolo[3,2-f]-, 1H-Pyrrolo[3,2-h]- und 7H-Pyrrolo[2,3-h]chinolinchinon-Derivate (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 111-120 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Synthesis of Azaisomers of the Triester of PQQ: 3H-Pyrrolo[3,2-f]-, 1H-Pyrrolo[3,2-h]-, and 7H-Pyrrolo[2,3-h]quinolinequinone DerivativesWe describe here the synthesis of the title compounds 3-5, starting from highly substituted aminoindoles. The annelated pyridine rings were built up in each case with dimethyl 4-oxoglutaconate according to Corey's procedure. All three o-quinone derivatives 3-5 are stable compounds, comparable to PQQ-triester. The azaisomers vary in biological activity from practically inactive to strong inhibition of the α-amidating enzyme or the ornithin decarboxylase.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770114
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  • 71
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    A Novel Approach to 2,2-Disubstituted 1,2-Dihydro-4-phenylquinolines (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 608-614 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of 2-(1-phenylvinyl)aniline and 4-chloro-2-(1-phenylvinyl)aniline with acetophenone derivatives, 1-(naphthalen-1-yl)ethanone and 1-(furan-2-yl)ethanone in toluene at 110-115° with toluene-4-sulfonic acid as a catalyst leads in good-to-excellent yields to the 2,2-disubstituted 1,2-dihydro-4-phenyl-quinolines 1-18 (Scheme 1, Table). The structure of the new racemic 1,2-dihydroquinolines 1-18 is determined by NMR spectroscopy. A reaction mechanism proceeding via a 6π-electrocyclic rearrangement of 2-(1-phenylvinyl)anils 19 as the key step is proposed for the formation of these compounds (Scheme 1). The scope and limitations of the novel methods are discussed (Scheme 2).
    Additional Material: 1 Tab.
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  • 72
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    Facile Synthesis of 2′-Deoxyisoguanosine and Related 2′,3′-Dideoxyribonucleosides (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 622-630 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 2′-deoxyisoguanosine (1) was synthesized by a two-step procedure from 2′-deoxyguanosine (5). Amination of silylated 2′-deoxyguanosine yielded 2-amino-2′-deoxyadenosine (6) which was subjected to selective deamination of the 2-NH2 group resulting in compound 1. Also 2′,3′-dideoxyisoguanosine (2) was prepared employing the photo-substitution of the 2-substituent of 2-chloro-2′,3′-dideoxyadenosine (4). The latter was synthesized by Barton deoxygenation from 2-chloro-2′-deoxyadenosine (3) or via glycosylation of 2,6-dichloropurine (12) with the lactol 13. Compound 1 was less stable at the N-glycosylic bond than 2′-deoxyguanosine (5). The dideoxynucleoside 2 was deaminated by adenosine deaminase affording 2′,3′-dideoxyxanthosine (17).
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19940770305
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  • 73
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    Derivatives of (2R)-N-Glyoxylbornane-10,2-sultam and Their Use as auxiliaries in the diastereoselective spirocyclization of 2-substituted tryptamines7th Communication on ‘Indoles, Indolenines, and Indolines’; 6th communication: [1]. (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 615-621 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A crude hydrate 6 and a crystalline hemiacetal 7 of glyoxylamide 4 were prepared from crotonamide 5 (Scheme 2). Particularly hemiacetal 7, but also 6 and the ‘dimer’ 8 (obtained from 7) may serve as homochiral auxiliaries. The structure of 8 was determined by X-ray analysis. By arenesulfonyl halides, tryptimines 12-14 of 4 were diastereoselectively transformed into spirotricycles 15-17 and 19.
