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Arch Pharm (Weinheim) ; 337(3): 152-5, 2004 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-15038060

RESUMO

The marine fatty acid (+/-)-2-methoxytetradecanoic acid was synthesized in two steps (71% overall yield) starting from commercially available methyl-2-hydroxy-tetradecanoate. The title compound was antifungal against Candida albicans (ATCC 14053) in RPMI medium and Aspergillus niger (ATCC 16404) and Cryptococcus neoformans (ATCC 66031) in SDB medium at the minimum inhibitory concentration (MIC) of 100 mM, which compares to the fungitoxicity of a 2-iodotetradecanoic acid against the same fungi. The title compound was also five to ten times more cytotoxic than capric acid to C. albicans and A. niger in the tested medium but comparable in cytotoxicity to either capric acid and its 2-methoxylated analog to C. neoformans. The antifungal activity of (+/-)-2-methoxytetradecanoic acid is explained in terms of inhibition of N-myristoyltransferase.


Assuntos
Antifúngicos/síntese química , Antifúngicos/farmacologia , Miristatos/síntese química , Miristatos/farmacologia , Ácidos Mirísticos/síntese química , Ácidos Mirísticos/farmacologia , Aciltransferases/antagonistas & inibidores , Aciltransferases/biossíntese , Aciltransferases/farmacocinética , Anfotericina B/farmacologia , Aspergillus niger/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Cryptococcus neoformans/efeitos dos fármacos , Ácidos Graxos/síntese química , Técnicas In Vitro
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