Oleoyl 3-carbacyclic Phosphatidic Acid

Cyclic phosphatidic acids (cPAs) are naturally occurring analogs of lysophosphatidic acid (LPA) in which the sn-2 hydroxy group forms a 5-membered ring with the sn-3 phosphate.{17448,17449} Carba-derivatives of cPA (ccPA) are modified at the sn-2 (2-ccPA) or sn-3 (3-ccPA) linkage, preventing the opening of cPA to produce lysophosphatidic acid (LPA).{14910} Oleoyl 3-Carbacyclic Phosphatidic Acid (3-ccPA 18:1) is a cyclic LPA analog that contains the 18:1 fatty acid, oleate, at the sn-1 position of the glycerol backbone.{14910} At 25 ?M, it inhibits the transcellular migration of MM1 cells across mesothelial cell monolayers in response to fetal bovine serum (90.1%) or LPA (99.9%) without affecting proliferation.{14910} 3-ccPA 18:1, at 0.1-1.0 ?M, significantly inhibits autotaxin,{14911,17450} an enzyme that is important in cancer cell survival, growth, migration, invasion, and metastasis.