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    URL: http://dx.doi.org/10.1002/hlca.19940770304
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  • 74
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    Synthesis and Conformational Analysis of 2′-Deoxy-2′-(3-methoxybenzamido)adenosine, a rational-designed inhibitor of trypanosomal glyceraldehyde phosphate dehydrogenase (GAPDH) (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 631-644 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of 2′-benzamido-2′-deoxyadenosine analogues were synthesized in an effort to find new lead structures for the treatment of sleeping sickness. The 2′-deoxy-2′-(3-methoxybenzamido)adenosine (1h) was proved to be a selective inhibitor of the parasite glyceraldehyde 3-phosphate dehydrogenase which confirms the modeling studies. The solution-state conformation of 2′-(thiophene-2-carboxamido) analogue 1d demonstrates a 2′-endo conformation, an orientation of the thiophene ring under the ribose moiety, and the base part occupying a ‘syn’/‘anti’ equilibrium.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19940770306
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  • 75
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    Enantioselective Formation of Bicyclic Lactones by Rhodium-Catalyzed Intramolecular CH-insertion reactions (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 645-654 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The decomposition of cyclohexyl diazoacetate (5a) in the presence of the chiral [Rh2{(2S)-mepy}4] catalyst leads to a 3:1 cis/trans mixture of bicyclic lactone 6a with an enantiomeric excess of 95-97% (cis) and 90% (trans). The conformationally rigid tert-butyl derivatives 5b and 5c afford, in the presence of the same catalyst, 6b and 6c, respectively, via insertion into the equatorial C—H bonds exclusively, with ee's of ca. 95%. A remarkable degree of induction (92-95%) results in the lactone 6g upon decomposition of 1-isopropyl-2-methylpropyl diazoacetate (5g). The diazoacetates derived from 1-methylcyclohexanol, cyclopentanol and 1-methylcyclopentanol (5d-f) afford under similar conditions insertion products with higher diastereoselectivity, but significantly lower enantioselectivity. Other dirhodium catalysts are less efficient.
    Additional Material: 2 Tab.
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  • 76
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    A Concise Synthesis of (E)- and (Z)-Neomanoalides (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 661-667 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The first synthesis of (Z)-neomanoalide (4) and an improved synthesis of its (E)-isomer 3 was accomplished in a concise, regiocontrolled manner by exploiting 2-[(tert-butyl)dimethylsiloxy]-4{[(tert-butyl)dimethylsiloxy]-methyl}furan (6) as the key reagent. Lithiation of 6 and subsequent reaction with the (2Z)- or (2E)-isomer of (6E)-3-{[(tert-butyl)dimethylsiloxy]methyl}-7-methyl-9-(2′,6′,6′-trimethylcyclohex-1′-enyl)nona-2,6-dienyl bromide (5), followed by hydrolysis, afforded the corresponding neomanoalide.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770309
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  • 77
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    Stable Quinone Methides: Regioselective para-Oxidation of a 2,4-bis[(alkylthio)methyl]phenol and addition reactions to quinonemethides (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 655-660 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 2,4-bis-functionalized phenol 1 is dehydrogenated regioselectivity with potassium ferricyanide, affording the corresponding p-quinonemethide 2. Hydrolysis of 2 affords a mixture of dithioacetal 5a and benzaldehyde 6; 1,6-addition of thiols to 2 gives the dithioacetals 5 of benzaldehyde 6; reaction of 2 with 2,2′-azobis(isobutyronitrile) (= 2,2′-dimethyl-2,2′-azobis(propanenitrile)) leads to 9a, 9b, and 10, addition products of the 1-cyano-1-methylethyl radical. The structures of all products are confirmed mainly by 1H- and 13C-NMR spectroscopy, and the mode of their formation is discussed.
    Additional Material: 2 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19940770308
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  • 78
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    Oligosaccharides Related to Tumor-Associate Antigens. Part 2Part 1: [1].. Conformational analysis of the trisaccharide α-L-Fucp-(1→2)-β-D-Galp-(1→3)-β-D-GalpNAc, epitope structure recognized by the MBr1 antibody (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 668-678 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The conformational space of the trisaccharide α-L-Fuc-(1→2)-β- D-Gal-(1→3)-β -D-GalNAc-1-OPr (2) and of its component disaccharide moieties α -L-Fuc-(1→2)-β -D-Gal-1-OMe (3) and β -D-Gal-(1→3)-β- D-GalNAc-1-OPr (4) was investigated with the aid of molecular-mechanics energy minimizations and molecular-dynamics simulations. These calculations suggested the occurrence of two conformations for each compound characterized by different φ and Ψ glycosidic angles. However, 1H-NMR investigation of D2O solutions of 2-4 indicated a sure preference for one of the two conformers with a contribution of the other one ranging from negligible to low.
    Additional Material: 7 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19940770310
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  • 79
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    Synthesis of a New Bivalent Hirudin Analog (hirufos), which includes a stable 4′-phosphono-L-phenylalanine mimic of (L-tyrosine O4-sulfate)-63 (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 679-684 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis on solid phase of a new derivative of the anticoagulant protein hirudin is described (see Scheme and Fig.1, I). The henicosapeptide is a bivalent conjugate of the C-terminus of hirudin and of the active-site-binding tetrapeptide D-Phe-Pro-Arg-Pro linked via a tetraglycine spacer. The peptide, for which the name hirufos was coined, incorporates a stable phosphono derivative of L-phenylalanine which, combined with the other structural modifications, leads to a potent anticoagulant agent. Synthesis was readily achieved by the (9H-fluoren-9-yl)-methoxycarbonyl (Fmoc) strategy followed by acidolytic cleavage from the resin and deprotection, including the liberation of the crucial phosphonic group on L-phenylalanine.
