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

doi:10.1016/0006-291X(81)91730-7

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 journal › Article › peer-review

74 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 language	English (US)
Pages (from-to)	183-188
Number of pages	6
Journal	Biochemical and Biophysical Research Communications
Volume	99
Issue number	1
DOIs	https://doi.org/10.1016/0006-291X(81)91730-7
State	Published - Mar 16 1981
Externally published	Yes

ASJC Scopus subject areas

Molecular Biology
Biophysics
Biochemistry
Cell Biology

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title = "Potent platelet stimulating activity of enantiomers of acetyl glyceryl ether phosphorylcholine and its methoxy analogues",

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.",

author = "Hanahan, {Donald J.} and Munder, {P. G.} and Kiyoshi Satouchi and Linda McManus and {Neal Pinckard}, R.",

note = "Funding Information: This study was supported by a grant, HL-2255503, from the National Institute of Heart, Lung and Blood. We wish to acknowledge the excellent technical assistance of Richard Castillo and Carol Lange.",

year = "1981",

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doi = "10.1016/0006-291X(81)91730-7",

language = "English (US)",

volume = "99",

pages = "183--188",

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T1 - Potent platelet stimulating activity of enantiomers of acetyl glyceryl ether phosphorylcholine and its methoxy analogues

AU - Hanahan, Donald J.

AU - Munder, P. G.

AU - Satouchi, Kiyoshi

AU - McManus, Linda

AU - Neal Pinckard, R.

N1 - Funding Information: This study was supported by a grant, HL-2255503, from the National Institute of Heart, Lung and Blood. We wish to acknowledge the excellent technical assistance of Richard Castillo and Carol Lange.

PY - 1981/3/16

Y1 - 1981/3/16

N2 - 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.

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

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