Synthesis and apoptogenic activity of fluorinated ceramide and dihydroceramide analogues

被引:24
作者
De Jonghe, S
Van Overmeire, I
Gunst, J
De Bruyn, A
Hendrix, C
Van Calenbergh, S
Busson, R
De Keukeleire, D
Philippé, J
Herdewijn, P
机构
[1] Univ Ghent, Fac Pharmaceut Sci, Med Chem Lab, B-9000 Ghent, Belgium
[2] Ghent Univ Hosp, Lab Clin Biol, Dept Haematol, B-9000 Ghent, Belgium
[3] Katholieke Univ Leuven, Rega Inst, Med Chem Lab, B-3000 Louvain, Belgium
关键词
D O I
10.1016/S0960-894X(99)00553-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
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. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3159 / 3164
页数:6
相关论文
共 15 条
[1]   CERAMIDE SYNTHASE MEDIATES DAUNORUBICIN-INDUCED APOPTOSIS - AN ALTERNATIVE MECHANISM FOR GENERATING DEATH SIGNALS [J].
BOSE, R ;
VERHEIJ, M ;
HAIMOVITZFRIEDMAN, A ;
SCOTTO, K ;
FUKS, Z ;
KOLESNICK, R .
CELL, 1995, 82 (03) :405-414
[2]   Structure-activity relationship of short-chain sphingoid bases as inhibitors of sphingosine kinase [J].
De Jonghe, S ;
Van Overmeire, I ;
Poulton, S ;
Hendrix, C ;
Busson, R ;
Van Calenbergh, S ;
De Keukeleire, D ;
Spiegel, S ;
Herdewijn, P .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (21) :3175-3180
[3]   THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].
GARNER, P ;
PARK, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364
[4]   IONIZING-RADIATION ACTS ON CELLULAR MEMBRANES TO GENERATE CERAMIDE AND INITIATE APOPTOSIS [J].
HAIMOVITZFRIEDMAN, A ;
KAN, CC ;
EHLEITER, D ;
PERSAUD, RS ;
MCLOUGHLIN, M ;
FUKS, Z ;
KOLESNICK, RN .
JOURNAL OF EXPERIMENTAL MEDICINE, 1994, 180 (02) :525-535
[5]   SYNTHESIS OF D-ERYTHRO-SPHINGOSINE AND D-THREO-SPHINGOSINE DERIVATIVES FROM L-SERINE [J].
HEROLD, P .
HELVETICA CHIMICA ACTA, 1988, 71 (02) :354-362
[6]   THE SPHINGOMYELIN PATHWAY IN TUMOR-NECROSIS-FACTOR AND INTERLEUKIN-1 SIGNALING [J].
KOLESNICK, R ;
GOLDE, DW .
CELL, 1994, 77 (03) :325-328
[7]   ANNEXIN-V FOR FLOW CYTOMETRIC DETECTION OF PHOSPHATIDYLSERINE EXPRESSION ON B-CELLS UNDERGOING APOPTOSIS [J].
KOOPMAN, G ;
REUTELINGSPERGER, CPM ;
KUIJTEN, GAM ;
KEEHNEN, RMJ ;
PALS, ST ;
VANOERS, MHJ .
BLOOD, 1994, 84 (05) :1415-1420
[8]   SYNTHESIS OF FLUORINE-CONTAINING ISOSTERES OF SPHINGOSINE AS INACTIVATORS OF PROTEIN KINASE-C [J].
KOZIKOWSKI, AP ;
WU, JP .
TETRAHEDRON LETTERS, 1990, 31 (30) :4309-4312
[9]   Signal transduction of stress via ceramide [J].
Mathias, S ;
Peña, LA ;
Kolesnick, RN .
BIOCHEMICAL JOURNAL, 1998, 335 :465-480
[10]   NEW FLUORINATING REAGENTS - DIALKYLAMINOSULFUR FLUORIDES [J].
MIDDLETON, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (05) :574-578