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

Donald J. Hanahan, P. G. Munder, Kiyoshi Satouchi, Linda M Mcmanus, R. N Pinckard

Research output: Contribution to journalArticle

73 Citations (Scopus)

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

Fingerprint

Glycerylphosphorylcholine
Enantiomers
Platelet Activating Factor
Platelets
Bioactivity
Blood Platelets
Derivatives
Phosphorylcholine
Serotonin
Substitution reactions
Rabbits

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

Potent platelet stimulating activity of enantiomers of acetyl glyceryl ether phosphorylcholine and its methoxy analogues. / Hanahan, Donald J.; Munder, P. G.; Satouchi, Kiyoshi; Mcmanus, Linda M; Pinckard, R. N.

In: Biochemical and Biophysical Research Communications, Vol. 99, No. 1, 16.03.1981, p. 183-188.

Research output: Contribution to journalArticle

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AU - Pinckard, R. N

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AB - 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.

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