A photophysical study on the role of bile salt hydrophobicity in solubilizing amphotericin B aggregates

Journal of Pharmaceutical Sciences

Volumn 98, Issue 11, 2009, Pages 4153-4160

  Selvam, Susithra ^a   Andrews, Maneesha Esther ^a   Mishra, Ashok K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Absorption spectroscopy; Amphotericin B; Bile salts; Biocompatibility; Cholates; Deoxycholates; Dimeric amphotericin B; Drug interaction; Fluorescence spectroscopy; Solublization

Indexed keywords

AMPHOTERICIN B; ANTIFUNGAL AGENT; BILE SALT; BIOSURFACTANT; CHOLIC ACID; DEOXYCHOLATE SODIUM; TAUROCHOLIC ACID; TAURODEOXYCHOLIC ACID;

ANISOTROPY; ARTICLE; BIOCOMPATIBILITY; CONTROLLED STUDY; DRUG ABSORPTION; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG SOLUBILITY; FLAME PHOTOMETRY; HYDROPHOBICITY; LIFESPAN; STEADY STATE;

EID: 70349637456     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21718     Document Type: Article

References (27)

1. Torrado JJ, Espada R, Ballesteros MP, Tarrado- Santiago S. 2008. Amphotericin B formulations and drug targetting. J Pharm Sci 97:2405-2425.
2. Brajtburg J, Bolard J. 1996. Carrier effects on biological activity of amphotericin B. Clin Microbiol Rev 9:512-531. (Pubitemid 26366536)
3. Kleinberg M. 2006. What is the current and future status of conventional amphotericin B? Intl J Antimicrob Agents 27S:S12-S16.
4. Hann IM, Prentice HG. 2001. Lipid-based amphotericin B: A review of the last 10 years of use. Intl J Antimicorb Agents 17:161-169. (Pubitemid 32229893)
5. Fukui H, Koike T, Saheki A, Sonoke S, Tomii Y, Seki J. 2003. Evaluation of the efficacy and toxicity of amphotericin B incorporated in lipid nano-sphere (LNS®). Intl J Pharm 263:51-60. (Pubitemid 37087932)
6. Risovic V, Boyd M, Choo E, Wasan KM. 2003. Effect of lipid-based oral formulations on plasma and tissue amphotericin B concentrations and renal toxicity in male rats. Antimicrob Agents Chemother 47:3339-3342. (Pubitemid 37229601)
7. Yu BG, Okano T, Kataoka K, Kwon GS. 1998. Polymeric micelles for drug delivery: solubilization and haemolytic activity of amphotericin B. J Control Release 53:131-136. (Pubitemid 28218696)
8. Lamy-Freund MT, Ferreira FNV, Schreier S. 1989. Polydispersity of aggregates formed by the polyene antibiotic amphotericin B and deoxycholate. A spin label study. Biochim Biophys Acta 981:207-212.
9. Gaboriau F, Cheron M, Petit C, Bolard J. 1997. Heat-induced superaggregation of amphotericin B reduces its in vitro toxicity: A new way to improve its therapeutic index. Antimicrob Agents Chemother 41:2345-2351. (Pubitemid 27467538)
10. Petit C, Cheron M, Joly V, Rodrigues JM, Bolard J, Gaboriau F. 1998. In vivo therapeutic efficacy in experimental murine mycoses of a new formulation of deoxycholate-amphotericin B (Fungizone) obtained by mild heating. J Antimicrob Chemother 42:779-785.
11. O'Connor CI, Wallace RG. 1985. Physico-chemical behavior of bile salts. Adv Colloid Interface Sci 22:1-111.
12. Martin C, Thongborisute J, Takeuchi H, Yamamoto H, Kawashima Y, Alpar HO. 2005. Cholesterol-bile salt vesicles as potential delivery vehicles for drug and vaccine delivery. Intl J Pharm 298:339-343. (Pubitemid 40910739)
13. Chae SY, Son S, Lee M, Jang M, Nah J. 2005. Deoxycholic acid-conjugated chitosan oligosaccharide nanoparticles for efficient gene carrier. J Contr Release 109:330-344. (Pubitemid 41737274)
14. Small DM, Carey MC. 1969. Micellar properties of dihydroxy and trihydroxy bile salts: Effects of counterion and temperature. J Colloid Interface Sci 31:382-395.
15. Santhanalakshmi J, Shantha Lakshmi G, Aswal VK, Goyal PS. 2001. Small-angle neutron scattering study of sodium cholate and sodium deoxycholate interacting micelles in aqueous medium. Proc Indian Acad Sci (Chem Sci) 113:55-62. (Pubitemid 32370016)
16. Mukhopadhyay S, Maitra U. 2004. Chemistry and biology of bile acids. Curr Sci 87:1666-1683.
17. Herec M, Gagos M, Gruszecki WI. 2003. Dimers of polyene antibiotic amphotericin B detected by means of fluorescence spectroscopy: molecular organization in solution and in lipid membranes. J Photochem Photobiol B 69:49-57.
18. Stoodley R, Wasan KM, Bizzotto D. 2007. Fluorescence of amphotericin B-deoxycholate (Fungizone) monomers and aggregates and the effect of heat-treatment. Langmuir 23:8718-8725. (Pubitemid 47294277)
19. Gagos M, Koper R, Gruszecki WI. 2001. Spectrophotometric analysis of organisation of dipalmitoylphosphatidylcholine bilayers containing the polyene antibiotic amphotericin B. Biochim Biophys Acta 1511:90-98.
20. Tancrede P, Barwicz J, Jutras S, Gruda I. 1990. The effect of surfactants on the aggregation state of amphotericin B. Biochim Biophys Acta 1030:289-295.
21. Barwicz J, Christian S, Gruda I. 1992. Effect of the aggregation state of amphotericin B on its toxicity to mice. Antimicrob Agents Chemother 36:2310-2315.
22. Susithra S, Mishra AK. 2008. Disaggregation of amphotericin B by sodium deoxycholate micellar aggregates. J Photochem Photobiol B: Biol 93:66-70.
23. Lakowicz JR. 2006. Principles of fluorescence spectroscopy. 3rd edition, New York: Springer Publishers.
24. Sugioka H, Matsuoka K, Moroi Y. 2003. Temperature effect on formation of sodium cholate micelles. J Colloid Interface Sci 259:156-162. (Pubitemid 36324550)
25. Chapman D, Penkett SA, Small DM. 1969. Studies on simple and mixed bile salt micelles by nuclear magnetic resonance spectroscopy. Biochim Biophys Acta 176:178-189.
26. Moreno MA, Frutos P, Ballesteros MP. 2001. Lyophilized lecithin based oil-water microemulsions as a new and low toxic delivery system for amphotericin b. Pharm Res 18:344-351. (Pubitemid 32595823)
27. Espada R, Valdespina S, Alfonso C, Rivas G, Ballesteros MP, Torrado JJ. 2008. Effect of aggregation state on the toxicity of different amphotericin b preparations. Intl J Pharm 361:64-69.