Palmitoleoyl 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. 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). Palmitoleoyl 3-carbacyclic phosphatidic acid (3-ccPA 16:1) is a cyclic LPA analog that contains the 16:1 fatty acid, palmitoleate, at the sn-1 position of the glycerol backbone. At 25 µM, it inhibits the transcellular migration of MM1 cells across mesothelial cell monolayers in response to fetal bovine serum (86.9%) or LPA (99.9%) without affecting proliferation. 3-ccPA 16:1 significantly inhibits autotaxin (IC50 = 620 nM), an enzyme that is important in cancer cell survival, growth, migration, invasion and metastasis. When delivered intraperitoneally, 3-ccPA 16:1 significantly reduces the number of lung metastases formed in mice injected with B16F10 melanoma cells in the tail vein.Formal Name: (2-hydroxy-2-oxido-1,2-oxaphospholan-5-yl)methyl ester-9Z-9Cl-9-hexadecenoic acid. CAS Number: 910228-13-6. Synonyms: 3-carbacyclic PA, 3-ccPA 16:1. Molecular Formula: C20H37O5P. Formula Weight: 388.5. Purity: >95%. Formulation: (Request formulation change), A solution in chloroform. Solubility: PBS (pH 7.2): 5 mg/ml. SMILES: CCCCCC/C=C\CCCCCCCC(=O)OCC1CCP(=O)(O)O1. InChi Code: InChI=1S/C20H37O5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(21)24-18-19-16-17-26(22,23)25-19/h7-8,19H,2-6,9-18H2,1H3,(H,22,23)/b8-7-. InChi Key: IAGUMCXYAAGWJD-FPLPWBNLSA-N. Side Chain Carbon Sum: 16:1.