Synthesis and antifungal activity of oxygenated cholesterol derivatives.
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 microg/mL.
Brunel
Jean Michel
JM
Laboratoire Synthèse et Etude de Substances Naturelles à Activités Biologiques (SESNAB), IMRN INRA 1111, Faculté des Sciences et Techniques de St Jérôme, Université Paul Cézanne, Aix-Marseille III, 13397 Marseille Cedex 20, France. bruneljm@yahoo.fr
Loncle
Céline
C
Vidal
Nicolas
N
Dherbomez
Michel
M
Letourneux
Yves
Y
D000666:Amphotericin B / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D002784:Cholesterol / Q000138:chemical synthesis* / Q000494:pharmacology*; D004351:Drug Resistance; D006801:Humans; D007659:Ketones; D008825:Miconazole / Q000494:pharmacology; D010100:Oxygen / Q000737:chemistry; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D007659:Ketones; D008825:Miconazole; D000666:Amphotericin B; D002784:Cholesterol; D010100:Oxygen