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  • 1985-1989  (6,134)
  • 1965-1969  (3,216)
  • Organic Chemistry  (6,621)
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  • 1
    Electronic Resource
    Electronic Resource
    Oro-facial dyskinesia and the sub-commissural part of the globus pallidus in the cat: role of acetylcholine and its interaction with GABA (1989)
    Springer
    Psychopharmacology 99 (1989), S. 381-385 
    Details
    ISSN: 1432-2072
    Keywords: Oro-facial dyskinesia ; Globus pallidus ; GABA ; Acetylcholine ; Behaviour ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The possible role of cholinergic mechanisms in the sub-commissural part of the globus pallidus (scGP) in the induction of oro-facial dyskinesia (OFD) was studied in cats. Local injections of the cholinergic agonist carbachol into the scGP elicited tongue protrusions in a dose dependent way (100–1000 ng/0.5 μl). The effect elicited by 1000 ng carbachol was selectively antagonized by the cholinergic antagonist scopolamine (10 μg/0.5 μl); this dose of scopolamine was ineffective when injected alone. The tongue protrusions resulted from both normal and abnormal movements: whereas normal movements simply consisted of protruding the flat tongue, abnormal movements implied a variety of movements, especially curling upwards the lateral side(s) or tip of the tongue inside or outside the oral cavity. The abnormal carbachol-induced tongue protrusions formed part of a syndrome marked by dyskinetic movements of the muscles of the eye, ear and cheek, and were identical to those seen previously after local injections of picrotoxin (250–500 ng). Intra-pallidal injections of the abovementioned dose of scopolamine had no effect on the tongue protrusions induced by local injections of 375 ng picrotoxin. However, local injections of 100 ng muscimol, which was previously found to attenuate significantly the effect of 375 ng picrotoxin and which was ineffective when injected alone, significantly attenuated the tongue protrusions induced by local injections of 1000 ng carbachol. These data suggest that the cholinergic effects are mediated via a GABAergic mechanism, but not vice versa. The results are discussed in view of GABAergic and anticholinergic therapies used in oro-facial dyskinesia.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00445562
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  • 2
    Electronic Resource
    Electronic Resource
    Synaptic potentials induced by postganglionic stimulations in cat bladder parasympathetic neurones (1989)
    Springer
    Pflügers Archiv 414 (1989), S. 235-244 
    Details
    ISSN: 1432-2013
    Keywords: Cat ; Urinary bladder ; Parasympathetic ganglion neurone ; Postganglionic stimulation ; Synaptic potentials
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Intracellular recording techniques were used to examine and compare synaptic potentials evoked by stimulating pre- and postganglionic nerve trunks in cat bladder parasympathetic ganglia. In the 76 ganglion cells exammed, two types of responses were recorded on stimulating the postganglionic nerve: an antidromic action potential (type Post NS1;n=30) or a fast excitatory postsynaptic potential (f-EPSP; type PostNS2;n=46) which resulted in an orthodromic-like action potential. In some of the cells exhibiting a PostNS1 response (n=19), a fast depolarization was superimposed on the antidromic spike. This depolarization was due to the synaptic activation of nicotinic receptors. In many of the cells exhibiting either PostNS1 or PostNS2 responses, repetitive stimulation of the postganglionic nerve induced a slow hyperpolarization. Applying nicotinic (hexamethonium, methonium, 0.5–1 mM), muscarinic (atropine, 1 μM), alpha-adrenergic (phentolamine, 1 μM) and purinergic (caffeine, 0.5–1 mM) receptor antagonists completely inhibited the tetanus-induced slow hyperpolarization in some cells (n=5). In other cells (n=15), a slow hyperpolarization persisted in the presence of these antagonists. These results indicate that stimulation of the postganglionic nerve trunk of cat bladder parasympathetic ganglia can elicit not only an antidromic action potential, but also synaptic potentials which are mediated by the activation of cholinergic (nicotinic and muscarinic), noradrenergic and purinergic receptors, as well as a non-cholinergic, non-alpha-adrenergic and non-purinergic synaptic potential.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00580969
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  • 3
    Electronic Resource
    Electronic Resource
    [3H]ICS 205-930 labels 5-HT3 recognition sites in membranes of cat and rabbit vagus nerve and superior cervical ganglion (1989)
    Springer
    Naunyn-Schmiedeberg's archives of pharmacology 340 (1989), S. 396-402 
    Details
    ISSN: 1432-1912
    Keywords: 5-HT3 receptors ; Radioligand binding ; [3H]ICS 205-930 ; Cat ; Rabbit ; Vagus nerve ; Superior cervical ganglion
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The binding characteristics of [3H]ICS 205-930, a 5-hydroxytryptamine 5-HT3 receptor antagonist, were investigated in membranes prepared from cat and rabbit vagus nerve (VN) and superior cervical ganglion (SCG). The autoradiographic localisation of 5-HT3 recognition sites was also assessed using [3H]ICS 205-930 in slices from cat medulla oblongata, nodose ganglion and vagus nerve. [3H]ICS 205-930 bound to a homogeneous population of high affinity recognition sites in cat VN: Bmax = 201 ± 43 fmol/mg protein, pKD = 9.26 ± 0.17 and SCG: Bmax = 291 ± 40 fmol/mg, pKD = 9.35 ± 0.80 (n = 3). Competition experiments performed in membranes from cat VN and SCG with agonists and antagonists suggested the presence of a homogeneous population of [3H]ICS 205-930 recognition sites. Competition curves were steep and monophasic and were best fitted by a 1 receptor site model. The following rank order of affinity for [3H]ICS 205-930 binding sites was observed with antagonists: SDZ 206-830 = ICS 205-930 〉 BRL 43694 〉 SDZ 206–792 〉 quipazine 〉 MDL 72222 〉 metoclopramide 〉 mCPP and agonists: 2-methyl-5-HT = 5-HT 〉 phenylbiguanide. A similar profile was observed for a limited series of compounds in rabbit membranes. Drugs acting at 5-HT1, 5-HT2 and dopamine receptors (domperidone, spiperone and metergoline) showed very low affinities for [3H]ICS 205-930 recognition sites. The sites labelled with [3H]ICS 205-930 in vagus nerve and superior cervical ganglion of both species displayed the pharmacological profile of a 5-HT3 receptor. There was a significant correlation between the rank order of affinity of the tested compounds for [3H]ICS 205-930 recognition sites in cat and rabbit membranes and their rank order of affinity for 5-HT3 receptors from neuroblastoma-glioma NG 108-15 cells. Autoradiographic studies suggest that [3H]ICS 205-930 binding sites are present over and around the nodose ganglion cell somata, along certain fibers of the vagus nerve and in the terminal areas of this nerve in the medullar nucleus of the vagus. The present data demonstrate that [3H]ICS 205-930 identifies 5-HT3 receptors in preparations of cat and rabbit vagus nerve and superior cervical ganglion.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00167040
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  • 4
    Electronic Resource
    Electronic Resource
    Carotid occlusion increases the release of endogenous GABA in the nucleus of the solitary tract (1989)
    Springer
    Naunyn-Schmiedeberg's archives of pharmacology 340 (1989), S. 764-766 
    Details
    ISSN: 1432-1912
    Keywords: Nucleus of the solitary tract (NTS) ; GABA release ; Carotid occlusion ; Blood pressure ; Push-pull cannula ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In anaesthetized cats, the nucleus of the solitary tract was bilaterally superfused through push-pull cannulae with artificial cerebrospinal fluid (CSF) and the effect of carotid occlusion on the release of endogenous GABA was investigated. Bilateral carotid occlusion led to a rise in blood pressure which was associated with a very pronounced increase in the release rate of GABA in the nucleus of the solitary tract. The results demonstrate the hypertensive function of GABA in the nucleus of the solitary tract and the importance of GABAergic neurons of this nucleus for the central cardiovascular control.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00169687
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  • 5
    Electronic Resource
    Electronic Resource
    Neurovisceral sphingomyelinosis in a Siamese cat (1989)
    Springer
    Acta neuropathologica 79 (1989), S. 330-332 
    Details
    ISSN: 1432-0533
    Keywords: Sphingomyelinosis ; Neuropathology ; Histochemistry ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary This report presents the clinical, morphological and biochemical findings on an 11-month-old female Siamese cat with neurovisceral sphingomyelinosis. Gross pathological features and histochemical findings are compared with the human disease counterpart and the previously described animal models. Hepatomegaly was observed while splenomegaly was not. Although sphingomyelin in liver and spleen was biochemically elevated, histochemical results in this case were slightly different from those previously recorded in human and feline Niemann-Pick disease. These results suggest that this feline case might be a different type of animal Niemann-Pick disease to that reported previously.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00294670
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  • 6
    Electronic Resource
    Electronic Resource
    The cerebellar nuclear afferent and efferent connections with the lateral reticular nucleus in the cat as studied with retrograde transport of WGA-HRP (1989)
    Springer
    Anatomy and embryology 179 (1989), S. 471-483 
    Details
    ISSN: 1432-0568
    Keywords: Lateral reticular nucleus ; Cerebellar nuclei ; Retrograde transport of WGA-HRP ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The cerebellar nuclear projection from the lateral reticular nucleus (NRL) was studied in 29 cats by means of retrograde axonal transport after implantation of the crystalline wheat germ agglutinin-horseradish peroxidase (WGA-HRP) complex in the cerebellar nuclei. It was confirmed that all the cerebellar nuclei receive afferent fibres from the NRL with the strongest termination in the ipsilateral interposed nuclei. In addition, these experiments give evidence of a previously unrecognized topical pattern in the projection to the interposed nuclei, arranged according to the same principle as in the projection to the immediately overlying cerebellar cortex. Thus, the anterior interposed nucleus receives fibres from all parts of the main NRL, its rostral part especially from laterally situated neurons, while subsequent more caudal parts from more medially situated neurons, while the posterior interposed nucleus receives fibres mainly from the dorsomedial part of the main NRL. The cerebellar nuclear projection to the NRL was investigated in 15 cats using retrograde transport after ventral microiontophoretical ejections of the WGA-HRP complex in the main NRL. The contralateral rostral fastigial nucleus was confirmed as the main origin of this projection, but projecting neurons were, in addition, discovered rostrally in the anterior interposed and dentate nuclei on the same side. No topical differences could be observed following ejections in different parts of the NRL; the majority of the projecting neurons were always concentrated along the ventral and lateral borders of the fastigial nucleus and in the adjacent medial part of the anterior interposed nucleus.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00319590
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  • 7
    Electronic Resource
    Electronic Resource
    Response to rates of luminance change of sustained and transient cells in the cat lateral geniculate nucleus and optic tract (1989)
    Springer
    Experimental brain research 74 (1989), S. 116-130 
    Details
    ISSN: 1432-1106
    Keywords: Lateral geniculate nucleus ; Optic tract ; Sustained cells ; Transient cells ; Temporal luminance modulation ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary We recorded the response of sustained (X) and transient (Y) cells in the cat lateral geniculate nucleus (LGN) and optic tract to a stationary spot while the spot luminance was increased and decreased with a constant rate (linear luminance functions), or modulated sinusoidally. The spot filled the receptive field center, and was surrounded by an annulus of fixed luminance. The LGN X cells seemed to perform a differentiation-like operation in the time domain at slow temporal modulations, giving information about rate of luminance change. To the linear luminance functions the cells responded with a constant firing rate. The on-center cells were activated during increasing luminance, the off-center cells during decreasing luminance. This firing rate increased monotonically with rate of luminance change. To low-frequency sinusoidal modulations the cells had a marked negative phase shift. The response of the LGN Y cells had a transient component shortly after the luminance started to increase (on-center cells) or decrease (off-center cells), followed by a secondary, gradually changing component. The peak of the transient component occurred on average when the response of the X cells increased most rapidly. To low-frequency sinusoidal modulation the average negative phase shift of this peak was twice the average of the X cells. The Y system could accordingly provide information about rate of change in the response of the X system. In the optic tract the X fiber response resembled the LGN X cell response in most respects. The Y fibers had only a weak transient response component, so this component was accentuated in the thalamic relay. Also the sensitivity for rate of luminance change was increased in LGN.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00248285
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  • 8
    Electronic Resource
    Electronic Resource
    Note on the tonotopic organization in the cat medial geniculate body: influence of sampling of units (1989)
    Springer
    Experimental brain research 74 (1989), S. 220-226 
    Details
    ISSN: 1432-1106
    Keywords: Cat ; Medial geniculate body ; Hearing ; Tonotopic organization ; Single unit recording
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The tonotopic organization observed in the present study for the pars lateralis (LV) of the medial geniculate body (MGB) in nitrous oxide anesthetized cats is generally consistent with that previously reported under barbiturate anesthesia. The present data, however, provide evidence for local deviations in characteristic frequency (CF) using appropriate sampling procedures of single units. Although the majority of pairs of units recorded simultaneously with the same microelectrode showed comparable CFs, a few pairs of such neighbouring units displayed CF disparities of up to 1.5 octaves. In addition, some units characterized by an elevated threshold had a CF deviating significantly from the general CF progression observed for the majority of units having low thresholds. This study points out the influence of the sampling procedure on the quality of the tonotopic organization observed in the MGB in addition to a possible effect of the level of anesthesia.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00248295
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  • 9
    Electronic Resource
    Electronic Resource
    Short latency somaesthetic responses in motor cortex, transmitted through the spino-thalamic system, in the cat (1989)
    Springer
    Experimental brain research 75 (1989), S. 639-643 
    Details
    ISSN: 1432-1106
    Keywords: Motor cortex ; Somaesthetic responses ; Spinothalamic system ; Intracellular recording ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Evidence is presented that in the cat, the spinothalamic system contributes to short latency somaesthetic responses in motor cortex efferent cells. Intracellular recordings performed on identified pyramidal tract cells and corticospinal cells show that these cells are still activated and/or inhibited from the periphery after a set of central nervous lesions leaving intact only the ventral half of the spinal cord. The responses were attributed to the spinothalamic system. The ascending system is activated through collaterals of afferent fibres running in the dorsal columns of the spinal cord. This peripheral link to the motor cortex might participate in updating the motor command on the basis of information feedback from the periphery.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00249915
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  • 10
    Electronic Resource
    Electronic Resource
    Unitary characteristics of presumptive cholinergic tegmental neurons during the sleep-waking cycle in freely moving cats (1989)
