Inhibition of 2,3-oxidosqualene-lanosterol cyclase in Candida albicans by pyridinium ion-based inhibitors | Zendy

Robert C. Goldman | Zendy; Dorothy Zakula | Zendy; John O. Capobianco | Zendy; Bradley A. Sharpe | Zendy; John H. Griffin | Zendy

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Inhibition of 2,3-oxidosqualene-lanosterol cyclase in Candida albicans by pyridinium ion-based inhibitors

Author(s) -

Robert C. Goldman,

Dorothy Zakula,

John O. Capobianco,

Bradley A. Sharpe,

John H. Griffin

Publication year - 1996

Publication title -

antimicrobial agents and chemotherapy

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 2.07

H-Index - 259

eISSN - 1070-6283

pISSN - 0066-4804

DOI - 10.1128/aac.40.4.1044

Subject(s) - lanosterol , cyclase , ergosterol , candida albicans , chemistry , stereochemistry , squalene , biochemistry , pyridinium , sterol , biology , enzyme , microbiology and biotechnology , cholesterol , medicinal chemistry

The N-(4E,8E)-5,9,13-trimethyl-4,8,12-tetradecatrien-1- ylpyridinium and N-(4E,8E)-5,9,13-trimethyl-4,8,12-tetradecatrien-1- ylpicolinium cations were evaluated for their ability to inhibit 2,3-oxidosqualene-lanosterol cyclase activity in Candida albicans. Both compounds inhibited fungal growth, were fungicidal, and resulted in the accumulation of squalene epoxide concurrent with a decrease in ergosterol, monomethyl sterols, and lanosterol, as was expected for the specific inhibition of 2,3-oxidosqualene-lanosterol cyclase activity. These compounds are electron-poor aromatic mimics of a monocyclized transition state or high-energy intermediate formed from oxidosqualene, which may explain their selective action.

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