| Identification | Back Directory | [Name]
Palmitoyl 3-carbacyclic Phosphatidic Acid | [CAS]
476310-22-2 | [Synonyms]
LJNWYINJKCNEPA-UHFFFAOYSA-N
Palmitoyl 3-carbacyclic Phosphatidic Acid
Palmitoyl 3-carbacyclic Phosphatidic Acid Exclusive
Hexadecanoic acid, (2-hydroxy-2-oxido-1,2-oxaphospholan-5-yl)methyl ester | [Molecular Formula]
C20H39O5P | [MOL File]
476310-22-2.mol | [Molecular Weight]
390.49 |
| Hazard Information | Back Directory | [Description]
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 LPA. 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. At 25 μM, 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. 3-ccPA 16:0, at 0.1-25 μM, significantly inhibits autotaxin, an enzyme that is important in cancer cell survival, growth, migration, invasion and metastasis. | [Uses]
Palmitoyl 3-carbacyclic phosphatidic acid (HY-139061) is a palmitoylated Carba-like cyclophosphatidic acid and an analog of lysophosphatidic acid (LPA). Palmitoyl 3-carbacyclic phosphatidic acid has different functions from LPA and can inhibit the activation of RhoA and inhibit the migration of melanoma cells. Palmitoyl 3-carbacyclic phosphatidic acid effectively inhibited experimental lung metastasis and reduced the number of tumor nodules in a B16-F0 xenograft mouse model[1]. | [References]
[1] Uchiyama A, et al. Inhibition of transcellular tumor cell migration and metastasis by novel carba-derivatives of cyclic phosphatidic acid. Biochim Biophys Acta. 2007 Jan;1771(1):103-12. DOI:10.1016/j.bbalip.2006.10.001 |
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