SYNTHESIS OF HEXADECYLPHOSPHO[METHYL-C-14]-CHOLINE

被引:20
作者
GEILEN, CC [1 ]
SAMSON, A [1 ]
WIEDER, T [1 ]
WILD, H [1 ]
REUTTER, W [1 ]
机构
[1] BAYER AG,CHEM SCI LABS PHARMA,W-5600 WUPPERTAL 1,GERMANY
关键词
HEXADECYLPHOSPHO[METHYL-C-14]-CHOLINE; PHOSPHOLIPID ANALOGS; ETHERLIPIDS;
D O I
10.1002/jlcr.2580311216
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Hexadecylphospho[methyl-C-14]-choline was synthesized in two steps from the tetra-n-butyl-ammonium salt of phosphoryl[methyl-C-14]-choline and 1-bromohexadecane, and purified by column chromatography on Silica gel. The total yield of the radioactive synthesis was 35%, whereas the total yield of the non-radioactive synthesis was 40%. Hexadecylphospho[methyl-C-14]-choline may serve as a useful tool for pharmacokinetic and biochemical studies of this new antitumor drug.
引用
收藏
页码:1071 / 1076
页数:6
相关论文
共 14 条
  • [1] EIBL H, 1967, LIEBIGS ANN CHEM, V709, P244
  • [2] HEXADECYLPHOSPHOCHOLINE - A NEW AND SELECTIVE ANTITUMOR DRUG
    EIBL, H
    UNGER, C
    [J]. CANCER TREATMENT REVIEWS, 1990, 17 (2-3) : 233 - 242
  • [3] A GENERAL SYNTHETIC METHOD FOR ENANTIOMERICALLY PURE ESTER AND ETHER LYSOPHOSPHOLIPIDS
    EIBL, H
    WOOLLEY, P
    [J]. CHEMISTRY AND PHYSICS OF LIPIDS, 1988, 47 (01) : 63 - 68
  • [4] FLEER EAM, 1986, SYNTHESIS APPLICATIO, P473
  • [5] THE PHOSPHOLIPID ANALOG, HEXADECYLPHOSPHOCHOLINE, INHIBITS PROTEIN-KINASE-C INVITRO AND ANTAGONIZES PHORBOL ESTERSTIMULATED CELL-PROLIFERATION
    GEILEN, CC
    HAASE, R
    BUCHNER, K
    WIEDER, T
    HUCHO, F
    REUTTER, W
    [J]. EUROPEAN JOURNAL OF CANCER, 1991, 27 (12) : 1650 - 1653
  • [6] GEILEN CC, 1992, J BIOL CHEM, V267, P6719
  • [7] THE PHOSPHOLIPID ANALOG HEXADECYLPHOSPHOCHOLINE INHIBITS PHOSPHATIDYLCHOLINE BIOSYNTHESIS IN MADIN-DARBY CANINE KIDNEY-CELLS
    HAASE, R
    WIEDER, T
    GEILEN, CC
    REUTTER, W
    [J]. FEBS LETTERS, 1991, 288 (1-2) : 129 - 132
  • [8] AN IMPROVED SYNTHESIS OF 6-(O-PHOSPHORYLCHOLINE)HYDROXYHEXANOIC ACID
    KNOPIK, P
    BRUZIK, KS
    STEC, WJ
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1991, 23 (02) : 214 - 216
  • [9] EFFECTS OF HEXADECYLPHOSPHOCHOLINE ON PROTEIN-KINASE-C AND TPA-INDUCED DIFFERENTIATION OF HL60 CELLS
    SHOJI, M
    RAYNOR, RL
    FLEER, EAM
    EIBL, H
    VOGLER, WR
    KUO, JF
    [J]. LIPIDS, 1991, 26 (02) : 145 - 149
  • [10] UBERALL F, 1991, CANCER RES, V51, P807