Potent platelet stimulating activity of enantiomers of acetyl glyceryl ether phosphorylcholine and its methoxy analogues

Donald J. Hanahan, P. G. Munder, Kiyoshi Satouchi, Linda McManus, R. Neal Pinckard

Research output: Contribution to journalArticle

73 Scopus citations

Abstract

Surprisingly, the sn-1 configuration of 1-0-hexadecyl-2-acetyl-glycerylphosphorylcholine showed significant activity, 3.22 × 10-9 M, when compared to the sn-3 enantiomer, 2.92 × 10-10 M and a racemic mixture with a value of 7.2 × 10-10 M. A methoxy substitution at the C-1 or C-2 position of octadecyl glycerylphosphorylcholine gave a derivative with high biological activity for stimulating serotonin release from rabbit platelets. A 1-0-dodecyl-2-methoxy analogue showed very low activity; also, a comparable series of 0-benzyl derivatives were inactive. Examination of 1-0-hexadecyl, 1-0-octadecyl- or 1-0-dodecyl-2-acetyl-sn-glyceryl-3-phosphorylcholine showed that the hexadecyl compound had three times the biological activity of the octadecyl and five times that of the dodecyl.

Original languageEnglish (US)
Pages (from-to)183-188
Number of pages6
JournalBiochemical and Biophysical Research Communications
Volume99
Issue number1
DOIs
StatePublished - Mar 16 1981
Externally publishedYes

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology
  • Cell Biology

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