Synthesis and apoptogenic activity of fluorinated ceramide and dihydroceramide analogues

S De Jonghe; I Van Overmeire; J Gunst; A De Bruyn; C Hendrix; S Van Calenbergh; R Busson; D De Keukeleire; J Philippé; P Herdewijn

doi:10.1016/s0960-894x(99)00553-3

Synthesis and apoptogenic activity of fluorinated ceramide and dihydroceramide analogues

Bioorg Med Chem Lett. 1999 Nov 1;9(21):3159-64. doi: 10.1016/s0960-894x(99)00553-3.

Authors

S De Jonghe¹, I Van Overmeire, J Gunst, A De Bruyn, C Hendrix, S Van Calenbergh, R Busson, D De Keukeleire, J Philippé, P Herdewijn

Affiliation

¹ University of Gent, Faculty of Pharmaceutical Sciences, Laboratory for Medicinal Chemistry, Belgium.

PMID: 10560744
DOI: 10.1016/s0960-894x(99)00553-3

Abstract

Short-chain 3-fluoro-(dihydro)ceramide analogues are synthesized from L-serine using diethylaminosulfur trifluoride (DAST) as fluorinating agent. The apoptogenic activity of these compounds was measured in three different cell lines and compared with their hydroxylated counterparts.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Apoptosis / drug effects*
Ceramides / chemical synthesis*
Ceramides / pharmacology
Diethylamines / chemistry
Fluorine / chemistry
Fluorine Compounds / chemical synthesis*
Fluorine Compounds / pharmacology
Humans
Lymphocytes / drug effects
Tumor Cells, Cultured

Substances

Ceramides
Diethylamines
Fluorine Compounds
Fluorine
diethylaminosulfur trifluoride