Enantioselective Responses to a Phosphorothioate Analogue of Lysophosphatidic Acid with LPA3 Receptor-Selective Agonist Activity

Lian Qian, Yong Xu, Yutaka Hasegawa, Junken Aoki, Gordon Mills, Glenn D. Prestwich

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

The metabolically stabilized LPA analogue, 1-oleoyl-2-O-methyl-rac-glycerophosphothioate (OMPT), is a potent agonist for the LPA3 G-protein-coupled receptor. A new enantiospecific synthesis of both (2R)-OMPT and (2S)-OMPT is described. Calcium release assays in both LPA3-transfected insect Sf9 and rat hepatoma Rh7777 cells showed that (2S)-OMPT was 5- to 20-fold more active than (2R)-OMPT. Similar results were found for calcium release, MAPK and Akt activation, and IL-6 release in human OVCAR3 ovarian cancer cells.

Original languageEnglish (US)
Pages (from-to)5575-5578
Number of pages4
JournalJournal of Medicinal Chemistry
Volume46
Issue number26
DOIs
StatePublished - Dec 18 2003
Externally publishedYes

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Lysophosphatidic Acid Receptors
Calcium
G-Protein-Coupled Receptors
Ovarian Neoplasms
Insects
Rats
Hepatocellular Carcinoma
Interleukin-6
Assays
Chemical activation
Cells
lysophosphatidic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Enantioselective Responses to a Phosphorothioate Analogue of Lysophosphatidic Acid with LPA3 Receptor-Selective Agonist Activity. / Qian, Lian; Xu, Yong; Hasegawa, Yutaka; Aoki, Junken; Mills, Gordon; Prestwich, Glenn D.

In: Journal of Medicinal Chemistry, Vol. 46, No. 26, 18.12.2003, p. 5575-5578.

Research output: Contribution to journalArticle

Qian, Lian ; Xu, Yong ; Hasegawa, Yutaka ; Aoki, Junken ; Mills, Gordon ; Prestwich, Glenn D. / Enantioselective Responses to a Phosphorothioate Analogue of Lysophosphatidic Acid with LPA3 Receptor-Selective Agonist Activity. In: Journal of Medicinal Chemistry. 2003 ; Vol. 46, No. 26. pp. 5575-5578.
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