Palmitoyl 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 LPA.{14910} Palmitoyl 3-ccPA is a cyclic LPA analog that contains the 16:0 fatty acid, palmitate, 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 (81.9%) or LPA (98.9%) without affecting proliferation.{14910} 3-ccPA 16:0, at 0.1-25 ?M, significantly inhibits autotaxin,{14911,17450} an enzyme that is important in cancer cell survival, growth, migration, invasion and metastasis.