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  • 1
    Electronic Resource
    Electronic Resource
    Steric and conformational effects in the dehalogenation of 2-halo sugar derivatives with tributylstannane (1993)
    s.l. : American Chemical Society
    The @journal of organic chemistry 58 (1993), S. 1821-1826 
    Details
    ISSN: 1520-6904
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/jo00059a037
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  • 2
    Electronic Resource
    Electronic Resource
    Halogenation of 1,5-anhydrohex-1-enitols (glycals). Influence of the C-6 substituent (1986)
    s.l. : American Chemical Society
    The @journal of organic chemistry 51 (1986), S. 3479-3485 
    Details
    ISSN: 1520-6904
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/jo00368a015
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  • 3
    Electronic Resource
    Electronic Resource
    Organ distribution and tumor uptake of annamycin, a new anthracycline derivative with high affinity for lipid membranes, entrapped in multilamellar vesicles (1993)
    Springer
    Cancer chemotherapy and pharmacology 32 (1993), S. 190-196 
    Details
    ISSN: 1432-0843
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Annamycin (Ann) is a lipophilic, non-cross resistant anthracycline antibiotic that is easily amenable to formulation in a wide variety of liposomal carriers. We studied the organ distribution and tumor uptake of Ann entrapped in multilamellar vesicles (L-Ann), free annamycin (F-Ann), and doxorubicin (DOX) in C57BL/6 mice bearing advanced subcutaneous B16 melanoma tumors. L-Ann was composed of DMPC: DMPG: Ann at a molar ratio of 7:3:0.7. Mean particle size was 1.88±0.89 μm, and the entrapment efficiency was 93.08%±2.96%. F-Ann was prepared as a suspension (particle size ≤0.2 μm) in 10% DMSO. Drug levels were measured by fluorescence spectrometry after extraction with chloroform. The extraction ratio ranged between 60% and 90% for both drugs in most tissues. Compared with those of DOX, organ AUCs of L-Ann were threefold higher in plasma and brain, twofold higher in liver and kidney, six-fold higher in lung, ninefold higher in spleen, and tenfold higher in B16 tumors. Compared with F-Ann, organ AUCs of L-Ann were twofold higher in plasma, liver, and B16 tumors and were twofold lower in brain. Heart AUCs were similar with all three drugs. Higher tumor uptake was associated with a faster penetration and more prolonged retention of Ann in tumor tissue compared with those of DOX. The results obtained indicate significant differences in organ distribution between L-Ann and DOX as a result of the higher affinity of Ann for lipid membranes and the use of the liposomes as a delivery system. The potential clinical relevance of the increased uptake of L-Ann in B16 tumors, lung, and brain is being investigated.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00685834
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  • 4
    Electronic Resource
    Electronic Resource
    Cellular pharmacology of the partially non-cross-resistant anthracycline annamycin entrapped in liposomes in KB and KB-V1 cells (1994)
    Springer
    Cancer chemotherapy and pharmacology 34 (1994), S. 109-118 
    Details
    ISSN: 1432-0843
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract. The in vitro cytotoxicity, cellular pharmacology, and DNA lesions induced by the lipophilic anthracycline annamycin (Ann) were studied in KB and KB-V1 (multidrug-resistant) cells. Ann was tested in suspension in saline and 10% dimethylsulfoxide (DMSO: final concentration, 0.05% – 0.5%) or entrapped in multilamellar liposomes (median size, 1.57 μm). Doxorubicin (Dox) was about twice as cytotoxic as Ann or liposome-entrapped Ann (L-Ann) against KB cells. Both Ann and L-Ann displayed a partial lack of cross-resistance with Dox (resistance indices: 〉60 for Dox, 4.7 for Ann, 4.0 for L-Ann). Accumulation of Ann in KB and KB-V1 cells was consistently about 2 – 3 and 10 – 20 times higher, respectively, than that of Dox. Cellular retention of Ann in KB and KB-V1 cells was about 2 and 30 times higher, respectively, than that of Dox as a result of the different efflux patterns of the two drugs: Dox was not effluxed from KB cells but was