scholarly journals Comparative studies on cell stimulatory, permeabilizing and toxic effects induced in sensitive and multidrug resistant fungal strains by amphotericin B (AMB) and N-methyl-N-D-fructosyl amphotericin B methyl ester (MFAME).

2000 ◽  
Vol 47 (1) ◽  
pp. 133-140 ◽  
Author(s):  
J Szlinder-Richert ◽  
B Cybulska ◽  
J Grzybowska ◽  
E Borowski ◽  
R Prasad
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Methyl Ester ◽  
Amphotericin B ◽  
Mammalian Cells ◽  
Parent Compound ◽  
Multidrug Resistant ◽  
Solubility In Water ◽  
Good Solubility ◽  
Low Toxicity ◽  
Amphotericin B Methyl Ester

N-Methyl-N-D-fructosyl-amphotericin B methyl ester (MFAME) is a new derivative of amphotericin B, which is characterised by low toxicity to mammalian cells and good solubility in water of its salts. The antifungal activity and effects of MFAME towards Candida albicans and Saccharomyces cerevisiae multidrug resistant MDR(+) and sensitive MDR(-) strains was compared with those of parent compound. The results obtained indicate that MDR(+) S. cerevisiae was sensitive to MFAME as well as to AMB. MFAME exhibited the same effects on fungal cells studied as parent antibiotic. The two antibiotics, depending on the dose applied induced cell stimulation, K+ efflux, and/or had a toxic effect.

scholarly journals Comparative in vitro studies on liposomal formulations of amphotericin B and its derivative, N-methyl-N-D-fructosyl amphotericin B methyl ester (MFAME).

2002 ◽  
Vol 49 (1) ◽  
pp. 67-75 ◽  
Author(s):  
Barbara Cybulska ◽  
Karolina Kupczyk ◽  
Joanna Szlinder-Richert ◽  
Edward Borowski
Keyword(s):  
Methyl Ester ◽  
Amphotericin B ◽  
Mammalian Cells ◽  
Biological Properties ◽  
Antagonistic Effect ◽  
Molar Ratio ◽  
Selective Toxicity ◽  
Liposomal Formulations ◽  
Amphotericin B Methyl Ester

N-Methyl-N-D-fructosyl amphotericin B methyl ester (MFAME) is a semisynthetic derivative of the antifungal antibiotic amphotericin B (AMB). In contrast to the parent antibiotic, the derivative is characterised by low toxicity to mammalian cells and good solubility in water of its salts. Comparative studies on biological properties of free MFAME, AMB and their liposomal formulations were performed. To obtain liposomal forms, the antibiotics were incorporated into small unilamellar vesicles composed of dimyristoyl phosphatidylcholine (DMPC) and DMPC:cholesterol or ergosterol, 8:2 molar ratio. The effectivity of the liposomal and free forms of AMB and MFAME were compared by determination of fungistatic and fungicidal activity against Candida albicans ATCC 10261, potassium release from erythrocytes, and haemolysis. The results obtained indicate that in contrast to AMB, incorporation of MFAME into liposomes did not further improve its selective toxicity. Studies on the antagonistic effect of ergosterol and cholesterol on the antifungal activity of the antibiotics indicated that sterol interference was definitely less pronounced in the case of MFAME than in the case of AMB.

scholarly journals N-Methyl-N-D-fructosyl amphotericin B methyl ester (MF-AME), a novel antifungal agent of low toxicity: monomer/micelle control over selective toxicity.

2000 ◽  
Vol 47 (1) ◽  
pp. 121-131 ◽  
Author(s):  
B Cybulska ◽  
I Gadomska ◽  
J Mazerski ◽  
J G E Borowski ◽  
M Cheron ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Amphotericin B ◽  
Mammalian Cells ◽  
Spectroscopic Properties ◽  
Water Soluble ◽  
Selective Toxicity ◽  
Human Red Blood Cells ◽  
Amphotericin B Methyl Ester

Rational chemical modification of amphotericin B (AMB) led to the synthesis of sterically hindered AMB derivatives. The selected optimal compound, N-methyl-N-D-fructosyl amphotericin B methyl ester (MF-AME) retains the broad spectrum of antifungal activity of the parent antibiotic, and exhibits a two orders of magnitude lower toxicity in vivo and in vitro against mammalian cells. Comparative studies of MF-AME and AMB comprising the determination of the spectroscopic properties of monomeric and self-associated forms of the antibiotics, the investigation of the influence of self-association on toxicity to human red blood cells, and of the antibiotic-sterol interaction were performed. On the basis of the results obtained it can be assumed that the improvement of the selective toxicity of MF-AME could in part be a consequence of the diminished concentration of water soluble oligomers in aqueous medium, and the better ability to differentiate between cholesterol and ergosterol.

Subchronic Toxicity Studies of N-D-Ornithyl Amphotericin B Methyl Ester in Dogs and Rats

1985 ◽  
Vol 5 (4) ◽  
pp. 737-753
Author(s):  
TOBIAS MASSA ◽  
DINESH P. SINHA ◽  
JERRY D. FRANTZ ◽  
MARY E. FILIPEK ◽  
RAYMOND C. WEGLEIN ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Amphotericin B ◽  
Subchronic Toxicity ◽  
Toxicity Studies ◽  
Amphotericin B Methyl Ester

The Perpendicular Orientation of Amphotericin B Methyl Ester in Hydrated Lipid Bilayers Supports the Barrel-Stave Model

Biochemistry ◽  
2019 ◽  
Vol 58 (17) ◽  
pp. 2282-2291 ◽  
Author(s):  
Tomoya Yamamoto ◽  
Yuichi Umegawa ◽  
Masaki Yamagami ◽  
Taiga Suzuki ◽  
Hiroshi Tsuchikawa ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Amphotericin B ◽  
Lipid Bilayers ◽  
Perpendicular Orientation ◽  
Amphotericin B Methyl Ester

Stereoselective syntheses of the 14-hydroxy epimers of amphotericin B methyl ester

1993 ◽  
pp. 1829 ◽  
Author(s):  
Benjamin J. Costello ◽  
Michael J. Driver ◽  
William S. MacLachlan ◽  
Andrew W. Taylor
Keyword(s):  
Methyl Ester ◽  
Amphotericin B ◽  
Amphotericin B Methyl Ester ◽  
Stereoselective Syntheses

scholarly journals N-Methyl-N-D-fructopyranosylamphotericin B Methyl Ester, New Amphotericin B Derivative of Low Toxicity.

1997 ◽  
Vol 50 (8) ◽  
pp. 709-711 ◽  
Author(s):  
JOLANTA GRZYBOWSKA ◽  
PAWEL SOWINSKI ◽  
JERZY GUMIENIAK ◽  
TERESA ZIENIAWA ◽  
EDWARD BOROWSKI
Keyword(s):  
Methyl Ester ◽  
Amphotericin B ◽  
Low Toxicity
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