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Fungicidal activity of truncated analogues of dihydrosphingosine.

Thevissen, Karin; Hillaert, Ulrik; Meert, Els M K; Chow, Kuen K; Cammue, Bruno P A; Van Calenbergh, Serge; François, Isabelle E J A.

Bioorg Med Chem Lett ; 18(13): 3728-30, 2008 Jul 01.

Article in English | MEDLINE | ID: mdl-18524581

ABSTRACT

The minimal fungicidal concentration (MFC) of dihydrosphingosine (DHS), phytosphingosine (PHS), and five short-chain DHS derivatives was determined for Candida albicans and Candida glabrata. In this respect, a C15- and a C17-homologue of DHS showed a 2- to 10-fold decreased MFC as compared to native DHS (i.e. C18-DHS). DHS derivatives that were active, that is, comprising 12, 15, 17, or 18 carbon atoms, induced accumulation of reactive oxygen species (ROS) in C. albicans.

Subject(s)

Antifungal Agents/chemical synthesis , Sphingosine/analogs & derivatives , Animals , Antifungal Agents/chemistry , Candida albicans/metabolism , Candida glabrata/metabolism , Carbon/chemistry , Chemistry, Pharmaceutical/methods , Drug Design , Humans , Models, Chemical , Molecular Conformation , Oxygen/chemistry , Reactive Oxygen Species , Sphingosine/chemical synthesis , Sphingosine/chemistry , Technology, Pharmaceutical/methods

ABSTRACT

Subject(s)

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