Inhibitor of autotaxin
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Palmitoleoyl 3-carbacyclic Phosphatidic Acid

Item No. 10010298

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9Z-hexadecenoic acid, (2-hydroxy-2-oxido-1,2-oxaphospholan-5-yl)methyl ester
CAS Number
910228-13-6
Synonyms
  • 3-carbacyclic PA
  • 3-ccPA 16:1
Molecular Formula
C20H37O5P
Formula Weight
388.5
Purity
≥95%
Formulation
A 10 mg/ml solution in chloroform
Solubility(Learn about Variance in 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
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $54

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    1 mg

    $103

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    5 mg

    $432

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    10 mg

    $755

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    Product 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 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.3 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 3-ccPA 16:1 significantly inhibits autotaxin (IC50 = 620 nM), an enzyme that is important in cancer cell survival, growth, migration, invasion and metastasis.4 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.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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(6), 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(1), 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. The Journal of Biological Chemisty 281(32), 22786-22793 (2006).