04449
O-(Octadecylphosphoryl)-cholin
≥98% (TLC)
Synonym(e):
Octadecylphosphocholin, Phosphocholin-octadecylester
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Empirische Formel (Hill-System):
C23H50NO4P
CAS-Nummer:
Molekulargewicht:
435.62
PubChem Substance ID:
UNSPSC Code:
12352211
Beilstein/REAXYS Number:
3694312
MDL number:
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Unterstützung erhaltenProduktname
O-(Octadecylphosphoryl)-cholin, ≥98% (TLC)
SMILES string
CCCCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C
InChI
1S/C23H50NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-27-29(25,26)28-23-21-24(2,3)4/h5-23H2,1-4H3
InChI key
ZBNJXSZNWZUYCI-UHFFFAOYSA-N
assay
≥98% (TLC)
lipid type
phospholipids
storage temp.
−20°C
Application
Antitumor phospholipid, induces apoptosis in three human leukemic cell lines.
Biochem/physiol Actions
C18-phosphocholine was the most potent alkylphosphocholine tested in inhibiting phosphatidylcholine biosynthesis. The effect is mediated by interrupting the translocation of the rate-limiting enzyme, CTP:phosphocholine cytidylyltransferase, to membranes, where it is active.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Lagerklasse
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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V Brochez et al.
Lipids, 34(5), 511-516 (1999-06-24)
The determination of cellular content of octadecylphosphocholine (D-19391) and hexadecylphosphocholine (HePC, D-18506), two anticancer agents of the alkylphosphocholine group, using capillary gas chromatography is described. The compounds' cytotoxicity was first determined by the MTT [3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium] assay, being indicative for the
R Zeisig et al.
Anti-cancer drugs, 2(4), 411-417 (1991-08-01)
Hexadecylphosphocholine (HPC) and its analogs with a longer alkyl chain (C18 and C20) were examined for antineoplastic activity in the murine tumor models P388 leukemia, B 16 melanoma, the mammary carcinoma C3H and Ca 755, and the human MT-1 mammary
S M Konstantinov et al.
Acta tropica, 64(3-4), 145-154 (1997-04-15)
Tetradecylphosphocholine (TPC), hexadecylphosphocholine (HPC), hexadecylphospho(N-N-N-trimethyl)hexanolamine (HPC6), octadecylphosphocholine (OPC), and octadecyl-[2-(N-methylpiperidinio)ethyl]-phosphate (OMPEP) were investigated for antitrypanosomal activity in vitro and in vivo. OMPEP showed the best trypanocidal efficacy in vitro; it was superior to the model compound HPC and comparable to
J Kötting et al.
Cancer chemotherapy and pharmacology, 30(2), 105-112 (1992-01-01)
Hexadecylphosphocholine (HPC) and octadecylphosphocholine (OPC) show very potent antitumor activity against autochthonous methylnitrosourea-induced mammary carcinomas in rats. The longer-chain and unsaturated homologue erucylphosphocholine (EPC) forms lamellar structures rather than micelles, but nonetheless exhibits antineoplastic activity. Methylnitrosourea was used in the
S M Konstantinov et al.
Cancer chemotherapy and pharmacology, 41(3), 210-216 (1998-01-27)
Alkylphosphocholines (APC) represent a new group of ether-lipid-related compounds with remarkable activity against transformed cells in vitro and good tolerability in vivo. Their mechanism of action remains unknown. The aim of the present study was to investigate the effects of
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