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    URL: http://dx.doi.org/10.1002/hlca.19940770311
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  • 80
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    Organic Reactions in the Solid State: The reactivity of guest molecules in tri-o-thymotide clathrates (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 691-708 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Tri-o-thymotide (TOT) clathrates are enantiomorphous and enantioselective (chiral cages). It was shown that an external molecular reactant can diffuse into the TOT host crystal lattice and reacts with the included molecule (guest) in characteristic ways, differing from those occurring in liquid solutions. Several aspects of the action of hydrogen halides (HCl, HBr) on the chemical behavior of included oxiranes were investigated for solid-gas and solid-liquid (aqueous) systems. Under well established experimental conditions, these reactions gave regiospecifically one target product and were asymmetric. The included substrate underwent first an acid-catalyzed allylic isomerization that is cage-specific and mostly quantitative. In sheer contrast, strong basic conditions were required to promote, in reduced yield, the analogous transformation in solution. The regiospecificity and enantioselectivity of several intra-crystalline conversions allowed the accurate determination of the absolute configuration of several guest molecules. Kinetic measurements were achieved that disclosed some striking features of this new type of heterogeneous reactions. Tentative models for the cage stereoselective mechanisms are briefly discussed.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19940770313
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  • 81
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    1:1 Metal Complexes of Bivalent Cobalt, Nickel, Copper, Zink, and Cadmium with the Tripodal Ligand tris[2-(dimethylamino)ethyl]amine: Their stabilities and the X-ray crystal structure of its copper(II) complex sulfate (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 685-690 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The complex formation by Co2+, Ni2+, Cu2+, Zn2+, and Cd2+ with tris[2-(dimethylamino)ethyl]amine (N(CH2CH2NMe2)3, Me6tren) was investigated at 25° and at an ionic strength of 1, using VIS spectroscopy and potentiometric measurements. The stability constants of these complexes are compared with those of tris(2-aminoethyl)amine (N(CH2CH2NH2)3, tren), obtained under the same conditions. The values of the constants for Me6tren are much lower than those for tren, due to the bulky Me substituents. The values of the constants can be correlated with the ability of the individual metal ions to adopt coordination number 5. This appears to be easier for Cu2+ and Co2+ than for Cd2+ and Zn2+ and is very difficult for Ni2+. The 1:1 complexes [ML(H2O)]2+ are monoprotonic acids whose pKs values are similar or lower than those of the corresponding aquametal ions. The X-ray crystal structure of the copper(II) complex [Cu(SO4)(Me6tren)] · 8H2O reveals pentacoordination at the central ion. The UV/VIS spectra of the aqueous solutions of the Co2+, Ni2+, and Cu2+ 1:1 complexes confirm that the same coordination number is present also in these complexes.
    Additional Material: 5 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19940770312
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  • 82
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    The Revised Structure of the Norditerpenoid Alkaloid Peregrine (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 1768-1772 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The structure of peregrine (1), a norditerpenoid alkaloid isolated from Delphinium peregrinum var. elongatum BOISS., was revised on the basis of the 1H-COSY, HMQC, HMBC, and ROESY NMR spectra and of the X-ray analysis of its parent alcohol 2. Some of the 13C-NMR resonances of 1 and the related alkaloids peregrine alcohol (2), 14-O-acetylperegrine (3), bicoloridine (4), bicoloridine alcohol (5), 6-O-acetylbicolorine (6), bicolorine (7), and 14-O-acetylbicolorine (8), were also reassigned.