    Springer
    Experimental brain research 76 (1989), S. 519-529 
    Details
    ISSN: 1432-1106
    Keywords: Pontine tegmentum ; Cholinergic neurons ; Single units ; Sleep-waking states ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary A total of 260 neurons were recorded in the rostral pontine tegmentum of freely moving cats during the sleep-waking cycle. Of these, 207 neurons (80%) were located in the dorsal pontine tegmentum containing monoaminergic and choline acetyltransferase (ChAT)-immunoreactive, or cholinergic neurons. In addition to presumably monoaminergic PS-off cells (n = 51) showing a cessation of discharge during paradoxical sleep (PS) and presumably cholinergic PGO-on cells (n = 40) exhibiting a burst of discharge just prior to and during ponto-geniculo-occipital (PGO) waves, we observed tonic (n = 108) and phasic (n = 61) neurons exhibiting, respectively, tonic and phasic patterns of discharge during wakefulness and/or paradoxical sleep. Of 87 tonic cells histologically localized in the dorsal pontine tegmentum rich in cholinergic neurons, 46 cells (53%) were identified as giving rise to ascending projections either to the intralaminar thalamic complex (n = 26) or to the ventrolateral posterior hypothalamus (n = 13) or to both (n = 9). Two types of tonic neurons were distinguished: 1) tonic type I neurons (n = 28), showing a tonic pattern and high rates of discharge during both waking and paradoxical sleep as compaired with slow wave sleep; and 2) tonic type II neurons (n = 20), exhibiting a tonic pattern of discharge highly specific to the periods of paradoxical sleep. Tonic type I neurons were further divided into two subclasses on the basis of discharge rates during waking: a) rapid (Type I-R; n = 17); and b) slow (Type I-S; n = 11) units with a discharge frequency of more than 12 spikes/s or less than 5 spikes/s, respectively. Like monoaminergic PS-off and cholinergic PGO-on cells, both tonic type II and type I-S cells were characterized by a long spike duration (median: 3.3 and 3.5 ms), as well as by a slow conduction velocity (median: 1.8 and 1.7 m/s). In the light of these data, we discuss the possible cholinergic nature and functional significance of these ascending tonic neurons in the generation of neocortical electroencephalographic desynchronization occurring during waking and paradoxical sleep.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00248908
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  • 11
    Electronic Resource
    Electronic Resource
    Modulation of short latency cutaneous excitation in flexor and extensor motoneurons during fictive locomotion in the cat (1989)
    Springer
    Experimental brain research 77 (1989), S. 57-68 
    Details
    ISSN: 1432-1106
    Keywords: Cutaneous EPSPs ; Fictive locomotion ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary We examined modulation of transmission in short-latency, distal hindlimb cutaneous reflex pathways during fictive locomotion in 19 decerebrate cats. Fictive stepping was produced either by electrical stimulation of the mesencephalic locomotor region (MLR) or by administration of Nialamide and 1-DOPA to acutely spinalized animals. Postsynaptic potentials (PSPs) produced by electrical stimulation of low threshold afferents (〈 2.5 times threshold) in the superficial peroneal (SP), sural, saphenous or medial plantar nerves were recorded intracellularly from various extensor (n = 28) and flexor (n = 24) motoneurons and averaged throughout the step cycle, together with voltage responses to intrasomatic constant current pulses (in order to monitor relative cell input resistance). Each motoneuron studied displayed rhythmic background oscillations in membrane potential and correlated variations in input resistance. The average input resistance of extensor motoneurons was lowest during mid-flexion, when the cells were relatively hyperpolarized and silent. Conversely, average input resistance of flexor motoneurons was highest during mid-flexion, when they were depolarized and active. The amplitude of the minimum-latency excitatory components of PSPs produced by cutaneous nerve stimulation were measured from computer averaged records representing six subdivisions of the fictive step cycle. Oligosynaptic EPSP components were consistently modulated only in the superficial peroneal responses in flexor motoneurons, which exhibited enhanced amplitude during the flexion phase. With the other skin nerves tested (sural, saphenous, and plantar), no consistent patterns of modulation were observed during fictive locomotion. We conclude that transmission through some, but not all, oligosynaptic excitatory cutaneous pathways is enhanced by premotoneuronal mechanisms during the flexion phase of fictive stepping in several cat hindlimb motor nuclei. The present results suggest that the patterns of interaction between the locomotor central pattern generator and excitatory cutaneous reflex pathways depend on the source of afferent input and on the identity of the target motoneuron population.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00250567
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  • 12
    Electronic Resource
    Electronic Resource
    Central distributions of the efferent and afferent components of the pharyngeal branches of the vagus and glossopharyngeal nerves: an HRP study in the cat (1989)
    Springer
    Experimental brain research 78 (1989), S. 327-335 
    Details
    ISSN: 1432-1106
    Keywords: Pharyngeal vagus nerve ; Pharyngeal glossopharyngeal nerve ; Nucleus ambiguus ; Retrofacial nucleus ; Lateral reticular formation ; Nucleus of solitary tract ; Alaminar spinal trigeminal nucleus ; Horseradish peroxidase ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The central distributions of efferent and afferent components of the pharyngeal branches of the vagus (PH-X) and glossopharyngeal (PH-IX) nerves in the cat were studied by soaking their central cut ends in a horseradish peroxidase (HRP) solution. HRP-labelled PH-X neurones were distributed ipsilaterally in the rostral part of the nucleus ambiguus (NA) and the retrofacial nucleus (RFN); HRP-labelled PH-IX neurones were found in the ipsilateral RFN and the bulbopontine lateral reticular formation (RF). Vagal pharyngeal neurones constituted a large population of brainstem motoneurones. The population of HRP-labelled glossopharyngeal neurones was divided into two components. Indeed, on the basis of their location and somal morphology, the most ventral cells were identified as cranial motoneurones and those scattered in the lateral RF as parasympathetic preganglionic neurones. Application of HRP to the PH-IX nerve resulted also in the labelling of fibres and terminals in the alaminar spinal trigeminal nucleus and the nucleus of the solitary tract (NTS). The afferent fibres entered the lateral medulla with the glossopharyngeal roots, ran dorsomedially, then turned caudally toward the NTS and the caudal part of the alaminar spinal trigeminal motor (V) nucleus. In the NTS, labelled fibres ran mainly along the solitary tract, projecting to terminals in the dorsal and dorsolateral nuclei of the NTS.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00228904
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  • 13
    Electronic Resource
    Electronic Resource
    Eye movements evoked by microstimulations in the brainstem of the alert cat (1989)
    Springer
    Experimental brain research 77 (1989), S. 94-102 
    Details
    ISSN: 1432-1106
    Keywords: Eye movement ; Brainstem ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary This study maps the eye movements evoked by microstimulations in the medulla of 9 alert cats. Trains of square waves (20 μA amplitude, 0.2 msec duration, 200 Hz) were delivered through glass-covered tungsten microelectrodes (0.5–1 MΩ). Movements of both eyes were recorded by the magnetic field/eye coil technique. Stimulation of the prepositus hypoglossi nucleus (PH) evoked nystagmus with ipsilaterally-directed slow phases followed by after-nystagmus with contralaterally-directed slow phases. Stimulation of the medial vestibular nucleus (MVN) induced nystagmus whose slow phases were more often ipsilaterally-directed but at time contralaterally-directed. At nearly all sites where we stimulated the reticular formation underlying prepositus and vestibular nuclei (from P4.5 to P12), we recorded versional conjugate movements. They were most often ipsilaterally-directed. Some microstimulations in the region of the medial longitudinal fasciculus evoked recentering eye movements: regardless of the initial position of the gaze (to the left as well as to the right), microstimulations given at the same place induced a movement of both eyes toward their neutral position. The amplitude of this movement was proportional to the eccentricity of the pre-stimulation position of the gaze.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00250571
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  • 14
    Electronic Resource
    Electronic Resource
    Pharyngeal motoneurones: respiratory-related activity and responses to laryngeal afferents in the decerebrate cat (1989)
    Springer
    Experimental brain research 78 (1989), S. 336-344 
    Details
    ISSN: 1432-1106
    Keywords: Vagal pharyngeal nerve ; Glossopharyngeal nerve ; Single fibre recordings ; Respiratory-related units ; Superior laryngeal nerve ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In decerebrate, paralyzed and artificially ventilated cats, we recorded the discharge of 64 motor axons supplying the pharyngeal muscles. Filaments containing motor axons, with discharges related to the respiratory cycle (phrenic nerve activity), were teased from the pharyngeal branches of the vagus and glossopharyngeal nerves. Most units (n = 41) fired only during expiration and exhibited a steady, a decreasing or a late augmenting discharge pattern. These units were found only in vagal filaments. Twenty three units discharged during inspiration and exhibited a steady, a late augmenting or a tonic discharge pattern. The inspiratory-related units were present in both the vagus (n=13) and glossopharyngeal (n=10) nerves. Nineteen of 20 pharyngeal inspiratoryrelated units tested were activated at short latency (range 3.4 to 8.0 ms) by stimulation of afferents in the superior laryngeal nerve (SLN). In 13 of these, such stimulation also suppressed their spontaneous activity. SLN stimulation elicited in all 17 pharyngeal expiratory-related units tested a short latency (range 0 to 8 ms) reduction of activity, followed in 7 units by an increase in activity. SLN stimulation occasionally evoked single or rhythmic multifibre bursts in the vagal pharyngeal filaments. These bursts, involving expiratory-related units, likely correspond to the buccopharyngeal stage of swallowing.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00228905
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  • 15
    Electronic Resource
    Electronic Resource
    Orientation bias of cat retinal ganglion cells: a reassessment (1989)
    Springer
    Experimental brain research 76 (1989), S. 182-186 
    Details
    ISSN: 1432-1106
    Keywords: Retinal ganglion cells ; Orientation bias ; Receptive field centre ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary For cat retinal ganglion cells whose receptive field centres were distributed in specified sections of the left visual field, the deviations of the major axis from the radial, horizontal, and circumferential directions were determined. The percentage of cells with deviations within ± 20° from the radial, horizontal, and circumferential directions were, respectively, 33%, 68%, 16%. In addition, comparison between values of deviation from the horizontal direction for cells located at eccentricities of 10° and 20° from the area centralis showed a statistically significant trend: the bias for the horizontal increased with eccentricity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00253635
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  • 16
    Electronic Resource
    Electronic Resource
    The role of inhibitory processes in the formation of functional properties of neurons in vibrissal projection zone of the cat somatosensory cortex (1989)
    Springer
    Experimental brain research 76 (1989), S. 198-206 
    Details
    ISSN: 1432-1106
    Keywords: Somatosensory cortex ; Directional sensitivity ; GABA inhibition ; Picrotoxin ; Bicuculline ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The role of intracortical inhibitory processes in the formation of neuronal receptive fields in the vibrissal projection zone of the somatosensory cortex was studied. Iontophoretic application of picrotoxin and bicuculline blocks the inhibition and causes the loss of directional sensitivity in neurons. Activation of inhibition by distant glutamate application gives opposite results — neurons become direction sensitive. A dependence was found between spatial location of activated cells and the pattern of changes of their detector properties. Inhibitory processes caused by natural afferent stimulation lead to similar changes in the functional properties of neurons.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00253637
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  • 17
    Electronic Resource
    Electronic Resource
    Quantitative measurements of receptive field changes during antagonism of GABAergic transmission in primary somatosensory cortex of cats (1989)
    Springer
    Experimental brain research 78 (1989), S. 514-532 
    Details
    ISSN: 1432-1106
    Keywords: Bicuculline ; Inhibition ; Latency ; Receptive field profile ; Somatosensory cortex ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In cortical area 3b of cats, responses of 76 single neurons to punctate indentations were recorded before and during iontophoretic administration of bicuculline methiodide (BMI), a GABAergic antagonist, at levels that did not affect spontaneous activity. Constant amplitude indentations were applied to selected sites along distalproximal and radial-ulnar axes that intersected the most sensitive area in the receptive field. Profiles of response magnitudes were used to measure receptive field dimensions before and during antagonism of GABAergic inhibition. Blockade of GABAergic transmission caused receptive field dimensions of 48 rapidly-adapting neurons to increase an average 141%, or nearly 2.5 times their original size. Analysis of the spatial distribution of inhibition indicated that in-field inhibition was larger than surround inhibition. During BMI administration, response latency was significantly longer for response elicited from the expanded territory than for responses elicited from within the original receptive field, suggesting that receptive field expansion might be mediated by multisynaptic intracortical connections. The magnitude of receptive field expansion was independent of receptive field size or peripheral location. In a substantial number of neurons, however, BMI produced asymmetric expansions that extended only in the proximal direction. For 9 slowly-adapting neurons, BMI produced measureable increases in receptive field dimensions, but these changes were significantly smaller than the changes in rapidly-adapting neurons.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00230239
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  • 18
    Electronic Resource
    Electronic Resource
    The effects of postsynaptic inhibition on the monosynaptic reflex of the cat at different levels of motoneuron pool activity (1989)
    Springer
    Experimental brain research 77 (1989), S. 577-584 
    Details
    ISSN: 1432-1106
    Keywords: Motoneuron pool ; Inhibition ; Monosynaptic reflex ; Recruitment level ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The motoneurons to the Soleus muscle in the decerebrate cat were activated by the crossed extensor reflex, elicited by stimulation of the contralateral common peroneal (CP) nerve. Monosynaptic reflexes were obtained from the Soleus motoneuron pool by stimulation of the cut L7-S1 dorsal roots. The amplitude of the reflex increased approximately linearly with the recruitment level of the motoneuron pool. Tonic postsynaptic inhibition was induced in the Soleus moto-neuron pool by repetitive antidromic stimulation of the Lateral Gastrocnemius (LG) and Medial Gastrocnemius (MG) nerves at a rate of 17–47 stimuli/s. This reduced the size of the monosynaptic reflex at rest by at least 40%. However, when the motoneurons were active, the amplitude of the monosynaptic reflex obtained during repetitive stimulation of the LG-MG nerve increased with the recruitment level along the same curve as the control reflexes. Thus, tonic postsynaptic inhibition of the motoneurons per se cannot control the amplitude of the monosynaptic reflex independently of the recruitment level of the motoneuron pool. These experimental results verify predictions from computer simulations and suggest by exclusion that presynaptic inhibition is needed to control the amplitude of the monosynaptic reflex independently of the recruitment level of the motor pool.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00249610