significantly effluxed from KB-V1 cells (66% at 1 h, whereas Ann efflux was similar in both cell lines (about 50% at 1 h). Dox retention in KB-V1 cells was increased by a factor of 2 in the presence of verapamil or cyclosporine A, but Ann retention was not. In addition, accumulation of Dox in KB-V1 cells was enhanced by the metabolic inhibitor deoxyglucose/azide and the membrane carboxylic ionophore monensin, whereas accumulation of Ann was not affected by either agent. All these findings indicate significant differences in the cellular transmembrane transport systems between Dox and Ann and suggest that Ann efflux is not mediated by P-glycoprotein. Liposome entrapment reduced by a factor of 1.3 – 2.0 the cellular accumulation of Ann without affecting its cytotoxicity. As compared with Dox, both Ann and L-Ann induced 3 times more DNA double- and single-strand breaks in KB cells. In KB-V1 cells, Dox did not induce DNA damage, whereas the extent of DNA breaks induced by both Ann and L-Ann was similar to that induced by Dox in KB cells. Our results indicate (1) that the lack of cross-resistance between Ann and Dox is associated with a markedly enhanced accumulation and retention of Ann in KB-V1 cells and (2) that the type of liposomes used does not significantly affect the cellular effects of Ann.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00685927
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  • 5
    Electronic Resource
    Electronic Resource
    Phase I study of liposomal annamycin (2000)
    Springer
    Cancer chemotherapy and pharmacology 46 (2000), S. 427-432 
    Details
    ISSN: 1432-0843
    Keywords: Key words Anthracycline ; Phase I study ; Pharmacokinetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Annamycin is a highly lipophilic anthracycline with the ability to bypass the MDR-1 mechanism of cellular drug resistance. In this phase I study, annamycin entrapped in liposomes was administered by a 1- to 2-h intravenous infusion at 3-week intervals. Thirty-six patients with relapsed solid tumors were treated and 109 courses were administered at doses ranging from 3 to 240 mg/m2. The dose-limiting toxicity was thrombocytopenia. Five patients had a probable allergic reaction, requiring discontinuation of treatment in one. Treatment was well tolerated otherwise. No cardiac toxicity was seen on endomyocardial biopsy of four patients studied. There was limited gastrointestinal toxicity and no alopecia. No objective tumor responses were observed. Pharmacokinetic studies at 24, 120 and 240 mg/m2 showed a biexponential plasma concentration-versus-time profile. There was a linear relationship between the dose and the maximal plasma concentration with relatively constant plasma clearance values. The maximum tolerated dose (MTD) for liposomal annamycin defined in this study is 210 mg/m2. Because of a subsequent change in the formulation of the drug, future studies will use 190 mg/m2 as the MTD.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s002800000177
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  • 6
    Electronic Resource
    Electronic Resource
    Liposomal formulation and antitumor activity of 14-O-palmitoyl-hydroxyrubicin (1992)
    Springer
    Cancer chemotherapy and pharmacology 30 (1992), S. 267-271 
    Details
    ISSN: 1432-0843
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The 14-O-palmitoyl ester of 3′-deamino-3′-hydroxydoxorubicin was synthesized to study the liposomal formulation and biological activity properties conferred by the attachment of a lipophilic group to position 14 of the anthracycline molecule. The entrapment efficiency of 14-O-palmitoyl-hydroxyrubicin in multilamellar vesicles composed of dimyristoylphosphatidyl choline and dimyristoylphosphatidyl glycerol was 〉99%. In addition, the stability of liposomes containing 14-O-palmitoyl-hydroxyrubicin was 〉99% at 14 days as assessed by the amount of drug leaking out of the liposomes and the absence of crystals of free drug in the liposome pellet. Esterilication at position 14 did not significantly decrease the potency of the parent compound 3′-hydroxydoxorubicin. Liposome-entrapped 14-O-palmitoyl-hydroxyrubicin was significantly more active than doxorubicin against two murine tumor models. Against ip L-1210 leukemia, liposome-entrapped 14-O-palmitoyl-hydroxyrubicin injected i.p. into mice at doses of 60 and 80 mg/kg resulted in a %T/C value (median survival of treated/control animals ×100) of 〉600, with 3–4 of 6 animals being cured, where-as in the same experiments, doxorubicin injected at the optimal dose (10 mg/kg) resulted in a %T/C value of 340, with 1 of 6 animals being cured. In animals bearing liver metastases of M-5076 reticulosarcoma, liposome-entrapped 14-O-palmitoyl-hydroxyrubicin showed significant antitumor activity when given on a three-i.v.