Synthesis, pharmacology, and cell biology of sn-2-aminooxy analogues of lysophosphatidic acid

摘要

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 LPA(1), LPA(2), and LPA(4) G-protein-coupled receptors, but antagonists for the LPA(3) receptor and inhibitors of autotaxin (ATX). Moreover, both analogues stimulate migration of intestinal epithelial cells in a scratch wound assay.