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  • 19
    Electronic Resource
    Electronic Resource
    Intercostal and abdominal muscle afferent influence on caudal medullary expiratory neurons that drive abdominal muscles (1989)
    Springer
    Experimental brain research 78 (1989), S. 219-222 
    Details
    ISSN: 1432-1106
    Keywords: Control of respiration ; Intercostal muscle afferents ; Phrenic nerve ; Abdominal muscle afferents ; Expiratory neurons ; Abdominal muscle control ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Our objective was to determine if caudal ventral respiratory group (VRG) expiratory (E) neurons that drive abdominal expiratory motoneurons in the lumbar cord respond to intercostal and lumbar nerve afferent stimulation. Results showed that 92% of medullary E-neurons that were antidromically activated from the upper lumbar cord reduced their activity in response to stimulation of external and internal intercostal and lumbar nerve afferents. We conclude that afferent information from intercostal and abdominal muscle tendon organs has an inhibitory effect on caudal VRG E-neurons that drive abdominal expiratory motoneurons.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00230702
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  • 20
    Electronic Resource
    Electronic Resource
    Behavioural thermosensitivity after bilateral lesions of the lateral funiculi in the cervical spinal cord of the cat (1989)
    Springer
    Experimental brain research 78 (1989), S. 374-379 
    Details
    ISSN: 1432-1106
    Keywords: Thermosensitivity ; Spinal cord ; Ascending pathways ; Behaviour ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The behavioural thermosensitivity of six cats was measured before and after single stage, symmetrical, bilateral, surgical lesions of the cervical spinal cord. The lesions were aimed at an area in the most ventral parts of the dorsal halves of the lateral funiculi. Unilateral lesions of that area have previously been found to cause reproducible, although subtotal, contralateral thermosensory defects, which were attributed to interruption of the thermosensory spinothalamic pathway. The lesions of three of the present cats were found to be incomplete, and those animals showed no postoperative thermosensory deficiency. Two of the cats with complete lesions showed marked post-operative defects, especially immediately after the operations, but the third cat with a complete lesion showed no postoperative thermosensory defect at all. The differences between the last three animals have been compared to the irregularity of previous reports about thermosensitivity after spinal cord lesions in man and animals, and may depend on the testing technique, rather than differences of thermosensitivity per se.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00228909
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  • 21
    Electronic Resource
    Electronic Resource
    The distribution of intrinsic cortical axons in area 3b of cat primary somatosensory cortex (1989)
    Springer
    Experimental brain research 78 (1989), S. 501-513 
    Details
    ISSN: 1432-1106
    Keywords: Somatosensory cortex ; Interlaminar ; Corticortical ; SI ; Area 3b ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The morphology of single neurons in area 3b of cat primary somatosensory (SI) cortex was examined after horseradish peroxidase (HRP) injections. Neurons were labeled either by intracellular injection of HRP following intracellular recording or by small extracellular iontophoretic HRP injections. Both pyramidal and nonpyramidal neurons were labeled and reconstructed from serial sections. Their axons had local, interlaminar and interareal patterns of termination. Most neurons formed local axonal fields around their cell bodies and dendrites. Pyramidal neurons in cortical layer IV sent axons up into layers II and III, neurons in layers II and III sent axons down to layer V, and layer V neurons sent axons to layer VI as well as back to the upper layers. Layer VI neurons sent axons back to the upper cortical layers in a unique bowl-shaped pattern. The horizontal distribution of axons of pyramidal cells in layer III was extremely widespread. Axons of layer III neurons in area 3b terminated within 3b and area 1, but not in other areas of SI. Layer III neurons in area 1 distributed axon collaterals to all fields of SI as well as projecting a main axon to motor cortex. In general, the axon collaterals of area 3b pyramidal cells outside layer III remained confined to area 3b. Most of the nonpyramidal neurons labeled were basket cells in layers III and VI. These neurons formed dense axonal fields around their cell bodies, and none of their axons could be followed into the underlying white matter. The results of the present study demonstrate that area 3b somatosensory cortical neurons and their axons are vertically organized in a manner similar to that reported for other sensory cortical areas. They also show that widespread horizontal connections are formed by pyramidal neurons of layer III, and that these horizontal axons can travel for great distances in the cortical grey matter.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00230238
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  • 22
    Electronic Resource
    Electronic Resource
    Excitatory interactions between phrenic motoneurons: intracellular study in the cat (1989)
    Springer
    Experimental brain research 74 (1989), S. 131-138 
    Details
    ISSN: 1432-1106
    Keywords: Phrenic motoneurons ; Intracellular recording ; Interactions ; Recurrent EPSPs ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary 1. Intracellular recordings were made from 220 Phrenic Motoneurons (PM) in anaesthetized, spontaneously breathing cats, deafferented from C3 to C7, in order to look for somatic events related to the Recurrent Responses (RR) evoked in PM axons by repetitive stimulation of the phrenic nerve. RR appear sporadically at a constant latency, originate from a spinal nicotinic mechanism and can be evoked in a PM without the presence of an antidromic volley in its axon (Khatib et al. 1986). 2. Using stimuli effective for eliciting RR in axons, we failed to observe intracellularly somatic events corresponding to RR after the occurence of an antidromic action potential. RR were observed extracellularly in two cases, but in both cases the recording originated from axons. 3. We attempted to elicit somatic RR without a preceding antidromic action potential, using either parathreshold stimulation of the impaled PM, or suprathreshold stimulation of a phrenic strand which excluded the axon of the impaled PM. In both cases, RR-like events, with very stable latencies, appeared sporadically in 4/142 and 2/15 PMs respectively. 4. Parathreshold stimuli or stimulation of a strand were coupled with averaging of the synaptic noise in order to look for small events temporally related to the stimuli. Short latency small depolarizations, looking-like recurrent EPSPs, were revealed in 22/142 and 5/15 PMs respectively. 5. These results confirm the existence of interrelations between PMs, providing for re-excitation and coupling within the phrenic pool, in addition to centrally imposed synchronization.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00248286
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  • 23
    Electronic Resource
    Electronic Resource
    Binocular depth perception, visual acuity and visual fields in cats following neonatal section of the optic chiasm (1989)
    Springer
    Experimental brain research 74 (1989), S. 272-278 
    Details
    ISSN: 1432-1106
    Keywords: Cat ; Corpus callosum ; Optic chiasm ; Stereoacuity ; Visual acuity ; Visual fields
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary We studied the role of the transcallosal pathway in stereopsis by measuring binocular and monocular depth perception in two cats that had undergone section of the optic chiasm at the age of 21 d. To ensure that the surgery did not impair vision to the extent that depth perception could not be evaluated, visual acuity and visual fields were also measured. In both of the chiasm-sectioned animals the visual fields were reduced and the visual acuity was substantially lower than in normal cats, with a maximum of about 2 cyc deg-1. Binocular depth thresholds of the chiasm-sectioned cats were worse than those of the normal cat but were better than their own monocular thresholds. These results suggest that the chiasm-sectioned animals were still able to use binocular cues to judge depth and indicate that the indirect pathway through the corpus callosum is sufficient to mediate binocular depth perception.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00248860
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  • 24
    Electronic Resource
    Electronic Resource
    Demonstration of axonal branching of fibres from certain precerebellar nuclei to the cerebellar cortex and nuclei: a retrograde fluorescent double-labelling study in the cat (1989)
    Springer
    Experimental brain research 75 (1989), S. 15-27 
    Details
    ISSN: 1432-1106
    Keywords: Precerebellar nuclei ; Cerebellar cortex and nuclei ; Fluoro-Gold ; Rhodamine-B-isothiocyanate (RITC) ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The projections from certain brain stem precerebellar nuclei to the cerebellar cortex and nuclei have been examined in the cat by using the retrograde fluorescent double-labelling technique. Crystalline Fluoro-Gold was implanted into the left cerebellar nuclei from the contralateral side and rhodamine-B-isothiocyanate was injected into the overlying cerebellar cortex. The inferior olive, the lateral reticular nucleus, and the reticular tegmental pontine nucleus all contained double- as well as single-labelled neurons, and it was concluded that these nuclei have a high number of neurons whose axons branch to both the cerebellar cortex and nuclei. The neurons in the paramedian reticular nucleus and the pontine nuclei proper appear to project only to the cerebellar cortex.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00248525
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  • 25
    Electronic Resource
    Electronic Resource
    Projections from the rostral mesencephalic reticular formation to the spinal cord (1989)
    Springer
    Experimental brain research 75 (1989), S. 265-279 
    Details
    ISSN: 1432-1106
    Keywords: Rostral interstitial nucleus of the MLF ; Interstitial nucleus of Cajal ; Spinal cord ; Motoneurons ; Neck muscles ; Axial muscles ; Vertical eye and head movements ; Autoradiography ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Eye and head movements are strongly interconnected, because they both play an important role in accurately determining the direction of the visual field. The rostral brainstem includes two areas which contain neurons that participate in the control of both movement and position of the head and eyes. These regions are the caudal third of Field H of Forel, including the rostral interstitial nucleus of the medial longitudinal fasciculus (riMLF) and the interstitial nucleus of Cajal with adjacent reticular formation (INC-RF). Lesions in the caudal Field H of Forel in monkey and man result in vertical gaze paralysis. Head tilt to the opposite side and inability to maintain vertical eye position follow lesions in the INC-RF in cat and monkey. Projections from these areas to extraocular motoneurons has previously been observed. We reported a study of the location of neurons in Field H of Forel and INC-RF that project to spinal cord in cat. The distribution of these fiber projections to the spinal cord are described. The results indicate that: 1. Unlike the neurons projecting to the extra-ocular muscle motoneurons, the major portion of the spinally projecting neurons are not located in the riMLF or INC proper but in adjacent areas, i.e. the ventral and lateral parts of the caudal third of the Field H of Forel and in the INCRF. A few neurons were also found in the nucleus of the posterior commissure and ventrally adjoining reticular formation. 2. Neurons in caudal Field H of Forel project, via the ventral part of the ventral funiculus, to the lateral part of the upper cervical ventral horn. This area includes the laterally located motoneuronal cell groups, innervating cleidomastoid, clavotrapezius and splenius motoneurons. At lower cervical levels labeled fibers are distributed to the medial part of the ventral horn. Projections from the caudal Field H of Forel to thoracic or more caudal spinal levels are sparse. 3. Neurons in the INC-RF, together with a few neurons in the area of the nucleus of the posterior commissure, project bilaterally to the medial part of the upper cervical ventral horn, via the dorsal part of the ventral funiculus. This area includes motoneurons innervating prevertebral flexor muscles and some of the motoneurons of the biventer cervicis and complexus muscles. Further caudally, labeled fibers are distributed to the medial part of the ventral horn (laminae VIII and adjoining VII) similar to the projections of Field H of Forel. A few INC-RF projections were observed to low thoracic and lumbosacral levels. It is argued that the neurons in the caudal Field H of Forel, which project to the spinal cord are especially involved in the control of those fast vertical head movements which occur in conjunction with saccadic eye movements. In contrast the INC-RF projections to the spinal cord are responsible for slower, smaller movements controlling the position of the head in the vertical plane.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00247933
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  • 26
    Electronic Resource
    Electronic Resource
    Axis of preferred motion is a function of bar length in visual cortical receptive fields (1989)
    Springer
    Experimental brain research 76 (1989), S. 307-314 
    Details
    ISSN: 1432-1106
    Keywords: Moving stimuli ; Orientation specificity ; Preferred axes ; Spot-response-axis ; Striate cortex ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The responses of 82 simple cells and 41 complex cells in area 17 of anesthetized and paralysed cats were examined with light bars of different length. For 84% of the simple cells and 66% of the complex cells the preferred axis of orientation of a stationary flashing long bar (orientational selectivity) and the preferred axis of movement of a small spot were parallel. As a consequence, the axis of maximal response to a moving light spot was mostly orthogonal to the optimal axis of a moving bar. Thus, a single cell responds to two perpendicular axes of preferred movement one for a long bar and one for a light spot, respectively. For both axes independent direction preferences could be distinguished. Additional preferred axes of movement between the two orthogonal extremes could be found with moving bars of intermediate lengths. This can be explained by the fact that cells with a pronounced response to a moving spot showed a strong tendency for intermediate bar length to elicit responses consisting of a superposition of both components. Therefore, decreasing bar length resulted in a gradual rotation of the preferred direction of movement from orthogonal to parallel with respect to the orientational axis, rather than to a mere widening of the tuning curve. Accordingly, the change in orientation selectivity with decreasing bar length is a regular transition from the orientation dependent response to a response type that depends only on the movement axis of the spot. Thus, in a simple model, the resulting response characteristic can be interpreted as an average of both components weighted according to the length of the stimulus.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00247890
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  • 27
    Electronic Resource
    Electronic Resource
    Cat red nucleus activity preceding movement depends on initiation conditions (1989)
    Springer
    Experimental brain research 77 (1989), S. 271-282 
    Details
    ISSN: 1432-1106
