Literature DB >> 2357943

Influence of net charge on the aggregation and solubility behaviour of amphotericin B and its derivatives in aqueous media.

J Mazerski1, J Grzybowska, E Borowski.   

Abstract

The poor solubility of polyene antibiotics in aqueous media limits their application in the therapy of systemic fungal infections. In the present paper we have demonstrated that the ionic state (net electrical charge) of the antibiotic molecule is an important factor in determining the aggregation and solubility properties of amphotericin B and its derivatives. A multi-step model of polyene self-association in aqueous media has been proposed as an explanation for the fact that some major differences are observed when aggregation is monitored by different techniques.

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Year:  1990        PMID： 2357943     DOI： 10.1007/bf02427375

Source DB:  PubMed          Journal:  Eur Biophys J        ISSN： 0175-7571            Impact factor:   1.733


  10 in total

1.  Biologically active N-acyl derivatives of polyene macrolide antifungal antibiotics.

Authors:  C P SCHAFFNER; E BOROWSKI
Journal:  Antibiot Chemother (Northfield)       Date:  1961-11

2.  Structural studies on aqueous and hydroalcoholic solutions of a polyene antibiotic: amphotericin B.

Authors:  H Rinnert; C Thirion; G Dupont; J Lematre
Journal:  Biopolymers       Date:  1977-11       Impact factor: 2.505

3.  Quantitative structure-activity relationships in amphotericin B derivatives.

Authors:  M Chéron; B Cybulska; J Mazerski; J Grzybowska; A Czerwiński; E Borowski
Journal:  Biochem Pharmacol       Date:  1988-03-01       Impact factor: 5.858

4.  Polyene macrolide derivatives. I. N-acylation and esterification reactions with amphotericin B.

Authors:  W Mechlinski; C P Schaffner
Journal:  J Antibiot (Tokyo)       Date:  1972-04       Impact factor: 2.649

5.  The synthesis of amides of polyene macrolide antibiotics.

Authors:  L Falkowski; A Jarzebski; B Stefańska; E Bylec; E Borowski
Journal:  J Antibiot (Tokyo)       Date:  1980-01       Impact factor: 2.649

6.  N-glycosyl derivatives of polyene macrolide antibiotics.

Authors:  L Falkowski; J Golik; P Kołlodziejczyk; J Pawlak; J Zielinski
Journal:  J Antibiot (Tokyo)       Date:  1975-03       Impact factor: 2.649

7.  Methyl esters of trimethylammonium derivatives of polyene macrolide antibiotics.

Authors:  L Falkowski; B Stefańska; J Zieliński; E Bylec; J Golik; P Kołodziejczyk; E Borowski
Journal:  J Antibiot (Tokyo)       Date:  1979-10       Impact factor: 2.649

8.  Synthesis and structure-activity relationships of amides of amphotericin B.

Authors:  A Jarzebski; L Falkowski; E Borowski
Journal:  J Antibiot (Tokyo)       Date:  1982-02       Impact factor: 2.649

9.  Interaction between phospholipid bilayer membranes and the polyene antibiotic amphotericin B: lipid state and cholesterol content dependence.

Authors:  J Bolard; M Seigneuret; G Boudet
Journal:  Biochim Biophys Acta       Date:  1980-06-20

10.  N-aminoacyl derivatives of polyene macrolide antibiotics and their esters.

Authors:  J J Wright; J A Albarella; L R Krepski; D Loebenberg
Journal:  J Antibiot (Tokyo)       Date:  1982-07       Impact factor: 2.649
  10 in total
  16 in total

1.  Channels formed by amphotericin B covalent dimers exhibit rectification.

Authors:  Minako Hirano; Yuko Takeuchi; Nobuaki Matsumori; Michio Murata; Toru Ide
Journal:  J Membr Biol       Date:  2011-03-20       Impact factor: 1.843

2.  A new look at the antibiotic amphotericin B effect on Candida albicans plasma membrane permeability and cell viability functions.

Authors:  Barbara Chudzik; Mateusz Koselski; Aleksandra Czuryło; Kazimierz Trębacz; Mariusz Gagoś
Journal:  Eur Biophys J       Date:  2015-01-04       Impact factor: 1.733

Review 3.  Amphotericin B membrane action: role for two types of ion channels in eliciting cell survival and lethal effects.

Authors:  B Eleazar Cohen
Journal:  J Membr Biol       Date:  2010-11-18       Impact factor: 1.843

4.  Conformational properties of amphotericin B amide derivatives--impact on selective toxicity.

Authors:  H Resat; F A Sungur; M Baginski; E Borowski; V Aviyente
Journal:  J Comput Aided Mol Des       Date:  2000-10       Impact factor: 3.686

5.  Plasma protein binding of amphotericin B and pharmacokinetics of bound versus unbound amphotericin B after administration of intravenous liposomal amphotericin B (AmBisome) and amphotericin B deoxycholate.

Authors:  Ihor Bekersky; Robert M Fielding; Dawna E Dressler; Jean W Lee; Donald N Buell; Thomas J Walsh
Journal:  Antimicrob Agents Chemother       Date:  2002-03       Impact factor: 5.191

6.  Cooperative partition model of nystatin interaction with phospholipid vesicles.

Authors:  Ana Coutinho; Manuel Prieto
Journal:  Biophys J       Date:  2003-05       Impact factor: 4.033

7.  FTIR spectroscopic study of molecular organization of the antibiotic amphotericin B in aqueous solution and in DPPC lipid monolayers containing the sterols cholesterol and ergosterol.

Authors:  Mariusz Gagoś; Marta Arczewska
Journal:  Eur Biophys J       Date:  2012-07-26       Impact factor: 1.733

8.  Self-association of the polyene antibiotic nystatin in dipalmitoylphosphatidylcholine vesicles: a time-resolved fluorescence study.

Authors:  A Coutinho; M Prieto
Journal:  Biophys J       Date:  1995-12       Impact factor: 4.033

9.  Cation conductance and efflux induced by polyene antibiotics in the membrane of skeletal muscle fiber.

Authors:  N Shvinka; G Caffier
Journal:  Biophys J       Date:  1994-07       Impact factor: 4.033

10.  Nystatin-, mycoheptin- and levorin-induced conductance in the membrane of frog skeletal muscle fibres.

Authors:  N E Shvinka; G Caffier
Journal:  Eur Biophys J       Date:  1995       Impact factor: 1.733
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