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Oleoyl 3-carbacyclic Phosphatidic Acid Exclusive

Cayman Chemical Item Number 10010299

3-ccPA 18:1

Oleoyl 3-carbacyclic Phosphatidic Acid

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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.1,2 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).3 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.3 At 25 μM, 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.3 3-ccPA 18:1, at 0.1-1.0 μM, significantly inhibits autotaxin,4,5 an enzyme that is important in cancer cell survival, growth, migration, invasion, and metastasis.

1 Kobayashi, T., Tanaka-Ishii, R., Taguchi, R., et al. Existence of a bioactive lipid, cyclic phosphatidic acid, bound to human serum albumin. Life Sci 65(21) 2185-2191 (1999).

2 Mukai, M., Imamura, F., Ayaki, M., et al. Inhibition of tumor invasion and metastasis by a novel lysophosphatidic acid (cyclic LPA). Int J Cancer 81 918-922 (1999).

3 Uchiyama, A., Mukai, M., Fujiwara, Y., et al. Inhibition of transcellular tumor cell migration and metastasis by novel carba-derivatives of cyclic phosphatidic acid. Biochim Biophys Acta 1771 103-112 (2007).

4 Baker, D.L., Fujiwara, Y., Pigg, K.R., et al. Carba analogs of cyclic phosphatidic acid are selective inhibitors of autotaxin and cancer cell invasion and metastasis. J Biol Chem 281(32) 22786-22793 (2006).

5 Prestwich, G.D., Gajewiak, J., Zhang, H., et al. Phosphatase-resistant analogues of lysophosphatidic acid: Agonists promote healing, antagonists and autotaxin inhibitors treat cancer. Biochim Biophys Acta 1781 588-594 (2008).

Synonyms
  • 3-ccPA 18:1
Formal Name (2-​hydroxy-​2-​oxido-​1,​2-​oxaphospholan-​5-​yl)methyl ester-​9Z-​octadecenoic acid
Molecular Formula C22H41O5P
Formula Weight 416.5
Formulation A solution in chloroform
Purity ≥95%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCCCCC/C=C\CCCCCCCC(=O)​OCC1CCP(=O)​(O)​O1

Background Reading

Kobayashi, T., Tanaka-Ishii, R., Taguchi, R., et al. Existence of a bioactive lipid, cyclic phosphatidic acid, bound to human serum albumin. Life Sci 65(21) 2185-2191 (1999).

Prestwich, G.D., Gajewiak, J., Zhang, H., et al. Phosphatase-resistant analogues of lysophosphatidic acid: Agonists promote healing, antagonists and autotaxin inhibitors treat cancer. Biochim Biophys Acta 1781 588-594 (2008).

Xu, Y., Jiang, G., Tsukahara, R., et al. Phosphonothioate and fluoromethylene phosphonate analogues of cyclic phosphatidic acid: Novel antagonists of lysophosphatidic acid receptors. J Med Chem 49 5309-5315 (2006).

Ory, J.J., and Banaszak, L.J. Studies of the ligand binding reaction of adipocyte lipid binding protein using the fluorescent probe 1,8-anilinonaphthalene-8-sulfonate. Biophys J 77 1107-1116 (1999).

Baker, D.L., Fujiwara, Y., Pigg, K.R., et al. Carba analogs of cyclic phosphatidic acid are selective inhibitors of autotaxin and cancer cell invasion and metastasis. J Biol Chem 281(32) 22786-22793 (2006).

Uchiyama, A., Mukai, M., Fujiwara, Y., et al. Inhibition of transcellular tumor cell migration and metastasis by novel carba-derivatives of cyclic phosphatidic acid. Biochim Biophys Acta 1771 103-112 (2007).

Mukai, M., Imamura, F., Ayaki, M., et al. Inhibition of tumor invasion and metastasis by a novel lysophosphatidic acid (cyclic LPA). Int J Cancer 81 918-922 (1999).

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Size Price Quantity Subtotal
500 µg $61.00 $0.00
1 mg $116.00 $0.00
5 mg $488.00 $0.00
10 mg $854.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-25. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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