    Keywords: Red nucleus ; Motor initiation ; Single-unit activity ; Reaction time ; Delayed movement ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The activity of 98 Red Nucleus neurons was recorded in 3 cats operantly conditioned to perform a ballistic forelimb flexion movement triggered after a brief sound in a simple Reaction Time condition, or Delayed after the same sound in the presence of a tone cue. Fifty-eight task related neurons presented changes of activity in either one or both conditions. Forty-four of them were studied quantitatively and classified in 3 categories: 1) only 16% of the units presented similar changes of firing preceding the triggered or delayed movement; 2) most units (55%) presented different changes of activity in the two conditions: in the Delayed condition, the activation occurred earlier before the movement, and/or the change in magnitude was reduced or the pattern of activity was modified; 3) moreover, for 29% of the units, the change of activity observed before movement in the Reaction Time condition was severely reduced or even absent in the Delayed condition. For some of these neurons a building-up of activity was observed very early in the Reaction Time condition, during the preparatory period, well before the occurrence of the conditioned stimulus. These results show that the Red Nucleus activity preceding a movement is clearly dependent on its initiation conditions. The distinct patterns of unit firing observed in the Reaction Time condition and in the Delayed condition are tentatively related to the different preparation and initiation constraints determined by the behavioral conditions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00274984
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  • 28
    Electronic Resource
    Electronic Resource
    Actions of excitatory amino acid antagonists on synaptic potentials of layer II/III neurons of the cat's visual cortex (1989)
    Springer
    Experimental brain research 78 (1989), S. 489-500 
    Details
    ISSN: 1432-1106
    Keywords: NMDA receptor ; Visual cortex ; Excitatory amino acid ; Slice ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Actions of excitatory amino acid (EAA) antagonists on the responses of cells in layers II/III and IV of the cat's visual cortex to stimulation of layer VI and the underlying white matter were studied in slice preparations. Antagonists used were 2-amino-5-phosphonovalerate (APV), a selective antagonist for the N-methyl-D-aspartate (NMDA) type of EAA receptors, and kynurenate, a broadspectrum antagonist for the three types of EAA receptors. In extracellular recordings it was demonstrated that most of the layer II/III cells were sensitive to APV, while the great majority of the layer IV cells were not, By contrast, kynurenate suppressed the responses completely in both layers. Excitatory post-synaptic potentials (EPSPs) evoked by stimulation of layer VI and the while matter were recorded intracellularly from layer II/III neurons. To determine whether the EPSPs were elicited mono- or polysynaptically, the synaptic delay for each EPSP was calculated from a pair of onset latencies of EPSPs evoked by stimulation of the two sites. Forty-two percent of the layer II/III cells were classified as having monosynaptic EPSPs. In 60% of these monosynaptic cells, the rising slope of the EPSPs was reduced by APV while in the other 40%, it was not. In the former (APV-sensitive cells), subtraction of the APV-sensitive component from the total EPSP indicated that the onset latency of the NMDA receptor-mediated component was roughly equal to that of the non-NMDA component. In the latter (APV-resistant cells), only the slowly-decaying component was in part mediated by NMDA receptors. The conduction velocities of the afferent fibers innervating APV-resistant cells were slower than those of the APV-sensitive cells, suggesting that both types of cells are innervated by different types of afferents. The polysynaptic EPSPs of almost all layer II/III cells were sensitive to APV. The subtraction method indicated that the NMDA component had about the same magnitude as the non-NMDA components. When the slices were superfused by a Mg2+-free solution, the EPSPs were potentiated dramatically, but this potentiation was reduced to the control level during the administration of APV. Similarly, APV-sensitive components were potentiated during the administration of bicuculline, a selective antagonist for gamma-aminobutyric acid receptors of A type. These results suggest that NMDA receptors participate, at varying degrees, in excitatory synaptic transmission at most layer II/III cells in the cat's visual cortex, and their actions appear to be regulated by intracortical inhibition.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00230237
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  • 29
    Electronic Resource
    Electronic Resource
    Effects of dark rearing on the development of visual callosal connections (1989)
    Springer
    Experimental brain research 78 (1989), S. 203-213 
    Details
    ISSN: 1432-1106
    Keywords: Corpus callosum ; Development ; Vision ; Dark rearing ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary It is now well established that during normal postnatal development there is a partial elimination of the callosal projections of cortical areas 17 and 18 in the cat and that visual experience early in life can modulate this process. In the present experiments, we quantitatively studied the influence of light, per se, by rearing cats in total darkness. Dark rearing exaggerates the normally occurring partial elimination of immature callosal projections: it causes a significant reduction in the total number of neurons in both the supra-and infragranular layers that send an axon through the corpus callosum and slightly narrows the distribution of these neurons across areas 17 and 18. These data demonstrate that visual stimulation is not necessary either to initiate the partial elimination of immature callosal projections or to stabilize a large fraction of the callosal projections present at birth. However, normal visual stimulation is necessary for the stabilization of the normal complement of callosal projections.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00230700
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  • 30
    Electronic Resource
    Electronic Resource
    Role of the sensorimotor cortex in postural adjustments accompanying a conditioned paw lift in the standing cat (1989)
    Springer
    Experimental brain research 78 (1989), S. 588-596 
    Details
    ISSN: 1432-1106
    Keywords: Motor cortex ; Conditioned movement ; Posture ; Balance control ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The role of the sensorimotor cortex in the postural adjustments associated with conditioned paw lifting movements was investigated in the cat. Cats were trained to stand quietly on four strain gauge equipped platforms and to perform a lift-off movement with one forelimb when a conditioned tone was presented. The parameters recorded were the vertical forces exerted by the paws on each platform, the lateral and antero-posterior displacements of rods implanted on the T2, T12, L5 vertebrae as well as their rotation, and the EMG of triceps and biceps of both forelimbs. Before lesion, the postural adjustment consisted of a “nondiagonal” pattern where the CG was displaced laterally inside the triangle formed by the three remaining supporting limbs. Here a lateral bending of the thoracic column toward the supporting forelimb could be observed. The associated EMG pattern consisted of an early activation of the triceps lateral head in the moving limb which was probably responsible for the body displacement toward the opposite side, and a late biceps activation associated with the lift. In the supporting forelimb, a coactivation of the biceps and triceps was usually present. After contralateral sensorimotor lesion, the conditioned lifting movements were lost for 4–15 days after the lesion, before being subsequently recovered. The same lateral CG displacement and bending of the back was seen after lesion as before, which indicates that the goal of postural adjustment was preserved. However, the means of reaching it were modified. In most of the intact animals, the CG displacement was achieved in one step, whereas in the animals with lesions, the displacement was made either according to a slow ramp mode or in a discontinuous manner involving several steps. The mechanisms responsible for this disturbance are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00230246
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    Electronic Resource
    Electronic Resource
    Cytochemical studies of normal feline blood and bone marrow cells (1989)
    Springer
    Annals of hematology 58 (1989), S. 195-199 
    Details
    ISSN: 1432-0584
    Keywords: Cytochemistry ; Blood ; Bone marrow ; Leukocytes ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Blood and bone marrow cells of ten clinically healthy cats were stained for alkaline phosphatase (ALP), peroxidase (PO), chloroacetate esterase (CAE), alpha-naphthyl butyrate esterase (NBE), sudanophilia, and periodic acid-Schiff (PAS) reaction. Mature neutrophils in blood and bone marrow were devoid of ALP and NBE, but exhibited modest to strong PO, CAE, sudanophilia, and PAS reaction. In bone marrow, sudanophilia, PO, and CAE were prominent at the promyelocyte stage and diminished with cellular differentiation and maturation, while PAS reactivity increased with cell maturation usually from the myelocyte stage onwards. Myeloblasts were negative for all cytochemical reactions, but some large unidentifiable cells reacted strongly for ALP. Eosinophils were slightly reactive for ALP, CAE, and PAS, but not for PO, sudanophilia, and NBE. Basophil granules stained strongly for CAE, revealed PAS positivity, and stained negatively for PO, NBE, ALP, and sudanophilia. Slight ALP activity was detected in the intergranular cytoplasm of basophils. Lymphocytes and monocytes, with few exceptions, stained negatively. An occasional lymphocyte revealed slight globular NBE activity (NaF-resistant) and diffuse PAS reaction, while an occasional monocyte contained a few PO-positive and sudanophilic granules. Monocytes reacted modestly, whereas bone marrow macrophages reacted strongly for NBE (NaF-sensitive). Cells of the erythroid series stained negatively for all cytochemical reactions, megakaryocytes were PAS-positive, and platelets gave positive reactions for PAS and CAE.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00320772
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  • 32
    Electronic Resource
    Electronic Resource
    Feline sporotrichosis: A case report (1989)
    Springer
    Mycopathologia 108 (1989), S. 149-154 
    Details
    ISSN: 1573-0832
    Keywords: Sporotrichosis ; Sporothrix schenckii ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract The isolation of Sporothrix schenckii from a female European cat it is described. The cat showed lengthened alopecic areas, with prominent nodules in the external surface of the thighs and abdomen. A mycological and histopathological studies of the lesions were carried out. The lesions resolved under treatment with 20% potassium iodide in doses of 0'1 ml/kg oral route in a 8 weeks period.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00436219
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  • 33
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    Electronic Resource
    Relative rates of bromination and chlorination of 4-substituted cyclopentenes in methanol, ethanol and acetic acid (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 26-34 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: A set of 4-monosubstituted cyclopentenes, , were synthesized and their relative rates (kX/kH) for bromination and chlorination were determined in methanol, ethanol and acetic acid at 25 °C by competitive method. log(kX/kH) for most of the substituents can be correlated by means of Taft's equation, log(kX/kH) = ρI σI + C. In methanol ρI, Br2 = -2·91, ρI, Cl2 = -0·49, in ethanol ρI, Br2 = -3·07, ρI, Cl2 = -0·70 and in acetic acid ρI, Br2 = -1·64, ρI, Cl2 = -0·65. The presence of C(〈0) is due to a constant steric effect. The deviation of X = H is ascribed to the absence of the steric effect and that of X = CO2Me and CO2Et is accounted for in terms of anchimeric assistance. For chlorination no anchimeric assistance was observed.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020104
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  • 34
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    Electronic Resource
    The cation radical vinylcyclobutane rearrangement (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 57-88 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The cation radical vinylcyclobutane (VCB) rearrangement is found to be a reaction of substantial scope, synthetic utility, and exceptional kinetic facility. In conjuction with cation radical cyclobutanation, it constitutes an effective method for net (indirect) Diels-Alder addition to electron rich dienophiles. Reactions can be carried out with either aminium salt or photosensitized electron transfer (PET) initiation and are powerfully facilitated by ionizable substituents such as p-anisyl, phenylthio, and phenoxy at the 2-position of the vinylcyclobutane. The intramolecularity of the reaction is clearly established and in four discrete systems preferred sr (suprafacial/retention) stereochemistry is observed. A theoretical basis for sr stereochemistry in the cation radical VCB rearrangement is advanced. The transition state for the reaction is considered to be similar to that for the direct cation radical Diels-Alder cycloaddition, another cation radical pericyclic reaction which converges on the same product. This model of the VCB rearrangement transition state is used to rationalize the strong rate-retarding effect of a Z-methyl substituent attached to the vinyl group and of a methyl substituent at the 4-position of the vinylcyclobutane ring cis to the vinyl substituent.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020108
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    The ‘dimer mechanism’ in aromatic nucleophilic substitution by amines in aprotic solvents (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 1-14 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The mechanism of aromatic nucleophilic substitutions by amines in protic solvents is well established; on the contrary the mechanism/s of the reactions in aprotic solvents is/are still subject of controversy. The present paper describes several systems for which fourth-order kinetics (third-order in amine) were observed. A mechanism is proposed to account for this as well as other observation such as: overall negative energies of activation, quadratic dependence of kA with non-nucleophilic tertiary bases, spectacular effects of hydrogen-bond donor (HBD) and hydrogen-bond acceptor (HBA) catalysts, etc. Other alternative mechanisms are also discussed.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020102
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    Cross interaction constants as a measure of the transition state structure (part III). Mechanism of reactions between 1-phenylethyl benzenesulfonates with N,N-dimethylanilines (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 35-42 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The kinetics and mechanisms of the reactions between 1-phenylethyl benzenesulfonates (1-PEB) with N,N-dimethylanilines are investigated in methanol at 35·0°C. Reactivity and selectivity trends were found to be similar to those for the reactions of 1-PEB with anilines, but the magnitudes of cross interaction constants, ρXZ, between substituents X in the nucleophile and Z in the leaving group were substantially smaller indicating no hydrogen-bond bypass bridge formation in the transition state. However, the magnitude of ρXZ suggested a direct electrostatic interaction between the reaction centers in the nucleophile and leaving group in the frontside nucleophilic attack with a loose transition state structure.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020105
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    Reassignment of the fundamental vibrations of azetidine from ab initio calculations (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 183-186 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The harmonic vibrational frequencies were calculated analytically at the 6-31** level for azetidine using the GAUSSIAN 82 program. The results strongly indicate the presence of several errors in a recent assignment of the fundamentals of azetidine based on a normal coordinate analysis and a revised assignment is suggested. It is concluded that reliable vibrational data for azetidine in the gas phase are needed in order to resolve the remaining ambiguities in the interpretation of the spectra.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020210
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    Electronic Resource
    Masthead (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989) 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020201
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  • 39
