Halo lipids. 10. Synthesis and cytostatic activity of O-alkylglycerophospho-L-serine analogs.
The synthesis of O-alkylglycerophospho-L-serine analogs is described, which represent a new class of cytostatically active agents based on phospholipids. The new compounds were obtained by conversion of O-alkylglycerophosphoric ester analogs by means of phospholipase D and by condensing O-alkylglycerophosphoric acid analogs with protected L-serine followed by the removal of protective groups of the resulting intermediates. The structure of the O-alkylglycerophospho-L-serines was confirmed by fast atom bombardment mass spectrometry. The compounds were found to inhibit the growth of Ehrlich ascites tumor cells in vitro. Half maximum inhibition was observed at concentrations between 7 and 15 microM. For the 1-O-alkyl-2-methoxy glycerophosphoserine only a higher value (30 microM) was found. With most of the substances tested growth was completely inhibited at a concentration of 40 microM.
Brachwitz
H
H
Akademie der Wissenschaften der DDR.
Langen
P
P
Dube
G
G
Schildt
J
J
Paltauf
F
F
Hermetter
A
A
D000818:Animals; D002286:Carcinoma, Ehrlich Tumor / Q000188:drug therapy; D055598:Chemical Phenomena; D002621:Chemistry; D006219:Halogens; D006801:Humans; D013058:Mass Spectrometry / Q000379:methods; D010718:Phosphatidylserines / Q000138:chemical synthesis* / Q000494:pharmacology; D010739:Phospholipase D / Q000378:metabolism; D012694:Serine / Q000031:analogs & derivatives; D014407:Tumor Cells, Cultured
D006219:Halogens; D010718:Phosphatidylserines; D012694:Serine; D010739:Phospholipase D