Fungicidal activity of truncated analogues of dihydrosphingosine

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

doi:10.1016/j.bmcl.2008.05.067

Fungicidal activity of truncated analogues of dihydrosphingosine

Bioorg Med Chem Lett. 2008 Jul 1;18(13):3728-30. doi: 10.1016/j.bmcl.2008.05.067. Epub 2008 May 20.

Authors

Karin Thevissen¹, Ulrik Hillaert, Els M K Meert, Kuen K Chow, Bruno P A Cammue, Serge Van Calenbergh, Isabelle E J A François

Affiliation

¹ Centre of Microbial and Plant Genetics (CMPG), Katholieke Universiteit Leuven, Kasteelpark Arenberg 20, 3001 Heverlee, Belgium.

PMID: 18524581
DOI: 10.1016/j.bmcl.2008.05.067

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.

MeSH terms

Animals
Antifungal Agents / chemical synthesis*
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 / analogs & derivatives*
Sphingosine / chemical synthesis
Sphingosine / chemistry
Technology, Pharmaceutical / methods

Substances

Antifungal Agents
Reactive Oxygen Species
Carbon
phytosphingosine
Sphingosine
safingol
Oxygen