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    Multifunctional catalysis for transamination reaction of α-amino acids with glyoxylic acid in synthetic bilayer memberane (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 110-116 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The transamination reaction of α-amino acids with glyoxylic acid as catalyzed by copper(II) ions was investigated kinetically in an aqueous medium at pH 5·0 and 30·0°C. L-Phenylalanine transferred its amino group to glyoxylic acid most readily among seven different amino acids used here in the single-walled bilayer vesicle formed with N,N-dihexadecyl-Nα-[6-(trimethylammonio)hexanoyl]-L-histidinamide bromide (N+C5His2C16). Such rate enhancement was found to originate from the cooperative trifunctional catalysis: a coordination effect exercised by copper(II) ions, a general acid-base catalysis by the imidazolyl group of the lipid, and a hydrophobic field effect provided by the bilayer vesicle. Lack of any of the three functions failed to give out significant rate enhancement. As regards correlation between the reactivity and the nature of α-amino acids, the copper(II)-catalyzed transamination was progressively enhanced as hydrophobicity of the α-amino acid was increased in the N+C5His2C16 vesicle.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020204
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  • 40
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    Electronic Resource
    Kinetics and mechanism of the acid-catalyzed hydration of dihydro-1,4-dioxin (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 43-50 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The cyclic vinyl ether dihydro-1,4-dioxin is converted to its cyclic hemiacetal hydration product, 2-hydroxy-1,4-dioxane, in aqueous solution by an acid-catalyzed reaction for which kH+ = 1·80 × 10-5 M-1 S-1 at 25°C. This reactivity and the solvent isotope effect kH+/kD+ = 2·2 show that the reaction occurs by rate-determining proton transfer from catalyst to substrate and not by a pre-equilibrium mechanism as recently proposed.2
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020106
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  • 41
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    Theoretical studies of the singlet and triplet potential energy surfaces of cyclobutanediyl (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 161-176 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Cyclobutanediyl (2) has been studied in both its singlet and triplet states by ab initio electronic structure theory. The triplet, which is the ground state of the molecule, exists in both C2h and C2v forms which interconvert via a Cs transition state. For the singlet, only a C2h form is found. It passes, via a Cs transition state, onto the C2v surface on which bicyclobutane (3) is the only minimum. The ring-flipping (inversion) process in 3 includes the singlet biradical as an intermediate, and involves a novel, non-least motion path similar to one previously proposed by Gassman. Semiclassical periodic orbit theory indicates that the various minima on both the singlet and triplet surfaces can interconvert via quantum mechanical tunneling.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020208
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  • 42
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    Twisted internal charge transfer emission in B,B-bis(mesityl) pyrroloboranes (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 89-92 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Spectral characteristics of several simple substituted B,B-bis(mesityl)pyrroloboranes are reported which support a theoretical treatment by Bonacic-Koutecky and Michl (J. Am. Chem. Soc. 107, 1765 (1985)) describing the excited states of simple aminoboranes as an example of twisted internal charge transfer. In the aminoboranes the pyrrolo moiety functions as the electron donor group and the empty p-orbital of the boron atom as the acceptor.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020109
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  • 43
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    A preliminary quantum-chemical study of the mechanisms for the reactions of perchlorofluoroethanes with nucleophiles initiated by chlorophilic attacks (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 103-109 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: A preliminary theoretical study of the mechanisms for the reactions of the perchlorofluoroethanes CF2ClCCl3 (1), CF2ClCCl2F (2) and CF3CCl3 (3), with nucleophiles has been carried out by the MNDO method, following the experimentally suggested process shown in Scheme 1. The unlikely chlorophilic attack in the first step of Scheme 1 has been shown to be feasible for 1, 2 and 3 by analysis of the MO interactions. The second step has been found to be affected by the anionic hyperconjugation which stabilizes the anions CF2ClCCl2- (4), CF2ClCClF- (5) and CF3CCl2- (6) and would make reactions (2) (the second step) unfeasible in gas phase, but in solution reaction (2) may still easily occur for 4 and 5.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020203
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  • 44
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    Studies on organophosphorus compounds XXXII. A molecular mechanics study of the hydrolytic reaction of alkylphosphonates and alkylphosphonyl chlorides (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 146-160 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The alkaline hydrolysis of several alkylphosphonates and alkylphosphonyl chlorides has been investigated by molecular mechanics calculations (MM2, 1985 version). The difference of the steric energies (ΔE) between tetracoordinate substrate and pentacoordinate transition state of phosphorus compounds represents the activation energy (ΔE≠) in hydrolysis. The change of ΔE for various alkyl groups relative to methyl group (ΔΔER) is suggested as a measure of the steric effect of substituents. Thus the correlation analysis involving log k and ΔΔER of the branched alkyl group gives good results and it is reasonable to anticipate that analogous treatment using ΔΔER for the straight chain alkyl group is not satisfactory owing to the minor contribution of steric effect of the latter. However, the multiple regression analysis of log k with ΔΔER and Taft's σ* provides very good results. As shown by us, for the hydrolytic reactions studied, the proposed ΔΔER is much better than Taft's Es and Charton's ν, the commonly used well-known steric parameters in the chemistry of carbon compounds.
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020207
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  • 45
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    Mechanism of the Grignard reaction (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 205-213 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Mechanism of the Grignard reactions of aromatic ketones in THF was studied by spectroscopic and kinetic methods. The stable radical intermediates generated in the initial electron transfer from Grignard reagent to ketones are in a state of aggregated dimer of corresponding ion-radical pairs; in which two ketone anion radicals are bridged by a dimer di-cation of Grignard reagent. Subsequent alkyl radical transfer from dimeric Grignard reagent cation moiety to ketone anion radical aggregated each other are promoted by a participation of another neutral Grignard reagent. Proposed mechanism by present authors is able to explain well addition products/reduction products ratios in the Grignard reactions.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020303
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  • 46
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    Electronic Resource
    Non-hierarchical classification of organic solvents using characteristic vector analysis of physical and empirical solvent parameters (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 232-242 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Characteristic vector analysis of a set of six physical and empirical parameters of 103 commonly used organic solvents (bp, ∊r, μ, nD, ETN, and δ) gives four vectors describing 95% of the total data variability. Non-hierarchical cluster analysis, applied to our results, leads to ten separate classes of organic solvents.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020306
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  • 47
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    Electronic Resource
    Masthead (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989) 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610020101
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  • 48
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    Ion pairs in solvolysis reactions. Kinetic deuterium isotope effects for deprotonation of carbocation intermediates in aqueous solvent (1989)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 15-25 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Solvolysis of 2-X-2-phenylpropane (1-X) in 25 vol% acetonitrile in water at 25°C produces 2-hydroxy-2-phenylpropane (1-OH) and 2-phenylpropene (3). The carbocationic intermediate discriminates between different nucleophiles; azide anion, acetate anion, and methanol are more efficient nucleophiles than water, kN3/kH2O = 42 kOAc/kH2O = 3, and kMeOH/kH2O = 2·9 (ratio of second-order rate constants). The fraction of the elimination product 3 increases with increasing basicity of the leaving group X as well as by addition of general bases. The Brønsted parameter for this catalysis is small, β = 0·13, with substituted acetate anions. The kinetic deuterium isotope effect for the dehydronation of the intermediate has been measured (assuming the reaction from intermediate to alcohol is insensitive to isotopic substitution) employing the hexadeuterated substrate d6-1-X as k3H/k3d6 = 3·5 ± 0·2 for the chloride 1-Cl with acetate anion, and, without added base, 3·1 ± 0·2 for the acetate 1-OAc, and 3·1 ± 0·2 for the p-nitrobnzoate 1-PNB, respectively, and ∼5 for the protonated methyl ether 1-OMeH+. The variation in isotope effect with change in leaving group is discussed in terms of elimination from contact ion pairs and ‘free’ carbocation. The overall kinetic isotope effect for the solvolysis was found to be kobsH/kobsd6 = 1·31 (1-OMeH+), 1·38 (1-OAc), 1·40 (1-PNB), and 5·7 (1-OH2+). These isotope effects consist of the isotope effect k12H/k12d6 for the formation of the substitution product 1-OH and k13H/k13d6 for production of the olefin 3. It is concluded that the latter isotope effect is enlarged owing to a branched mechanism in which the deprotonation of the carbocationic intermediate competes with formation of the substitution product. As large an isotope effect as k13H/k13d6 ∼6·5 has been measured for 1-OMeH+.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/poc.610020103
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  • 49
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    Implications of chirality and geometric isomerism in some psychoactive drugs and their metabolites (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 99-120 
    Details
    ISSN: 0899-0042
    Keywords: asymmetry ; enantiomers ; geometric isomers ; (+)- (-)-isomers ; D- and L-isomers ; R- and S-isomers ; Z- and E-isomers ; drug metabolism ; stereoselectivity and stereospecificity in drug action ; stereoselectivity and stereospecificity in drug metabolism ; psychotropic drugs ; stimulants ; antidepressants ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Many drugs contain a chiral centre, or such a centre is introduced during metabolism of the drug in man and in animals. If a single chiral centre is present, the drug will normally exist as a mixture of two enantiomers, of which one may have quite different pharmacologic and/or toxic effects than the other. Chiral drugs that are used in psychiatry, and some other pharmacologically related drugs are identified, and the implications of the presence of one or two chiral centres in these drugs are discussed. Differences in pharmacologic properties of drug and metabolite enantiomers are identified and discussed. Also reviewed are the properties of some drugs used in psychiatry that both are chiral and display geometric isomerism.
    Additional Material: 3 Tab.
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    URL: http://dx.doi.org/10.1002/chir.530010204
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  • 50
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    Pharmacokinetic data of propranolol enantiomers in a comparative human study with (S)- and (R,S)-propranolol (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 10-13 
    Details
    ISSN: 0899-0042
    Keywords: (S)-, (R,S)-propranolol ; pharmacokinetic ; human study ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The pharmacokinetics of (S)-propranolol were compared after the oral administration of a 40 mg dose of the pure enantiomer and an 80 mg dose of a racemic mixture of (R,S)-propranolol. The results of this study indicate that the bioavailability of (S)-propranolol, as expressed by the mean area uner the concentration-time curve (AUC) and maximum serum concentration, is lower after 40mg of the optically pure drug than after the racemic drug.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010105
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  • 51
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    Masthead (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989) 
    Details
    ISSN: 0899-0042
    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/chir.530010301
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  • 52
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    Stereochemistry of tissue distribution of racemic propranolol in the dog (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 192-196 
    Details
    ISSN: 0899-0042
    Keywords: propranolol enantiomers ; enantiomers ; propranolol ; β-receptor-blocking drugs ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Only limited information is available on the stereochemistry of the in vivo distribution of β-receptor-blocking drugs. In this study we determined the levels of the propranolol enantiomers in plasma, cerebrospinal fluid (CSF) and central nervous system (CNS), and peripheral tissues in the dog following an intravenous dose of a deuterium-labeled pseudoracemate. The appearance of the propranolol enantiomers in the CSF was rapid and nonstereoselective, with maximum concentrations reached at 15 min after dosing. The levels of the enantiomers in both CSF and plasma then declined in a parallel biphasic fashion, with a terminal t1/2 of about 125 min. Except for an early high CSF/plasma concentration ratio of 0.35, the CSF propranolol levels corresponded to the unbound concentration in plasma, CSF/plasma 0.20. All areas of the brain showed a similar uptake of propranolol, with a tissue concentration exceeding that in plasma about 10-fold during the terminal phase of elimination. The uptake of propranolol by peripheral tissues varied widely, ranging from a 50-fold accumulation by the lungs compared to plasma to no accumulation by adipose tissue. However, as for the CSF, there was no evidence of stereoselective uptake of propranolol by any CNS or peripheral tissue except for the liver. A significantly higher level of (+)- vs. (-)-propranolol in liver tissue presumably was a reflection of stereoselective hepatic metabolism of (-)-propranolol by this tissue. The slight stereoselectivity in plasma binding of propranolol known to exist in the dog had no significant influence on tissue or CSF distribution.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010303
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  • 53
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    Separation and quantitation of (R)- and (S)-atenolol in human plasma and urine using an α1-AGP column (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 209-215 
    Details
    ISSN: 0899-0042
    Keywords: enantiomeric separation ; bioanalysis ; α1-acid glycoprotein column ; disposition (R)- and (S)-atenolol ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A method for the determination of (R)- and (S)-atenolol in human plasma and urine is described. The enantiomers of atenolol are extracted into dichloromethane containing 3% heptafluorobutanol followed by acetylation with acetic anhydride at 60°C for 2 h. The acetylated enantiomers were separated on a chiral α1-AGP column. Quantitation was performed using fluorescence detection. A phosphate buffer pH 7.1 (0.01 M phosphate) containing 0.25% (v/v) acetonitrile was used as mobile phase. The described procedure allows the detection of less than 6 ng of each enantiomer in 1 ml plasma. The relative standard deviation is 4.4% at 30 ng/ml of each enantiomer in plasma. The plasma concentration of (R)- and (S)- atenolol did not differ significantly in two subjects who received a single tablet of racemic atenolol. The R/S ratio of atenolol in urine was ∼ 1.
