Synthesis and antifungal activity of oxygenated cholesterol derivatives

被引：51

作者：

Brunel, JM

Loncle, C

Vidal, N

Dherbomez, M

Letourneux, Y

机构：

[1] Univ Aix Marseille 3, Fac Sci & Tech St Jerome, IMRN,SESNAB, INRA 1111,Lab Synth & Etud Subst Nat Activ Biol, F-13397 Marseille, France

[2] IUT Rochelle, F-17026 La Rochelle, France

来源：

STEROIDS | 2005年 / 70卷 / 13期

关键词：

oxygenated sterols; antifungal activity; antimicrobial activity;

D O I：

10.1016/j.steroids.2005.06.007

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 [生物化学与分子生物学]; 081704 [应用化学];

摘要：

A series of oxygenated cholesterol derivatives were prepared from new synthetic methods and evaluated for their in vitro antimicrobial properties against human pathogens. The activity was highly dependent on the structure of the different compounds involved. The best results were obtained with hydroxy ketones 2, 4 and 5 and diketone 7 exhibiting activities against S. cerevisiae (ATCC 28383) and Candida albicans (CIP 1663-86). For example, compound 2 exhibited high activities against C. albicans (CIP 1663-86) and Amphotericine B and miconazole resistant strain C. albicans (CIP 1180-79) at a concentration of 1.5 mu g/mL. (c) 2005 Elsevier Inc. All rights reserved.

引用

页码：907 / 912

页数：6

共 28 条

[1]

BELL JJ, 1976, J BIOL CHEM, V251, P1745

[2]

BERGER CL, 1989, PHOTOPHERESIS REV, V3, P1

[3]

Synthesis of 25-aminosterols, new antifungal agents [J].

Beuchet, P ;

Dherbomez, M ;

Elkiel, L ;

Charles, G ;

Letourneux, Y .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (11) :1599-1600

[4]

Synthesis of 6(α,β)-aminocholestanols as ergosterol biosynthesis inhibitors [J].

Beuchet, P ;

El kihel, L ;

Dherbomez, M ;

Charles, G ;

Letourneux, Y .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (24) :3627-3630

[5]

Relation between the Molecular Electrostatic Potential and activity of some FF-MAS related sterol compounds [J].

Boer, DR ;

Kooijman, H ;

van der Louw, J ;

Groen, M ;

Kelder, J ;

Kroon, J .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (10) :2653-2659

[6]

CHOLESTEROL, 7-KETOCHOLESTEROL AND 25-HYDROXYCHOLESTEROL UPTAKE STUDIES AND EFFECT ON "3-HYDROXY-3-METHYLGLUTARYL-COENZYME A REDUCTASE-ACTIVITY IN HUMAN FIBROBLASTS [J].

BRESLOW, JL ;

LOTHROP, DA ;

SPAULDING, DR ;

KANDUTSCH, AA .

BIOCHIMICA ET BIOPHYSICA ACTA, 1975, 398 (01) :10-17

[7]

BRUNEL JM, 2000, EUR J ORG CHEM, P3897

[8]

BRUNEL JM, 2000, CURR CANCER DRUG TAR, V5, P267

[9]

CHEMICAL-STRUCTURE OF STEROLS THAT ACTIVATE OOCYTE MEIOSIS [J].

BYSKOV, AG ;

ANDERSEN, CY ;

NORDHOLM, L ;

THOGERSEN, H ;

XIA, GL ;

WASSMANN, O ;

ANDERSEN, JV ;

GUDDAL, E ;

ROED, T .

NATURE, 1995, 374 (6522) :559-562

[10]

Cas E. Dei, 1991, MYCOSES, V34, P167

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