Abstract
An efficient enantioselective synthesis of sn-2-aminooxy (AO) analogues of lysophosphatidic acid (LPA) that possess palmitoyl and oleoyl acyl chains is presented. Both sn-2-AO LPA analogues are agonists for the LPA1, LPA2, and LPA4 G-protein-coupled receptors, but antagonists for the LPA3 receptor and inhibitors of autotaxin (ATX). Moreover, both analogues stimulate migration of intestinal epithelial cells in a scratch wound assay.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Animals
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CHO Cells
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Cell Line, Tumor
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Cell Movement / drug effects
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Cricetinae
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Cricetulus
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Lysophospholipids / chemical synthesis*
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Lysophospholipids / chemistry
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Lysophospholipids / pharmacology*
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Molecular Structure
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Multienzyme Complexes / antagonists & inhibitors
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Phosphodiesterase I / antagonists & inhibitors
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Phosphoric Diester Hydrolases
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Pyrophosphatases / antagonists & inhibitors
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Rats
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Receptors, Lysophosphatidic Acid / antagonists & inhibitors
Substances
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Lysophospholipids
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Multienzyme Complexes
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Receptors, Lysophosphatidic Acid
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Phosphoric Diester Hydrolases
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Phosphodiesterase I
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alkylglycerophosphoethanolamine phosphodiesterase
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Pyrophosphatases
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lysophosphatidic acid