    Additional Material: 7 Ill.
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  • 54
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    First announcement and call for papers (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 246-248 
    Details
    ISSN: 0899-0042
    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/chir.530010312
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  • 55
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    Improved performance of the second generation α1-AGP columns: Applications to the routine assay of plasma levels of alfuzosin hydrochloride (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 243-245 
    Details
    ISSN: 0899-0042
    Keywords: stereochemistry ; enantiomers ; direct separation ; alfuzosin ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Described is a direct enantioselective separation of the enantiomers of alfuzosin hydrochloride on the second generation α1-AGP column which offers improved efficiency, shorter analysis, and improved stability with respect to the first generation columns. The method has been applied to the analysis of drug substance in rat plasma. This highly efficient extraction method and the use of fluorimetric detection result in selective and sensitive determination of the enantiomers. The analytical validation parameters demonstrate the applicability of this method to pharmacokinetic and metabolic studies.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010311
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  • 56
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    Polarimetric detection in high-performance liquid chromatography (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 251-264 
    Details
    ISSN: 0899-0042
    Keywords: optical activity ; optical rotation ; chiroptical detection ; enantiomeric purity ; chiral separation ; enantioselective reactions ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chiroptical detection for HPLC is particularly useful as a selective detection method for chiral molecules, and in enantiomeric purity determination with partial chiral separation or without chiral separation. The recent development of laser-based polarimeters with microdegree sensitivity has increased the applicability of optical rotation detection in HPLC. The detection limit of these instruments is submicrogram on-column for many chiral compounds in analytical HPLC. A variety of applications of the selective detection of optically active molecules are reviewed. The use of polarimetric detection with partial chiral separation is considered, both as an aid to method development and for enantiomeric purity determination. Finally applications to enantiomeric purity determination without chiral separation are reviewed, with the dual use of nonchirally selective and chiroptical detectors to determine the total amount and optical purity of the analyte. Determinations of chiral purity for samples of high enantiomeric excess are described, which with laser-based instrumentation may give accuracies of better than ± 1% with sample loadings of 50 μg on an achiral column. Applications to the study of enantioselective reactions are also considered, with determination of enantiomeric excess in near-racemates to better than ± 0.1%.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010403
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    The role of configuration and conformation in the binding of 2,3-benzodiazepines to human serum albumin (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 271-275 
    Details
    ISSN: 0899-0042
    Keywords: HSA-affinity chromatography ; interconverting conformers ; conformational selectivity ; conformational diastereomers ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2,3-Benzodiazepines containing a centre of asymmetry at C-5 possess both central and helical chiralities, and the solution of their racemates contains four molecular species. The binding of these compounds to human serum albumin (HSA) was studied by affinity chromatography. The binding strength depended both on the steric orientation of the 5-ethyl substituent and on the conformation of the diazepine ring. Conformation P (defined by the positive sign of C-1-N-2-N-3-C-4 torsion angle) is favoured, while the quasiaxial orientation -of the 5-ethyl substituent is not favoured by the albumin molecule.
    Additional Material: 4 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010405
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    Stereoisomeric flavour compounds XXXV: Chiral aroma compounds of sherry I. Optically pure stereoisomers of solerone and solerole (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 293-300 
    Details
    ISSN: 0899-0042
    Keywords: optical isomers ; chirality and odour ; chiral flavour compound resolution ; enantiomer separation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantioseparation of the sherry aroma components 5-oxo-4-hydroxyhexanoic acid γ-lactone (solerone) and 4,5-dihydroxyhexanoic acid γ-lactone (solerole) is achieved, using Chiraspher (Merck) as the chiral HPLC phase and the optical purity ascertained directly by HRGC with heptakis(3-O-acetyl-2,6-di-O-pentyl)-β-cyclodextrin (Lipodex D) as the chiral stationary phase. The absolute configurations of 4,5-dihydroxyhexanoic acid γ-lactones are assigned by 1H-NMR spectral data of diastereomeric α-methoxy-α-trifluoromethylphenylacetic acid (MTPA) esters, according to Mosher's model. Sensory qualities of the isomers are given.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010408
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    The determination of (-)-(S)- and (+)-(R)- ifosfamide in plasma using enantioselective gas chromatography: A validated assay for pharmacokinetic and clinical studies (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 235-238 
    Details
    ISSN: 0899-0042
    Keywords: ifosfamide enantiomers, GC chiral stationary phase, pharmacokinetic studies, clinical validation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An enantioselective gas chromatographic method has been developed and validated for the determination of the plasma concentration of the enantiomers of the anticancer drug ifosfamide (IFF). In this approach, the IFF enantiomers are separated from the plasma matrix by solid phase extraction, chromatographically resolved by gas chromatography on a chiral stationary phase, and detected by mass selective detection using selective ion monitoring. The assay has been validated for routine clinical and pharmacokinetic use and has a limit of detection in plasma of 250 ng/ml of each isomer.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010309
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    Optical enrichment of dansyl-rac-amino acids by formation of crystalline inclusion complexes with cyclodextrins (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 137-141 
    Details
    ISSN: 0899-0042
    Keywords: resolution by crystallization ; racemic mixture ; dansyl-D-leucine ; dansyl-L-leucine ; dansyl-D-norleucine ; dansyl-L-norleucine ; dansyl-D-phenylalanine ; dansyl-L-phenylalanine ; β-cyclodextrin ; γ-cyclodextrin ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Optical enrichment from racemic dansyl-leucine, dansyl-norleucine, and dansyl-phenylalanine with both β- and γ-cyclodextrins in water is reported. Initial crystallization yielded the dansyl-L-leucine isomer complexed in excess with β-cyclodextrin with an optical purity of 62-78% depending on experimental conditions. The optical purities obtained for L-norleucine and L-phenylalanine were 71 and 64%, respectively. The optical purity can be increased with continued recrystallization. The dansyl-D-leucine isomer was obtained in the mother liquor with an optical purity of 54-93% depending on experimental conditions. The optical purities obtained for D-norleucine and D-phenylalanine were 72 and 58%. The optical purity of the isomer depended on the molar ratio of host:guest and the pH value of the solution. Optimum enrichment of both enantiomers was achieved with host:guest ratios of 2 : 1 and 3 : 1. Although maximum crystalline yield of the dansyl-leucine/CD inclusion complex was obtained at a pH of 3.5, optical purity of both enantiomers was less than that obtained at other pHs. The influence of the molar ratio of host:guest and the pH value of the solution are discussed. This method is suitable for large-scale enantiomeric separations.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010207
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    Direct separation of albendazole sulfoxide enantiomers by liquid chromatography on a chiral column deriving from (S)-N-(3,5-dinitrobenzoyl)tyrosine: application to enantiomeric assays on plasma samples (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 142-153 
    Details
    ISSN: 0899-0042
    Keywords: enantiomeric separations ; chiral stationary phase ; Pirkle-type phases ; HPLC ; anthelmintics ; benzimidazole sulfoxides ; albendazole ; fenbendazole ; oxfendazole ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The direct enantiomeric resolution of albendazole sulfoxide (SOABZ), an anthelmintic drug belonging to the benzimidazole class, is reported on a chiral stationary phase (CSP) synthesized by covalent binding of (S)-N-(3,5-dinitrobenzoyl)tyrosine-O-(2-propen-1-yl) methyl ester on a γ-mercaptopropylsilanized silica gel. A comparison with the resolution achieved on commercially available Pirkle-type CSPs obtained from N-(3,5-dinitrobenzoyl) derivatives of (R)-phenyglycine or (S)-phenylalanine is described. Some structurally related chiral sulfoxides including oxfendazole (SOFBZ) are also studied. Optimization of the mobile phase nature and composition is investigated showing that a hexane-dioxane-ethanol ternary mixture affords an almost baseline resolution (Rs = 1.25); however, in this case, albendazole sulfone (SO2ABZ) is eluted between the two sulfoxide enantiomers; accordingly, a hexane-ethanol mobile phase would be preferred for biological samples containing both metabolites. The influence of temperature on the resolution is depicted with a hexane-ethanol mobile phase. Finally, application to the enantiomeric assays of SOABZ in plasmatic extracts of rat, sheep, bovin, and man after oral administration of albendazole (sulfoxidized to SOABZ and SO2ABZ) is reported. Some distortions in the enantiomeric ratios are evidenced depending on the species.
    Additional Material: 10 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010208
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    Joining hands (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 1-1 
    Details
    ISSN: 0899-0042
    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/chir.530010102
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    Determination of terbutaline enantiomers in biological samples using liquid chromatography with coupled columns (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 20-26 
    Details
    ISSN: 0899-0042
    Keywords: terutaline ; enantiomers ; determination ; liquid ; chromatography ; coupled columns ; cyclodextrin ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The purpose of this work was to develop and validate a method for the separation and determination of the enantiomers of terbutaline in plasma and intestinal juice. Terbutaline was extracted from plasma and intestinal juice by liquid-solid extraction on small C18 cartridges. The extract was then analyzed by coupled column liquid chromatography with amperometric detecton. For ciral separation a β-cyclodextrin phase was used.The within-day variation (Cv) on spiked plasma samples was in the rane 0.8-6.4% at 3.8-33.8 nmol/liter for the (-)-enantiomer, and 2.6-23.0% at 1.3-11.3 nmol/liter for the (+)-enantiomer. The between-day variation on spiked plasma samples was 5.5% at 10.7 nmol/liter and 13.6% at 4.3 nmol/liter for the (-)- and (+)-enantiomers, respectively. The within-day variation for inestinal juice was i the range 0.7-1.5% at 5.6-30.0 μmol/liter for the (+)-enantiomer.
    Additional Material: 7 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010107
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    A general criterion for molecular recognition: Implications for chiral interactions (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 69-79 
    Details
    ISSN: 0899-0042
    Keywords: chiral recognition ; three-point model ; distance matrix ; molecular graph ; molecular complexes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A general criterion is formulated for molecular recognition. The criterion for recognition is the ineqality of the distance matrices of complexes of different compounds with a resolving agent under ambient experimental conditions. It is shown how this criterion provides for an objective, cell-defined, and simple explanation for recognition of chiral compounds. This approach may be used to explain models (e.g., three-point of attachment1) and relationships for chiral recognition. It is also shown how one-, two-, or three-point mechanisms are equivalent in this formalism and could result in chiral recognition. Examples are used to illustrate how the so called one- or two-point mechanisms may be operative in many experimental findings. Symmetry rreqirements of resolving agents may also be derived from considerations of distance matrices. Finally, the reciprocal relationship of chiral resolving agents is easily derived from the present method of analysis.
    Additional Material: 11 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010113
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    Masthead (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989) 
    Details
    ISSN: 0899-0042
    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/chir.530010201
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    Letter to the editor (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 97-97 
    Details
    ISSN: 0899-0042
    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/chir.530010202
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    Preparation of chiral statonary phase from an α-amino phosphonate (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 57-62 
    Details
    ISSN: 0899-0042
    Keywords: chiral stationary phase ; α-amino phosphonate ; chromatographic separation of enantiomers ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A chiral statonary phase (CSP) derived from an N-(3,5-dinitrobenzoyl)-α-aminobenzylphosphonate has been prepared and evaluated for its utility in the direct separation of enantiomers. This CSP, 2, is structurally related to earlier N-(3,5-dinitrobenzoyl)-α-acids acid-derived phases (e.g., CSP 1), but the mode of attachment to the support is different. In scope; CSP 2 is qualitaively similar to CSP 1. However, it differs quantitatively from CSP 1, showing either greater or lesser selectivity for different pairs of enantiomers.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010111
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    Evaluation of π-acid chiral stationary phases deriving from tyrosine and related amino acids for the chromatographic resolution of racemates: Specific requirements for enantiorecognition ability (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 45-56 
    Details
    ISSN: 0899-0042
    Keywords: enantiomeric separations ; chiral stationary phases ; tyrosine chiral selector ; γ-mercaptopropyl silica gel ; HPLC ; SubFC ; preparative LC ; chiral recognition mechanisms ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chromatographic applications of three novel chiral stationary phases (CSPs) deriving from (S)-(N)-(3,5-dinitrobenzoyl)tyrosine are reported, under liquid chromatographic (LC) and subscritical fluid chromatographic (SubFC) conditions. Two grafting modes of the chiral moiety have been experimented starting either from γ-mercaptopropyl-silanized (type 1) or γ-aminopropyl-silanized (type 2) silica gels. For type 2 CSPs an evaluation of the stability of the amide linkage was achieved by means of SubFC; the relative contriution of ionic and covalent bindings to the ciral recognitio aility was then outlined. The chromatographic properties of these CSPs were compared with those of the corresponding CSPs deriving from phenylglycine, p-hydroxyphenylglycine, and phenylalanine for the resolution of some tertiary phosphine oxide, naphthoyl amide, and α-methylene γ-lactam enantiomers. Some simple requirements regarding the solute and CSP structures for chiral recognition ability can be inferred from these results. In addition, the resolutio of π-acid α-N-(3,5-dinitrobenzoyl)amino esters was investigated on these π-acid CSPs. An example of preparative scale chromatography is also presented.