    Additional Material: 4 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19940770708
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  • 83
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    Nucleotides. Part XLIVPart XLIII: [1].. Synthesis, characterization, and biological activity of monomeric and trimeric cordycepin-cholesterol conjugates and inhibition of HIV-1 replication (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 1757-1767 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The antivirally active 3′-deoxyadenylyl-(2′-5′)-3′-deoxyadenylyl-(2′-5′)-3′-deoxyadenosine (cordycepin trimer core) was modified at the 2′- or 5′-terminus, by attachment of cholesterol via a carbonate bond (→ 15) or a succinate linker (→ 16 and 27) to improve cell permeability. The corresponding monomeric conjugates 4, 7, and 21 of cordycepin were prepared as model substances to study the applicability of the anticipated protecting groups - the monomethoxytrityl (MeOTr), the (tert-butyl)dimethylsilyl (tbds), and the β -eliminating 2-(4-nitrophenyl)ethyl (npe) and 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) groups - for the final deblocking steps without harming the ester bonds of the conjugate trimers. The syntheses were performed in solution using phosphoramidite chemistry. The fully protected trimer conjugates 13, 14, and 26 as well as all intermediates were characterized by elemental analyses, UV and 1H-NMR spectra. The deblocked conjugates 15, 16, and 27 were pure according to HPLC and showed the correct compositions by mass spectra. Comparative biological studies indicated that cordycepincholesterol conjugate trimers 16 and 27 were 333- and 1000-fold, respectively, more potent inhibitors of HIV-1-induced syncytia formation than cordycepin trimer core.
    Additional Material: 1 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19940770707
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  • 84
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    Metal-Ion-Coordinating Properties of a Viral Inhibitor, a pyrophosphate analogue, and a herbicide metabolite, a glycinate analogue: The solution properties of the potentially five-membered chelates derived from phosphonoformic acid and (aminomethyl)phosphonic acid (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 1738-1756 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The pyrophosphoric-acid-analogue phosphonoformic acid (pfa) and the amino-acid-analogue (aminomethyl)phosphonic acid (ampa) both form, in the deprotonated state, i.e., as -OOC-PO32- and H2N—CH2—PO32-, respectively, five-membered chelate rings with metal ions. pfa inhibits both phosphate transport and virus replication, while ampa is a metabolic product of the common herbicide glyphosate ( = N-(phosphonomethyl)glycine). The acidity constants of H2pfa- and H2ampa± as well as the stability constants of the [M(Hpfa)], [M(pfa)]-, [M(Hampa)]+, and [M(ampa)] complexes, where M2+ = Mg2+, Ca2+, Sr2+, Ba2+, Mn2+, Co2+, Ni2+, Cu2+, Cu(2,2′-bipyridyl)2+, Cu(1,10-phenanthroline)2+, Zn2+, or Cd2+, have been determined by potentiometric pH titrations in aqueous solution at 25° and I = 0.1M (NaNO3). The structures of isomeric complexes and the connected intramolecular equilibria are deduced and evaluated based on the equilibrium constants measured and those calculated via the pKa values of the above mentioned ligands and previously established log K vs. pKa straight-line plots (H. Sigel et al., Helv. Chim. Acta 1992, 75, 2634) for a simple phosphonate-M2+ coordination. pfa forms stronger complexes than ampa with all the above mentioned metal ions, with the single exception of [Cu(ampa)] which is slightly more stable than [Cu(pfa)]-. In neutral solutions, more precisely at pH of ca. 6, pfa complexes of alkaline-earth-metal ions retain one phosphonate-bound proton, [M(Hpfa)], while those of the transition-metal ions chelate with the trianionic ligand, pfa3-. In accord with increasing ligand-basicity, the stability-constant order for all metal-ion complexes is oxalate 〉 pfa 〉 pyrophosphate but, owing to proton competition in pyrophosphate, in neutral solutions metal-ion complexation of pfa3- competes with P2O74-. With ampa alkaline-earth-metal ions interact only with the phosphonate group of even the dianionic ligand (though Mg2+ appears to form a low fraction of a [Mg(ampa)] chelate) while transition-metal ions form chelates which are comparable in stability to those of glycinate.
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  • 85
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    X-Ray Crystal Structure of the 2-Phenyladamant-2-yl Cation (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 1773-1780 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The crystal structure of the Sb2F11 salt of the 2-phenyladamant-2-yl cation, 1 · Sb2F11, was determined at 183 K (P21/c, R1 = 0.0652, σ(C—C) = 0.02 Å), because earlier published results indicated a charge delocalization from the cationic C(2) into the σ framework (C—C hyperconjugation) and a bending of the C(2) bridge. In the structure of 1, a displacement of the C(2) bridge by 7.8(12)° from the symmetrical position and C—C bond-length deviations from expectation values were found which are in agreement with preferential C—C hyperconjugation on one face of C(2). The interactions of 1 with two Sb2F11 counterions nearest to C(2) also indicate different behaviour of the two faces of C(2). The benzylic resonance in 1 is confirmed.