-injection scheule of 20 mg/kg on days 4, 8, and 12 (%T/C, 175), whereas doxorubicin injected at optimal doses of 6–8 mg/kg on the same days was devoid of antitumor activity (%T/C, 129–133). These results indicate that esterification at position 14 enhances the affinity of this type of compounds for lipid bilayers without negatively affecting their biological activity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00686293
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  • 7
    Electronic Resource
    Electronic Resource
    Lyophilized preliposomal formulation of the non-cross-resistant anthracycline annamycin: effect of surfactant on liposome formation, stability and size (1996)
    Springer
    Cancer chemotherapy and pharmacology 39 (1996), S. 103-108 
    Details
    ISSN: 1432-0843
    Keywords: Key words Liposome ; Annamycin ; Lyophilization ; Reconstitution
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract  We report a method of preparing a submicron and stable liposome formulation of the non-cross-resistant anthracycline annamycin. The lipids were dimyristoylphosphatidyl choline (DMPC) and dimyristoylphosphatidyl glycerol (DMPG) at a 7 : 3 molar ratio and the optimal lipid : drug ratio was 50 : 1 (w/w). The selected formulation was a preliposome lyophilized powder that contained the phospholipids, annamycin, and Tween 20. The liposome suspension was obtained on the day of use by adding normal saline at 37 °C (1 ml/mg annamycin) and hand shaking for 1 min. The presence of Tween 20 was essential in shortening the reconstitution step (from 〉2 h to 1 min), avoiding the early formation of free drug crystals, and reducing the median particle size by tenfold (from 1.5 μm to 0.15 μm) without destroying the liposome vesicles. At room temperature, the preliposome powder was chemically stable for 〉3 months, and the liposome suspension was chemically and physically stable for 〉24 h. The in vitro cytotoxicity of the formulation was equivalent to that of the same lipid composition prepared by the standard evaporation method. The results of the study indicate that small amounts of surfactant may be used to enhance the reconstitution step and reduce the size of liposome suspensions obtained from lyophilized preliposome powders. The formulation described is being used for ongoing clinical trials with liposomal annamycin.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s002800050544
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  • 8
    Electronic Resource
    Electronic Resource
    Cellular pharmacology of the partially non-cross-resistant anthracycline annamycin entrapped in liposomes in KB and KB-V1 cells (1994)
    Springer
    Cancer chemotherapy and pharmacology 34 (1994), S. 109-118 
    Details
    ISSN: 1432-0843
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The in vitro cytotoxicity, cellular pharmacology, and DNA lesions induced by the lipophilic anthracycline annamycin (Ann) were studied in KB and KB-V1 (multidrug-resistant) cells. Ann was tested in suspension in saline and 10% dimethylsulfoxide (DMSO: final concentration, 0.05%–0.5%) or entrapped in multilamellar liposomes (median size, 1.57 μm). Doxorubicin (Dox) was about twice as cytotoxic as Ann or liposome-entrapped Ann (L-Ann) against KB cells. Both Ann and L-Ann displayed a partial lack of cross-resistance with Dox (resistance indices: 〉60 for Dox, 4.7 for Ann, 4.0 for L-Ann). Accumulation of Ann in KB and KB-V1 cells was consistently about 2–3 and 10–20 times higher, respectively, than that of Dox. Cellular retention of Ann in KB and KB-V1 cells was about 2 and 30 times higher, respectively, than that of Dox as a result of the different efflux patterns of the two drugs: Dox was not effluxed from KB cells but was significantly effluxed from KB-V1 cells (66% at 1 h. whereas Ann efflux was similar in both cell lines (about 50% at 1 h). Dox retention in KB-V1 cells was increased by a factor of 2 in the presence of verapamil or cyclosporine A, but Ann retention was not. In addition, accumulation of Dox in KB-V1 cells was enhanced by the metabolic inhibitor deoxyglucose/azide and the membrane carboxylic ionophore monensin, whereas accumulation of Ann was not affected by either agent. All these findings indicate significant differences in the cellular transmembrane transport systems between Dox and Ann and suggest that Ann efflux is not mediated by P-glycoprotein. Liposome entrapment reduced by a factor of 1.3–2.0 the cellular accumulation of Ann without affecting its cytotoxicity. As compared with Dox, both Ann and L-Ann induced 3 times more DNA double-and single-strand breaks in KB cells. In KB-V1 cells, Dox did not induce DNA damage, whereas the extent of DNA breaks induced by both Ann and L-Ann was similar to that induced by Dox in KB cells. Our results indicate (1) that the lack of cross-resistance between Ann and Dox is associated with a markedly enhanced accumulation and retention of Ann in KB-V1 cells and (2) that the type of liposomes used does not significantly affect the cellular effects of Ann.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00685927
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  • 9
    Electronic Resource
    Electronic Resource
    Synthesis of new 1-C-(2-furyl)-and 3-C-(2-furyl)-hexopyranosides and 3-C-(2-furyl)-daunorubicin analogs (1991)
    Springer
    Monatshefte für Chemie 122 (1991), S. 419-423 
    Details
    ISSN: 1434-4475
    Keywords: Daunorubicin analogs ; Electrophilic substitution ; Furan ; Glycals ; Unsaturated carbohydrates ; C-Glycosides
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Die Reaktion von Furan mit 3,4-Di-O-acetyl-L-rhamnal (1) ergab eine Mischung von epimeren 3-C-(2-Furyl)-glycalen3 und4 und 1-C-(2-Furyl)-hex-2-enopyranosen5 und6. Die Glycale3 und4 wurden zu den 2-Deoxy-glycosiden9–13 und 3′-Deamino-3′-C-(2-furyl)-daunorubicinen15 und16 transformiert. Hex-2-enopyranosyl5 wurde mit Osmiumtetroxid/N-methylmorpholin-N-oxid zum C-Glycosidcis-hydroxyliert.
    Notes: Summary Reaction of furan with 3,4-di-O-acetyl-L-rhamnal (1) afforded a mixture of epimeric 3-C-(2-furyl) glycals3 and4 and 1-C-(2-furyl)-hex-2-enopyranoses5 and6. Glycals3 and4 were transformed to 2-deoxy-glycosides9–13 and 3′-deamino-3′-C-(2-furyl)daunorubicines15 and16. Hex-2-enopyranosyl5 wascis hydroxylated with osmium tetroxide/N-methylmorpholine N-oxide to C-glycoside14.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809663
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  • 10
    Electronic Resource
    Electronic Resource
    Interaction of doxorubicin and its derivatives with DNA: Elucidation by resonance Raman and surface-enhanced resonance Raman spectroscopy (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Biospectroscopy 3 (1997), S. 307-316 
    Details
    ISSN: 1075-4261
    Keywords: doxorubicin ; intercalation ; resonance Raman ; SERRS ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Physics
    Notes: The interactions of doxorubicin and its derivatives, hydroxyrubicin and adriamycinone, with DNA were studied by resonance Raman (RR) and surface-enhanced resonance Raman scattering (SERRS) spectroscopy. The π-π interaction between the chromophore of the drug and DNA base pairs has been shown to downshift the skeletal stretching mode ∼ 1440 cm-1 by 8, 5, and 4 cm-1 for doxorubicin, hydroxyrubicin, and adriamycinone, respectively. The additional effects of intercalation with DNA on the RR and SERRS spectra for hydroxyrubicin are similar to those for doxorubicin. However, different effects are observed for adriamycinone. These results indicate that the sugar moiety is necessary to maintain the maximum van der Waals contact between the chromophore and the DNA base pairs and that the amine group in the amino sugar is more favored than the hydroxyl group. © 1997 John Wiley & Sons, Inc. Biospectroscopy 3: 307-316, 1997
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
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