    Additional Material: 9 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010110
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    Enantioselective inclusion complexation of 2,3,4,6-tetra-O-acetyl-D-glycopyranose as a chiral host with (+)-(r)-phenylethylamine: x-ray characterization of the complex (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 80-85 
    Details
    ISSN: 0899-0042
    Keywords: crystal structure ; inclusion ; chiral host ; complexation ; glucopyranose ; cellulose triacetate ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: X-ray analysis of the crystalline product obtained by reaction of 2,3,4,6-Tetra-O-acetyl-D-glycopyranose with phenylethylamine revealed the formation of a real one-to-one inclusion complex. This complexaion is highly stereoselective, because only the (+)-R-enantiomeric form of the amine is included. Analogies to the mode of complexation of cellulose triaceate with chiral molecules in „inclusion chromatography“ are discussed.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010114
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    Stereocontrolled synthesis of peptide bond isosteres (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 89-91 
    Details
    ISSN: 0899-0042
    Keywords: asmmetric induction ; bacterial cell wall ; D-Ala-D-Ala ; dipeptide ; peptidoglycan ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Absolute stereochemical control is employed in the synthesis of isosteres for dipeptide subunits 1; see Fig. (1) in which the amide linkage has been replaced by a trans carbon-caron double bond. The synthesis affords access to the four stereoisomers of 1 in which R and R' = CH3, including the isostere of D-alanine-d-alanine (D-ala-D-Ala), 2.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010116
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    Investigation on the enantiomeric impurity of epinephrine hydrochloride injections (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 92-93 
    Details
    ISSN: 0899-0042
    Keywords: ciral resolution ; high-performance liquid chromatography ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Epinephrine enantiomers were derived into diastereoisomers with the chiral reagent 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylisothiocyanate. The resolutions was carried out on a C18 column. The RS between (-)-R- and (+)-S-isomers was 2.3. The retention time could be changed by adding a proper amount of acetonirile into the mobile phase. The results showed that (+)-S-isomer in the epinephrine hydrochloride injections increased during the period of storage.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010117
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    The development of concepts of chiral discrimination (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 183-191 
    Details
    ISSN: 0899-0042
    Keywords: enantiomorphism ; dissymmetry ; chirality ; enantioselectivity ; diastereoselectivity ; steric complementarity ; asymmetric induction ; three-point contact ; circularly polarized radiation ; circular dichroism ; parity nonconservation ; electroweak interaction ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pasteur's conjecture (1860) that biomolecular homochirality arose from a chiral natural force as yet inaccessible in the laboratory was supplanted by Fischer's (1894) “key and lock” hypothesis of stereoselection in enantiomer to diastereomer conversions, whether in the laboratory or in living organisms. Elaborations of the “key and lock” hypothesis by Haldane (1930) and Pauling (1948) have been illustrated and supported with modification by X-ray diffraction crystal structures of enzyme-substrate complexes over the past quarter century.Two types of mechanism for the product diastereoselectivity in the reactions of an enantiomer with an achiral reagent, early proposed, have recent support: one proposes a quasidiastereomeric structure for the enantiomer attacked in the ground state, the other for the corresponding transition state of the reaction. Approaches to the differential biological activity of two enantiomers postulate either the complete binding of each isomer to a chiral receptor site, resulting in diastereomeric complexes with inequivalent bioactivities, or the differential binding of the two isomers to a set of three sites, with which only one isomer is sterically congruent.Biochemical homochirality, based on the chiral stereoselectivity of both biosynthetic and metabolic reactions, derives from the evolutionary pressure for a progressive enhancement of the kinetic efficiency and economy of those reactions. Recently Pasteur has been vindicated in part, and the problem of the original prebiotic enantiomeric excess left outstanding by Fischer has been solved. The unification of the electromagnetic with the weak interaction provided a universal chiral natural force, the electroweak interaction, which favours the chiral series selected during the course of biochemical evolution, both the D-sugars and the L-amino acids.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010302
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    Masthead (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989) 
    Details
    ISSN: 0899-0042
    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/chir.530010401
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    St. Mary's discussion forum: “Racemates and enantiomers: Scientific and regulatory aspects” (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 249-250 
    Details
    ISSN: 0899-0042
    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/chir.530010402
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    Chiral stationary phase high-performance liquid chromatographic resolution and absolute configuration of enantiomeric benzo[a]pyrene diol-epoxides and tetrols (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 276-283 
    Details
    ISSN: 0899-0042
    Keywords: benzo[a]pyrene diol-epoxides ; benzo[a]pyrene tetrols ; high-performance liquid chromatography ; chiral stationary phase ; optical isomers ; resolution of enantiomers ; absolute configuration ; circular dichroism spectra ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enantiomers of diastereomeric benzo[a]pyrene (BP) diol-epoxides, r-7,t-8-dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydro-BP (BP 7,8-diol-anti-9,10-epoxide), r----7,t-8-dihydroxy-c-9,10-epoxy-7,8,9,10-tetrahydro-BP (BP 7,8-diol-syn-9,10-epoxide), r-9,t-10-dihydroxy-t-7,8-epoxy-7,8,9,10-tetrahydro-BP (BP 9,10-diol-antiy7,8-epoxide), and several 7,8,9,10-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrenes (BP tetrols) were resolved by high-performance liquid chromatography (HPLC) using columns packed with either (R)-N-(3,5-dinitrobenzoyl)phenylglycine[(R)-DNBPG] or (S)-N-(3,5-dinitrobenzoyl)leucine [(S)-DNBL], which is either ionically or covalently bonded to γ-aminopropylsilanized silica. Resolution of enantiomers was confirmed by ultraviolet-visible absorption and circular dichroism spectral analyses. Resolved enantiomers of BP diol-epoxides were each hydrolyzed in acidic solution to a pair of diastereomeric tetrols which were separated by reversed-phase HPLC. Absolute stereochemistries of enantiomeric diol-epoxides were deduced by the absolute configuration of their hydrolysis products.
    Additional Material: 6 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010406
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    Crystal structure and absolute configuration of (+)546-[copy4Cl2]HDBT: An example of torsional isomerism (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 284-292 
    Details
    ISSN: 0899-0042
    Keywords: absolute configuration ; crystal structure ; resolution ; solid-state circular dichroism ; torsional isomerism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The crystal structure and absolute configuration of the (-)589-dibenzoylmonohydrogentartrate salt of the cation [Co(pyridine)4Cl2]+ have been determined from a three-dimensional X-ray analysis. Single crystals were grown from dimethylsulfoxide: space group P212121, Z = 4, and cell dimensions a = 21.463(4), b = 23.112(3), and c = 7.490(1) Å. Full-matrix least-squares refinement on F converged at R = 0.075, 196 variables and 2029 observations. The cation has pseudotetragonal coordinate geometry, with axial Cl and equatorial N atoms. The dihedral angles between the pyridine ligands and the equatorial plane are 47(1), 39(1), 50(1), and 45(1)° and torsional isomerism is responsible for the solid-state chiroptical properties of the cation. The preferential crystallization of the P atropisomer of the cation is attributed to a general electrostatic attraction between cation and anion.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010407
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    (-)-(S)-Flunoxaprofen and (-)-(S)-naproxen isocyanate: Two new fluorescent chiral derivatizing agents for an enantiospecific determination of primary and secondary amines (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 223-234 
    Details
    ISSN: 0899-0042
    Keywords: enantiomers ; diastereoisomeric ureas ; high-performance liquid chromatography (HPLC) ; fluorophores ; inversion of optical rotation ; antiarrhythmics ; propranolol ; plasma ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis and analytical testing of two new fluorescent chiral derivatizing agents (-)-(S)-flunoxaprofen and (-)-(S)-naproxen isocyanate, is described. In a few simple steps the free carboxylic acids [(S)-flunoxaprofen and (S)-naproxen] are activated with ethyl chloroformate/sodium azide and transformed to the corresponding isocyanates. The crystalline reaction products display high enantiomeric and chemical purity and stability. The direction of the optical rotation of both substances is inverse to that of the corresponding carboxylic acids. At ambient temperature the reagents swiftly react with primary and secondary amines, yielding highly fluorescent ureas. The applicability of the two reagents for the resolution of racemic amines was tested with a number of pharmaceuticals (antiarrhythmics, β-adrenergic antagonists, calcium channel blockers, centrally acting antidepressants). The diastereoisomeric derivatives were efficiently resolved and separated from side-products by means of normal and reversed-phase high-performance liquid chromatography (HPLC). The use and sufficient sensitivity of the two reagents for pharmacokinetic studies were demonstrated with a determination of plasma levels of propranolol enantiomers after oral administration of the racemic drug [80 mg (R,S)-propranolol-HCl] to two volunteers.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010308
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    Direct chromatographic separation of 2-arylpropionic acid enantiomers using tris(3,5-dimethylphenylcarbamate)s of cellulose and amylose as chiral stationary phases (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 239-242 
    Details
    ISSN: 0899-0042
    Keywords: optical resolution ; HPLC ; chromatography ; antiinflammatory drug ; ibuprofen ; ketoprofen ; flurbiprofen ; tiaprofenic acid ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Direct optical resolution of antiinflammatory drugs such as ibuprofen, ketoprofen, flurbiprofen, and tiaprofenic acid were attempted by high-performance liquid chromatography using tris(3,5-dimethylphenylcarbamate)s of cellulose and amylose as chiral stationary phases. Although ibuprofen was not sufficiently resolved, the other three 2-arylpropionic acids were completely resolved by amylose tris(3,5-dimethylphenylcarbamate). Ibuprofen was resolved as anilide derivative.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010310
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    The interaction of the enantiomers of carvedilol with α1- and β1-adrenoceptors (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 265-270 
    Details
    ISSN: 0899-0042
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The stereoselectivity of carvedilol, a novel β-adrenoceptor antagonist and vasodilator with one asymmetric carbon atom, was examined at α1- and β1-adrenoceptors in vitro and in vivo. (-)-(S)-Carvedilol is a potent, competitive antagonist of the β1-adrenoceptor-mediated positive chronotropic response to isoproterenol in guinea pig atrium, with a dissociation constant (KB) of 0.4 nM. (+)-(R)-Carvedilol was more than 100-fold less potent than the (-)-S-enantiomer as an antagonist of β;1-andrenoceptors, having a KB of approximately 45 nM. Consistent with these findings (-)-(S)-carvedilol (0.1 mg/kg, i.v.) produced a 25-fold rightward shift in the β1-adrenoceptor-mediated positive chronotropic response to isoproterenol in pithed rats, whereas the (+)-R-enantiomer had no β1-adrenoceptor blocking activity in vivo at this dose. In contrast to the marked degree of stereoselectivity observed at βl1-adrenoceptors, both (-)-(S)- and (+)-(R)-carvedilol produced equal antagonism of the α1----adrenoceptor-mediated vasoconstrictor response to norepinephrine in rabbit aorta, with KB values of 14 and 16 nM, respectively. Furthermore, in the pithed rat, the α1-adrenoceptor-mediated pressor dose-response curve to cirazoline was shifted approximately 6-fold to the right by both the (+)-R- and (-)-S-enantiomers of carvedilol at a dose of 1 mg/kg, i.v. In anesthetized spontaneously hypertensive rats, (-)-(S)-carvedilol was 6-fold more potent as an antihypertensive than (+)-(R)-carvedilol. The vasodilator and acute antihypertensive activity of carvedilol results from α1-andrenoceptor blockade produced by both enantiomers, and the concomitant β1-adrenoceptor blockade produced by the (-)-S-enantiomer, which prevents reflex tachycardia that can offset the antihypertensive response, leading to greater overall antihypertensive potency of (-)-(S)-carvedilol relative to the (+)-R-enantiomer. These data also suggest that distinct regions of the carvedilol molecule are responsible for blocking α1- and β1-adrenoceptors, with β1-adrenoceptor blockade resulting from an area of the molecule containing the asymmetric carbon atom, specifically the carbazolyloxy propanolamine moiety, and α1-adrenoceptor blockade resulting from a part of the molecule that does not contain the asymmetric carbon atom, most likely the phenoxyethylamine moiety.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010404
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  • 80
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    First announcement and call for papers (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 309-312 
    Details
    ISSN: 0899-0042
    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/chir.530010410
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  • 81
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    Mechanisms of chiral recognition in xenobiotic metabolism and drug-receptor interactions (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 7-9 
    Details
    ISSN: 0899-0042
    Keywords: substrate enantioselectivity ; product enantioselectivity ; Michaelis-Menten analysis ; intrinsic activity ; potency ; receptor affinity ; efficacy ; 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/chir.530010104
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  • 82
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    Pharmacologic implications of α-adrenocreceptor interactive parameters for epinephrine enantiomers in the rat vas deferens (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 14-19 
    Details
    ISSN: 0899-0042
    Keywords: affinity ; efficacy ; dissociation ; constants ; steroselectivity ; entropy ; enthalpy ; receptor ; interaction ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: After alkylation of a fraction of the total α-adrenoreceptors by phenoxybenzamine in rat vas deferens, the dissociation constants of (-)- and (+)-epinephrine in functional studies were 7 × 10-7 M and 2 × 10-5 M, respectively. In the adrenoreceptor-containing tissue fraction, when 3H-labeled WB4101 was used as the interacting ligand, for each enantiomer who affinity sites were found. Only the low-affinity dissociation consant for each isomer correlates with the constant obtained from the functional studies. If the change in Gibb's free energy. ΔG°, is calculated from the low-affinity binding constants, the values -8.1 and -6.2 kcal/mol for (-)- and (+)-isomer, respectively, are obained. The small difference in the value between isomers forms a hydrogen bond with the receptor. The interaction of epinephrine with this receptor appears to be driven largely by the entropy of the drug-receptor interaction with only a small nonsteroselective contribution from the enthalpy of ineraction.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010106
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  • 83
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    The stereochemical resolution of enantiomeric free and derivatized amino acids using and hplc chiral stationary phase based on immobilized α-chymotrypsin: Ciral separation due to solue structure or enzyme activity (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 38-44 
    Details
    ISSN: 0899-0042
    Keywords: column liquid chromatography ; chiral separations ; chymotrypsin on silica ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The stereochemical separation of free and derivatized amino acids on active α-chymotrypsin bonded to silica is governed by two mechanisms based on the structure of the solutes or on the enzymatic activity of the enzyme. Te deactivation of the hydrolytically active site of the enzyme demonstrated that a significant portion of the retention on this support is due to hydrophobic interactions at other sites. These sites appear to be stereoselective for the ester derivatives of amino acids but not for the other studied solutes.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010109
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  • 84