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  • 86
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    Facile Preparation of (±)-12-Epiprostaglandins from 7-Oxabicyclo[2.2.1]hept-5-en-2-one via an all-cis-formyllactone related to Corey lactoneA preliminary communication of one part of this work was published [1]. (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 1781-1790 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The bicyclic monoselenoacetal 7, easily obtained from (±)-7-oxabicyclo[2.2.1]hept-5-en-2-one (6) via a radical addition-acyl migration sequence, was converted to racemic 12-epiprostaglandins 3 and 4. The key intermediate was the all-cis-formyllactone 2b related to Corey lactone (see 12; Scheme 1). The presence of a (tert-butyl)-dimethylsilyl protective group for the 11-OH substituent (prostaglandin numbering) was found to be crucial in avoidingβ -elimination and epimerization during the Wittig-Horner reaction (Scheme 2). Epimerization at C(12) at the formyllactone stage (see 2b) was also possible and gave the known precursor 1b of naturally occurring prostaglandins and analogs.
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  • 87
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    Stability of Charge-Transfer Complexes of CS2 with PH3 and its derivatives: Ab initio MRSDCI/CASSCF StudyDedicated to Prof. Jan Linderberg, an excellent theoretician and marvelous friend, on the occasion of his 60th birthday (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 1810-1816 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: While trialkylamines and dialkyl(phenyl)amines do not react with CS2 in the sense of an addition reaction, the analogous phosphines react smoothly. Attempts to interpret the reaction course on the basis of semiempirical, HF, MP2, and MP4 calculations of energy changes failed completely. To understand why Me3P or Me2PhP react so vigorously (liquid phase, 300 K) with CS2, CASSCF and MRSDCI calculations must be carried out.
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  • 88
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    Synthesis and Complexation Properties of a New Class of Receptors based on a cone-configurated tetra-p-(tert-butyl)calix[4]arene and bipyridyl subunits (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 1817-1825 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 0The bipyridyl-armed tetra-p-(tert-butyl)calix[4]arenes 1-5 were synthesized from tetra-p-(tert-butyl)-calix[4]arene A and 6-(bromomethyl)-6′-methyl-2,2′-bipyridine (B) by direct base-strength-driven regioselective O-alkylation or by stepwise procedures. Preliminary complexation studies of the ligands 1-3 with CuI affording the complexes 6-8 are described.
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    URL: http://dx.doi.org/10.1002/hlca.19940770713
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  • 89
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    A Kinetic Analysis of the Reaction Catalysed by (Hydroxymethyl)bilane SynthaseAbbreviations used: FPLC, fast-protein liquid chromatography; HMBS, (hydroxymethyl)bilane synthase; MAD, multiwavelength anomalous diffraction: PBG, porphobilinogen: SeMet, selenomethionine. (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 1791-1809 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (Hydroxymethyl)bilane synthase (HMBS) catalyses the conversion of porphobilinogen (2) into the (hydroxymethyl)bilane derivative 3, a linear tetrapyrrolic intermediate in the biosynthesis of haem, chlorophyll, and related pigments. The conversion involves the sequential formation of four intermediate covalent enzyme-substrate complexes, before the product is released. We analysed the pre-steady-state kinetics of the formation of the complexes, taking advantage of their remarkable chemical stability allowing chromatographic separation. The experimental approach involved the generation of the complexes while HMBS was immobilised on an anion-exchange column. A solution being 0.2 Km in substrate was pumped through the column during a time interval which was varied to sample the pre-steady-state period. Then, the enzyme and enzyme-substrate complexes were eluted and their proportions evaluated. A computer simulation of the pre-steady-state time course, in combination with a χ2 fitting to the experimental data, allowed the specificity constants kcat/Km for the individual steps of the process to be derived. By repeating the analysis with variants of HMBS in which specific amino acids were replaced by others, we demonstrated that it is possible to trace the consequences of amino-acid replacements down to the individual steps of the reaction sequence. Since the positions of the amino acids concerned in the three-dimensional structure were known, detailed structure-function relationships become evident in this way.
