Conjugation of amino-containing drugs to polysaccharides by tosylation: Amphotericin B-arabinogalactan conjugates

Biomaterials

Volumn 25, Issue 15, 2004, Pages 3049-3057

  Ehrenfreund Kleinman, Tirsta ^a   Golenser, Jacob ^b   Domb, Abraham J ^a,b  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Amphotericin B; Arabinogalactan; Mesylate; Tosylate; Water soluble conjugate

Indexed keywords

AMINO ACIDS; BIOMATERIALS; MICROORGANISMS; ORGANIC POLYMERS; PATHOLOGY; POLYSACCHARIDES; WATER; YEAST;

CONJUGATION; UNBOUND DRUGS;

DRUG PRODUCTS;

AMINE; AMINO ACID DERIVATIVE; AMPHOTERICIN B; ANTIFUNGAL AGENT; ANTILEISHMANIAL AGENT; ARABINOGALACTAN; CHLORIDE; MESYLIC ACID DERIVATIVE; ORGANIC COMPOUND; POLYSACCHARIDE; TOLUENESULFONIC ACID DERIVATIVE; WATER;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIFUNGAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CANDIDA ALBICANS; CHEMICAL BOND; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CONJUGATION; DRUG SOLUBILITY; DRUG STABILITY; HEMOLYSIS; LEISHMANIA MAJOR; MALE; MOUSE; NONHUMAN; PARASITE; PATHOGENESIS; PRIORITY JOURNAL; SHEEP ERYTHROCYTE; TOSYLATION; TOXICITY; YEAST;

CANDIDA; CANDIDA ALBICANS; LEISHMANIA MAJOR; OVIS ARIES;

EID: 1142297579     PISSN: 01429612     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2003.09.080     Document Type: Article

References (36)