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    Moleclar imprinting by noncovalent interactions: Tailor-made chiral stationary phases of high selectivity and sample load capacity (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 63-68 
    Details
    ISSN: 0899-0042
    Keywords: optical resolution ; chromatography ; amino acid derivatives ; molecular recognition ; preparative ciral separation ; macroporous polymers ; mass transfer limitaions ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A moleclar imprinting technique based on electrostatic and hydrogen bonding interactions was used to prepare polymers of high selectvity for the original print molecule (D or L form of an amino acid derivative). In the chromatographic mode ig enantioselectivity was observed, in particular for amino acid amides and basic amino acid esters. As indicated y he broad peaks obtained, the mass transfer, including the kinetics of the binding and dissociation process, was slow and appeared to be slower in systems where a higher number of interactions between the solute and the stationary phase could be expected. In such systems enhanced selectivity was observed. For polymers prepared at a lower temperature the mass transfer was more rapid and a higher selectivity was observed, wich allowed the separations to be performed at room temperature. A more rapid mass transfer and a higher selectivity could also be achieved by increasing the column temperature. Furthermore the polymers showed a high sample load capacity and a high stability, and the can easily be prepared.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010112
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  • 85
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    The absolute configuration of benproperinium dihydrogen phosphate, an antitussive drug (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 86-88 
    Details
    ISSN: 0899-0042
    Keywords: stereochemistry ; stereoselective snthesis ; (S)-2-hydroxypropanoic acid ; chiral synthon ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The (+)- and (-)-enantiomers of benproperinium dihydrogen phosphate, an antitussive drug, have been assigned the R- and S-configurations, respectively, by syntheses of both enantiomers using (S)-2-hydroxypropanoic acid (L-lactic acid) as chiral synthon. The key intermediate, (S)-2-metyl-2-[-2-(phenylmethyl)phenoxy]ethyl p-toluenesulfonate, was subjected to an SN2-type reaction with piperidine furnishing (+)-(R)-benproperinium dihydrogen phosphate. (-)-(S)-Benproperinium dihydrogen phosphate was obtained by submitting the same tosylate to two consecutive SN2-type reactions with Br- and piperidine, respectively, acting as nucleophiles.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010115
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  • 86
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    Announcements (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 94-95 
    Details
    ISSN: 0899-0042
    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/chir.530010118
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  • 87
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    Stereoselectivity at muscarinic receptor subtypes: observations with the enantiomers of phenglutarimide (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 170-173 
    Details
    ISSN: 0899-0042
    Keywords: phenglutarimide enantiomers ; enantioselectivity ; antiparkinsonian drugs ; M1-selective antagonists ; rabbit vas deferens ; pirenzepine ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The affinity of the enantiomers of phenglutarimide at three muscarinic receptor subtypes was examined in vitro using field-stimulated rabbit vas deferens (M1 receptors) and guinea pig atria (M2α receptors) and ileum (M2β receptors). Extremely high stereoselectivity was observed and higher affinities (up to 6000-fold) were found for the (+)-S-enantiomer. The stereoselectivity ratios were different at the three subtypes, and the stereochemical demands made by the muscarinic receptors were most stringent at M1 receptors. (+)-(S)-Phenglutarimide was found to be a potent M1-selective antagonist (pA2 at M1 = 8.53). Its receptor selectivity profile is qualitatively similar to that of pirenzepine. (-)-(R)-Phenglutarimide showed no comparable discriminatory properties.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010212
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  • 88
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    Masthead (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989) 
    Details
    ISSN: 0899-0042
    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/chir.530010101
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  • 89
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    The FDA perspective on the development of stereoisomers (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 2-6 
    Details
    ISSN: 0899-0042
    Keywords: optical isomers ; stereochemistry ; enantiomers ; Food and Drug Administration ; drug development ; drug regulation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The current regulatory position of the Food and Drug Administration is discussed with regard to the approval of racemates and pure stereoisomers. Circumstances in which stereochemically sensitive analytical methods are necessay to ensure the safety and efficacy of a drug are described. Regulatory guidelines are interpreted for applications for the approval of a pure enantiomer in which the racemate is marketed, for the approval of eitehr a racemate or a pure enantiomer in which neither is marketed, and for clinical investigations to compare the safety and efficacy of a racemate and its enantiomers. Examples of te basis for such regulation are drawn from historical situations (thalidomide, benoxaprofen) as well as currently marketed drugs (arylproionic acids, disopyramide, indacrinone).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010103
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  • 90
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    Liquid chromatographic separation of anomeric forms of saccharides with cyclodextrin bonded phases (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 27-37 
    Details
    ISSN: 0899-0042
    Keywords: mutarotation ; sugars ; carbohydrates ; isomeric ; separation ; temperature effects ; selectvity ; optimization ; hemiacetal ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A brief review of sugar stereochemistry is given. The separation of 84 different pairs of anomers was accomplished on both α- and β-cyclodextrin columns. Five different mobile phases were evaluated. The separation of anomers temperature, flow rate, and so on. The separation of anomers that mutarotate is somewhat more difficult than those that do not. Prior knowledge as to the rate of mutaroation is useful so that the chromatographic conditions can be arranged to minimize any deleterious effects on the separation.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010108
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  • 91
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    Stereoselective sulfation of terbutaline by the rat liver cytosol: evaluation of experimental approaches (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 121-126 
    Details
    ISSN: 0899-0042
    Keywords: stereoselective metabolism ; sulfate conjugation ; in vitro sulfation ; sympathomimetic amines ; chiral separation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Little is known about the stereochemistry of sulfation of chiral phenolic drugs. In this study we examined several in vitro approaches to this question, using (+)-, (-)-, or (±)-terbutaline as the substrate and the rat liver cytosol as the phenolsulfotransferase enzyme source. The cosubstrate PAPS was either generated by the cytosol from inorganic sulfate and ATP or added to the cytosol. The intact sulfate conjugates formed were determined by HPLC. Using the PAPS generating system, which is best suited for the production of relatively large quantities of sulfate conjugates, with the individual enantiomers as substrates, (+)-terbutaline was conjugated to a much greater extent than (-)-terbutaline; the (+)/(-)-enantiomer ratio was 7.3 ± 0.3 (mean ± SE). When (±)-terbutaline was the substrate and chiral derivatization was employed to separate the sulfate enantiomers formed, a similar (+)/(-)-enantiomer ratio of 7.9 ± 0.2 was obtained. With PAP35S added to the cytosol, an approach best suited for kinetic studies, the substrate concentration dependence of sulfation could be determined. The Km app for this reaction was identical for (+)- and (-)-terbutaline. However, the Vmax app was 8.1 ± 0.4 times greater for (+)-terbutaline. This study for the first time shows enantioselectivity in sulfation of a chiral phenolic drug. The experimental approaches used should be valuable for human studies of stereoselectiven sulfation of terbutaline and other chiral drugs.
    Additional Material: 4 Ill.
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    URL: http://dx.doi.org/10.1002/chir.530010205
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  • 92
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    Resolution of some β-hydroxyphenethylamines as N-(3,5-dinitrobenzoyl) amides on chiral stationary phases derived from cinchona alkaloids (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 161-166 
    Details
    ISSN: 0899-0042
    Keywords: chromatography ; chirality ; chiral recognition ; β-aminoalcohols ; stereochemistry ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Three chiral stationary phases, obtained by derivatizing γ-mercaptopropylsilanized silica gel with quinine, quinidine, and cinchonidine, have been employed in the resolution of N-acyl derivatives of β-hydroxyphenethylamines. The use of circular dichroism for detection and NMR analysis of analyte-selector mixtures provides an experimental basis for preliminary assignment of a recognition mechanism.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010210
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  • 93
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    Optical resolution of some biologically active compounds by chiral liquid chromatography on BSA-silica (resolvosil) columns (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 154-160 
    Details
    ISSN: 0899-0042
    Keywords: enantiomers ; chiral discrimination ; drugs ; hydrophobic interaction ; biopolymers ; elution order ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Optical resolution on the analytical scale of a number of racemic pharmaceuticals and some other biologically active compounds has been studied using immobilized bovine serum albumin (BSA) as the stationary phase. For some of the compounds the elution order was determined by the use of optically enriched fractions obtained from a preceding passage of a sample through a preparative column containing microcrystalline triacetylcellulose (MCTA). The reversal in the sign of optical rotation shown in the polarimetric elution profile from the latter, combined with the integrated peak area ratio obtained on resolution on the analytical column, gave directly the order of elution. For one of the benzothiadiazines studied (bendroflumethiazide), increasing the pH of the mobile phase produced opposite effects on the retention of the two enantiomers, leading to a large effect on the separation factor. For many of the compounds studied, high separation factors (α 〉 2) could be achieved.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010209
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  • 94
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    Announcements (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 178-179 
    Details
    ISSN: 0899-0042
    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/chir.530010215
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  • 95
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    Pharmacokinetics of the enantiomers of terbutaline after repeated oral dosing with racemic terbutaline (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 174-177 
    Details
    ISSN: 0899-0042
    Keywords: pharmacokinetics ; terbutaline ; enantiomers ; human ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Terbutaline is a β2-agonist and administered as the racemic mixture. The pharmacokinetics of the separate enantiomers differ with respect to degree of absorption and clearance. In the present study, repeated doses of racemic terbutaline were given to six healthy volunteers. Plasma was analyzed for the concentrations of the two enantiomers. The observed plasma concentrations at steady state differed from those predicted from the values observed after single dose administration of the separate enantiomers. The difference between the observed and predicted values can be tentatively explained by a combined influence of (-)-terbutaline on the absorption of (+)-terbutaline and the influence of (+)-terbutaline on the elimination of (-)-terbutaline. The results have implications for the interpretation of effect/concentration studies with terbutaline, but do not affect the doses used in clinical practice.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010213
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  • 96
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    Response to letter to the editor (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 98-98 
    Details
    ISSN: 0899-0042
    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/chir.530010203
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  • 97
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    Cytochrome P-450-catalyzed asymmetric epoxidation of simple prochiral and chiral aliphatic alkenes: species dependence and effect of enzyme induction on enantioselective oxirane formation (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 127-136 
    Details
    ISSN: 0899-0042
    Keywords: enantioselective epoxidation ; cytochrome P-450-dependent monooxygenases ; species dependence of microsomal epoxidation ; product enantioselectivity ; substrate enantioselectivity ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantioselectivity of the in vitro conversion of simple prochiral and chiral aliphatic alkenes into oxiranes by liver microsomes of untreated or induced (phenobarbital) rats, of untreated or induced (phenobarbital, benzo[α] pyrene) mice, and of humans was determined by complexation gas chromatography. The enantiomeric excess (ee) of the epoxides extends from 0 (trimethyloxirane) to 50% (ethyloxirane). The configuration (R or S) of the enantiomers formed in excess is consistent for homologous oxiranes but is species dependent and in some cases influenced by enzyme induction. Enantioselectivity differences of aliphatic alkene epoxidation by human liver microsomes of four individuals are negligible.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010206
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  • 98
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    A vivid model of chiral recognition (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 167-169 
    Details
    ISSN: 0899-0042
    Keywords: enantioselectivity ; three-point model ; chiral receptors ; chiral separations ; didactic model ; elusion of the three-point model ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Hands can be used to demonstrate the three-point model of chiral recognition. The points of attachment are thumb, forefinger, and middle finger. This vivid model has the advantages of simplicity, perspicuity, and availability at any time, although two persons are necessary. It can be shown that two interactions are not sufficient for chiral recognition but that three attractive or two attractive and one repulsive attraction are needed. It can also be used to explain some possibilities of weakening or elusion of the three-point model.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010211
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  • 99
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    Electronic Resource
    Methiodide of the GABA antagonist (+)-bicuculline is levorotatory (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 178-179 
    Details
    ISSN: 0899-0042
    Keywords: CD spectra ; optical rotation ; phthalideisoquinoline base and salts ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The appearance of positive charge on the nitrogen moiety of phthalideisoquinoline alkaloids brings about a strong change in the intensities of CD Cotton effects. Hence the optical rotations of enantiomeric salts and their parent base of identical configuration are often of opposite sign. Thus, the name (+)-bicuculline-methiodide for the methiodide salt of (+)-bicuculline is false.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010214
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    Electronic Resource
    Electronic Resource
    Stereochemical influences upon the opioid ligand activities of 4-alkyl-4-arylpiperidine derivatives (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 202-208 
    Details
    ISSN: 0899-0042
    Keywords: opioid ligand ; 4-arylpiperidines ; conformation, NMR ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis and stereochemistry (configuration and preferred solute conformation) of some 4-alkyl (methyl, n-propyl, isobutyl)-4-(3-hydrxyphenyl)-1-methylpiperidines and corresponding 3-methyl diastereoisomeric pairs are reported, together with their in vivo and in vitro activities as opioid ligands. All potent agonists exhibit a preference for axial 4-aryl chair conformations when protonated, and stereochemical analogies with rigid opioids of the benzomorphan class are discussed. Antagonist properties are found in compounds with preference for equatorial 4-aryl chairs, notably the cis 3,4-dimethyl derivative.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010305
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