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  • 90
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    Preparation and Structure of Oligolides from (R)-3-Hydroxypentanoic Acid and comparison with the hydroxybutanoic-acid derivatives: A small change with large consequencesPart of the projected Ph.D. theses of T.H., F.N.M.K., and U.D.L., ETH-Zürich. (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 2007-2034 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cyclic oligomers of (R)-3-hydroxyvaleric acid (3-HV) are prepared from the monomer by three different methods, giving various ratios of the oligomers. The macrocycles containing three to twelve 3-HV units (12- to 48-membered rings) are isolated in pure form by chromatography. The triolide 3 can be separated by distillation and isolated on large scale. Biopol, the copolymer of (R)-3-hydroxybutanoic acid (3-HB) and (R)-3-hydroxyvaleric acid (3-HV), is degraded to mixtures of Me- and Et-substituted triolides (‘mixolides’) with high crystallization tendency. The X-ray crystal structures of the tetrolide 4, pentolide 5, hexolide 6, heptolide 7, and of two ‘mixolides’ (with inclusions of solvent) have been determined (Figs. 3-7, 10, and 11) and are compared with those of the corresponding 3-HB derivatives reported previously. From the structural data, a 31 and a 21 helix of 3-HV can be modelled, and the latter one compared with helix structures of P9(3-HB) and P(3-HV) derived from stretch-fibre X-ray scattering. Crystals of a water-containing NaSCN complex of the triethyl triolide 3 were obtained in good quality for X-ray analysis. The structure (Figs. 12, 13, and Table 6) contains an interesting array of C=O and H2O O-atoms around the Na+ ions along a channel-type tube (a-axis of the crystal) which may be relevant to the role of P(3-HB) and P(3-HV) as components of cellular ion channels.
    Additional Material: 13 Ill.
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  • 91
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    Synthesis of Tri-, Penta-, and Heptapeptides Containing and (R)-2-alkyl-2-amino-3-(methylamino)-propionic acid residue in the central positionThis project was supported by the Swiss National Science Foundation, project No. 20-30770.91 (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 2035-2050 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: By conventional peptide-coupling methods (C to N direction; mixed anhydride, bis(2)-oxooxazolidin-3-yl)phosphinoyl chloride (Bop-Cl), or dicyclohexylcarbodiimide (DCC), 2-amino-2-methyl-3-(methylamino)-propionic acid and 2-amino-2-ethyl-3-(methylamino)propionic acid ( = 2-amino-2-[(methylamino)methyl]butanoic acid) are incorporated in the central position of tri-, penta-, and heptapeptides (see 3-7, 21, and 22). The fragment coupling of the β -amino group of the diamino-acid moiety in a tetrapeptide led to partial epimerization, and thus, two epimeric heptapeptide derivatives were actually obtained (7 and epi-7). The final deprotection to the free heptapeptide (involving a Me3SiI cleavage of BocNH and MeOCONH, a saponification with NaOH, and HPLC purification) gave both the desired product (isopeptide 21), with the β -amino group inside the peptide backbone, and a product (peptide 22) of transpeptidation, with the α-amino group of the diamino acid incorporated and a (methylamino)methyl group as the side chain. Peptide 22 is completely converted to the isopeptide 21 by prolonged treatment with base. The heptapeptide 21 was analyzed by elaborate 2QF-COSY and NOESY NMR measurements in H2O/CD3OD at -5° (Table, Fig.); there is no indication for β -sheet or helical structures, a fact which was also confirmed by CD measurements.
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  • 92
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    Masthead (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994) 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770801
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  • 93
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    Mitteilungen - Communications (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 2070-2070 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770731
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  • 94
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    Preparation and Transmetallation of a Triphenylstannyl β-D-Glucopyranoside: A highly stereoselective route to β-D-C-glycosides via glycosyl dianions (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 2060-2069 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The triphenylstannyl β-D-glucopyranoside 4 was synthesized in one step from the 1,2-anhydro-α-D-glucopyranose 3 with (triphenylstannyl)lithium (Scheme 1). Transmetallation of 4 with excess BuLi, followed by quenching the dianion 7 with CD3OD gave (1S)-1,5-anhydro-3,4,6-tri-O-benzyl-[1-2H]-D- glucitol (8) in 81% yield (Scheme 2). Trapping of 7 with benzaldehyde, isobutyraldehyde, or acroleine gave the expected β-D-configurated products 11, 12, and 13 in good yields. Preparation of C-acyl glycosides from acid chlorides, such as acetyl or benzoyl chloride was not practicable, but addition of benzonitrile to 7 yielded 84% of the benzoylated product 14. Treatment of 7 with MeI led to 15 (30%) along with 40% of 18, C-alkylation being accompanied by halogen-metal exchange. Prior addition of lithium 2-thienylcyanocuprate increased the yield of 15 to 50% and using dimethyl sulfate instead of MeI led to 77% of 15. No α-D-anomers could be detected, except with allyl bromide as the electrophile, which yielded in a 1:1 mixture of the anomers 16 and 17.