1. Meares C.F. Prospective in bioconjugate chemistry. 1993;American Chemical Society, Washington, DC.
2. Maeda H. Domb A.J. Polymeric site-specific pharmacotherapy. 1994;95-116 Wiley, Chichester, UK.
3. Mehvar R. Dextrans for targeted and sustained delivery of therapeutics and imaging agents. J Control Release. 69:2000;1-25.
4. Larsen C, editor. Dextran prodrugs. Physico-chemical and chemical aspects in relation to in vivo properties. Copenhagen: Villadsen & Christensen; 1990.
5. Vlieghe P., Clerc T., Pannecouque C., Witvrouw M., De-Clercq E., Salles J.P., Karous J.L. Synthesis of new covalently bound κ-carrageenan-AZT conjugates with improved anti HIV activities. J Med Chem. 45:2002;1275-1283.
6. Sedlak M., Buchta V., Kubicova L., Simunek P., Holcapek M., Kasparova P. Synthesis and characterization of a new amphotericin B-methoxy (ethylene glycol) conjugates. Bioorg Med Chem Lett. 11:2001;2833-2835.
7. Kratz F., Beyer U., Schutte M.T. Drug-polymer conjugates containing acid-cleavable bonds. Crit Rev Ther Drug Carrier System. 16:1999;245-288.
8. Heindel N.D., Zhao H.R., Leiby J., Vandongen J.M., Lacey C.J., Lima D.A., Shabsoung B., Buzby J.H. Hydrazide pharmaceuticals as conjugates to polyaldehyde dextran. syntheses, characterization, and stability Bioconjugate Chem. 1:1990;77-82.
9. Hwang D.G., Scott M.E., Hedaya E. Synthesis and characterization of digoxin-phospholipid conjugates. Bioconjugate Chem. 1:1990;309-313.
10. Duncan R. Drug-polymer conjugates. potential for improved chemotherapy Anti Cancer Drugs. 3:1992;175-210.
11. Adams M.F., Douglas C. Arabinogalactan - a review of the literature. TAPPI. 46:1963;544-558.
12. Nazareth M.R., Narayanan V.L., Bhatia V.A. Studies on the larch arabinogalactan II. J Pharm Sci. 50:1961;564-567.
13. Groman E.V., Enriquez P.M., Chu J., Josephson L. Arabinogalactan for hepatic drug delivery. Bioconjugate Chem. 5:1994;547-556.
14. Kaneo Y., Ueno T., Tanaka T., Iwase H., Yamaguchi Y., Uemura T. Pharmacokinetics and biodisposition of fluorescein labeled arabinogalactan in rats. Int J Pharm. 201:2000;59-69.
15. Gallis H.A., Drew R.H., Pickard W.W. Amphotericin B. 30 years of clinical experience Rev Infect Dis. 12:1990;308-329.
16. Ellis D. Amphotericin B. spectrum and resistance J Antimicrob Chemother. 49:2002;7-10.
17. Sundar S. Treatment of visceral leishmaniasis. Med Microbiol Immunol. 190:2001;89-92.
18. Thakur C.P., Narain S., Kumar N., Hassan S.M., Jha D.K., Kumar A. Amphotericin-B is superior to sodium antimony gluconate in the treatment of Indian post kala azar dermal leishmaniasis. Ann Trop Med Parasitol. 91:1997;611-616.
19. Butler W.T. Pharmacology, toxicity, and therapeutic usefulness of amphotericin-B. JAMA. 195:1996;127-131.
20. Sabra R., Branch R.A. Amphotericin B nephrotoxicity. Drug Saf. 5:1990;94-108.
21. Chabot G.G., Pazdur R., Valeriote F.A., Baker L.H. Pharmacokinetics and toxicity of continuous infusion of amphotericin-B in cancer patients. J Pharm Sci. 78:1989;307-310.
22. Brajtburg J., Bolard J. Carrier effects on biological activity of amphotericin-B. Clin Microbiol Rev. 9:1996;512-531.
23. Clayette P., Martin M., Beringue V., dereuddre-Bosquet N., Adjou K.T., Seman M., Dormont D. Effects of MS-8209, an amphotericin B derivative, in tumor necrosis factor alpha synthesis and human immunofeficiency virus replication in macrophages. Antimicrob Agents Chemother. 44:2000;405-407.
24. Cybulska B., Gadomska I., Mazerski J., Grzybowska J., Borowski E., Cheron M., Bolard J. N-methyl-N-D-fructosyl amphotericin B methyl ester, a novel antifungal agent of low toxicity. monomer/micelle control over selective toxicity Acta Biochim Pol. 47:2000;121-131.
25. Dupont B. Overview of the lipid formulations of amphotericin B. J Antimicrob Chemother. 49:2002;31-36.
26. Yardley V., Croft S. Activity of liposomal amphotericin-B against experimental cutaneous leishmaniasis. Antimicrob Agents Chemother. 41:1997;752-756.
27. Conover C.D., Zhao H., Longley C.B., Shum K.L., Greenwald R.B. Utility of poly(ethylene glycol) conjugation to create prodrugs of amphotericin B. Bioconjugate Chem. 14:2003;661-666.
28. Greenwald R.B., Choe Y.H., Mcguire J., Conover C.D. Effective drug delivery by PEGylated drug conjugates. Adv Drug Deliv Rev. 55:2003;217-250.
29. Seldak M., Buchta V., Kubicova L., Simunek P., Holcapek M., Kasparova P. Synthesis and characterization of a new amphotericin B-methoxypoly(ethylene glycol) conjugate. Bioorg Med Chem Lett. 11:2001;2833-2835.
30. Enriquez P.M., Jung C., Josephson L., Tennant B.C. Conjugation of adenine-arabinoside 5′-monophosphate to arabinogalactan-synthesis, characterization, and antiviral activity. Bioconjugate Chem. 6:1995;195-202.
31. Nogawa M., Ishihara T., Akaike T., Maruyama A. Polyethylenimine/ arabinogalactan conjugate as a hepatocyte specific gene carrier. STP Param Sci. 11:2001;97-102.
32. Ehrenfreund Kleinman T., Azzam T., Falk R., Polacheck I., Golenser J., Domb A.J. Synthesis and characterization of novel water soluble amphotericin B-arabinogalactan conjugates. Biomaterials. 23:2002;1327-1335.
33. Golenser J., Frankenburg S., Ehrenfreund T., Domb A.J. Efficacious treatment of experimental leishmaniasis with amphotericin B-arabinogalactan water-soluble derivatives. Antimicrob Agents Chemother. 43:1999;2209-2214.
34. Falk R., Domb A.J., Polacheck I. A novel injectable water-soluble amphotericin B-arabinogalactan conjugate. Antimicrob Agents Chemother. 43:1999;1975-1981.
35. National Committee for Clinical Laboratories Standards. Reference method for broth dilution antifungal susceptibility testing of yeasts. Approved standard M27-A. National Committee for Clinical Laboratories Standards, Wayne, PA, 1997.
36. Zarif L., Graybill J.R., Perlin D., Najvar L., Bocanegra R., Mannino R.J. Antifungal activity of amphotericin B cochleates against Candida albicans infection in a mouse model. Antimicrob Agents Chemother. 44:2000;1463-1469.