Formulation: A solution in chloroform
Formal Name: (2-hydroxy-2-oxido-1,2-oxaphospholan-5-yl)methyl ester-9Z-9Cl-9-hexadecenoic acid
Purity: ≥95%
Formula Markup: C20H37O5P
Formula Weight: 388,5
Shelf life (days): 365
CAS Number: 910228-13-6
Notes: 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} 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.{14910} 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.{14910} 3-ccPA 16:1 significantly inhibits autotaxin (IC50 = 620 nM),{14911} 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.{14911}
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