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  • 95
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    C2-Symmetric Bicyclic Diols as Chiral Ligands in the titanate-catalyzed enantioselective addition of alkylzinc reagents to aldehydes (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 2111-2116 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enantiomerically pure C2-symmetric 1,4-diols embodying bicyclic C-frameworks were synthesized by means of asymmetric carbo-Diels-Alder reactions as key steps (Scheme 1). They were investigated as chiral ligands in the enantioselective addition of ZnEt2 to aromatic aldehydes. In the presence of 20-40 mol-% of the titanates formed from these diols and [Ti(i-PrO)4] at -78°, the respective 1-arylpropanols were obtained with enantiomer ratios up to 93:7 (Scheme 2, Table).
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    URL: http://dx.doi.org/10.1002/hlca.19940770803
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  • 96
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    Synthesis of Aristotelia-Type Alkaloids. Part XIIIPart XIII, see [1].. Total syntheses of (+)-makonine, (+)-aristotelinone, and (+)-11,12-didehydroaristoteline (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 2125-2132 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The oxidative transformation of synthetic (+)-aristoteline ((+)-6) into other metabolites which had been isolated from Aristotelia species was investigated. Thus, treatment of (+)-6 with I2 as the single oxidant furnished the naturally occurring indole alkaloids (+)-makonine ((+)-9),(+)-aristotelinone ((+)-11), or (+)-11, 12-didehydroaristoteline ((+)-7) in good yields, the selectivity of the oxidation process depending on the chosen reaction conditions.
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    URL: http://dx.doi.org/10.1002/hlca.19940770805
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  • 97
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    Preparation and Structural Analysis of Several New α,α,α′,α′-Tetraaryl-1,3-dioxolane-4,5-dimethanols (TADDOL's) and TADDOL analogs, their evaluation as titanium ligands in the enantioselective addition of methyltitanium and diethylzinc reagents to benzaldehyde, and refinement of the mechanistic hypothesis (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 2071-2110 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Preparation and screening of twenty new ligands, all analogs of α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5-dimethanol (TADDOL), for the Ti-catalyzed asymmetric addition of methyltri(isopropoxy)titanium and diethylzinc to benzaldehyde are described. These ligands have the dioxolane ring of the TADDOL's replaced by cyclobutane, cyclopentane, cyclohexene, cyclohexane, bicyclo[2.2.1]heptene and -heptane and bicyclo[2.2.2]octene and -octane moieties; several have H-atoms or alkyl groups in place of the aryl groups, and nine of them have C2 symmetry. X-Ray crystallography and molecular mechanics are used to analyze the structure of the ligands, and two structural features appear to correlate with selectivity: (i) the torsion angle for the chelating O-atom and the ortho-C-atom of the axial Ph group (a small, ca. 19°, angle is optimum, Fig.8) and (ii) the “degree of perpendicularity” of the axial Ph group (Fig. 9). Competition experiments indicate that TADDOL 1a catalyzes both the methyltitanium and diethylzinc additions ≥ 50 times faster than the related dioxolane analogs 12a, 12c, and 12e (Scheme 7), indicating that both axial and equatorial aryl groups (see Footnote 6) are necessary for ligand-accelerated catalysis of these reactions. A refined mechanistic hypothesis is presented (Fig. 10) to explain the selectivities observed for these new ligands. Our analysis suggests that a combination of structural features appear necessary for good catalytic efficiency and high selectivity. These features, especially the rather subtle conformational effects, appear to be optimized (among the ligands tested) in the TADDOL's.
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  • 98
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    Quantum Chemical Investigation of the Structure and Reactivity of Indole Derivatives of Tricarbonylchromium(0) (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 2117-2124 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In a theoretical investigation of the structure and reactivity of indole derivatives of tricarbonylchromium(0), we have used two different semi-empirical quantum chemical models derived from the extended Hückel molecular-orbital (EHMO) formalism. The first one, based on the atom-superposition and electron-delocalization (ASED) method, is used to optimize the geometry of the systems; it is shown to lead to results in satisfactory agreement with experiment in the case of the complex for which X-ray structural data are available, the average errors being 0.03-0.05 Å for bond distances and 5° for bond angles. The second one consists of a local reactivity index, made of the intermolecular interaction energy between the organometallic substrate and a model reactant. It is seen that this procedure is able to reproduce the experimental trends as to the most reactive regions of the systems investigated towards nucleophilic and electrophilic addition reactions.
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  • 99
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    Synthesis and Addition Reactions of 1,3-Thiazole-5(4H)-thione OxidesDedicated to Prof. Dr. Fritz Sauter on the occasion of his 65th birthday (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 2133-2141 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,3-Thiazole-5(4H)-thione oxides 2 were prepared by oxidation of the corresponding 1,3-thiazole-5(4H)-thiones 1 with m-chloroperbenzoic acid (Table 1). Addition reactions of 2 with organolithium and Grignard reagents yielded 4,5-dihydro-4,4-dimethyl-1,3-thiazol-5-yl methyl sulfoxides of type 4 via thiophilic attack (Table 2). Whereas the reaction with the organolithium compounds proceeded with fair-to-excellent yields, the Grignard reagents reacted only very sluggishly. The sulfoxides 4 could also be prepared via oxidation of 4,5-dihydro-4,4-dimethyl-5-(methylthio)-1,3-thiazoles of type 3 with m-chloroperbenzoic acid, together with the corresponding sulfones 5 (Scheme 1).
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    URL: http://dx.doi.org/10.1002/hlca.19940770806
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  • 100
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    Glycosylidene Carbenes. Part 15. Synthesis of disaccharides from allopyranose-derived vicinal 1,2-diols. Evidence for the protonation by a H-bonded hydroxy group in the σ-plane of the intermediate carbene, followed by attack on the oxycarbenium ion in the π-plane (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 334-350 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The α-D-allo-diol 9 possesses an intramolecular H-bond (HO—C(3) to O—C(1)) in solution and in the solid state (Fig. 2). In solution, it exists as a mixture of the tautomers 9a and 9b (Fig. 3), which possess a bifurcated H-bond, connecting HO—C(2) with both O—C(1) and O—C(3). In addition, 9a possesses the same intramolecular H-bond as in the solid state, while 9b is characterized by an intramolecular H-bond between HO—C(3) and O—C(4). In solution, the β-D-anomer 12 is also a mixture of tautomers, 12a and presumably a dimer. The H-bonding in 9 and 12 is evidenced by their IR and 1H-NMR spectra and by a comparison with those of 3-8, 10, and 11. The expected regioselectivity of glycosidation of 9 and 12 by the diazirine 1 or the trichloroacetimidate 2 is discussed on the basis of the relative degree of acidity/nucleophilicity of individual OH groups, as governed by H-bonding. Additional factors determining the regioselectivity of glycosidation by 1 are the direction of carbene approach/proton transfer by H-bonded OH groups, and the stereoelectronic control of both the proton transfer to the alkoxy-alkyl carbene (in the σ-plane) and the combination of the thereby formed ions (π-plane of the oxycarbenium ion). Glycosidation of 9 by the diazirine 1 or the trichloroacetimidate 2 proceeded in good yields (75-94%) and with high regioselectivity. Glycosidation of 9 and 12 by 1 or 2 gave mixtures of the disaccharides 14-17 and 18-21, respectively (Scheme 2). As expected, glycosidation of 12 by 1 or by 2 gave a nearly 1:1 mixture of regioisomers and a slight preference for the β-D-anomers (Table 4). Glycosidation of the α-D-anomer 9 gave mostly the 1,3-linked disaccharides 16 and 17 (α-D β-D) along with the 1,2-linked disaccharides 14 and 15 (α-D 〈 β-D, 1,2-/1,3-linked glycosides ca. 1:4), except in THF and at low temperature, where the β-D-configurated 1,2-linked disaccharide 15 is predominantly formed. Similarly, glycosidation of 9 with 2 yielded mainly the 1,3-linked disaccharides (1,2-/1,3-linked products ca. 1:3 and α-D/β-D ca. 1:4). Yields and selectivity depend upon the solvent and the temperature. The regioselectivity and the unexpected stereoselectivity of the glycosidation of 9 by 1 evidences the combined effect of the above mentioned factors, which also explain the lack of regio-complementarity in the glycosidation of 9 by 1 and by 2 (Scheme 3). THF solvates the intermediate oxycarbenium ion, as evidenced by the strong influence of this solvent on the regio- and stereoselectivity, particularly at low temperatures, where kinetic control leads to a stereoelectronically preferred axial attack of THF on the oxycarbenium ion.
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    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770133
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