An inhibitor of PTPs
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Isomer(s)
27964TAN 1364B
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RK-682 (calcium salt)

Item No. 19450

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5R)-4-hydroxy-5-(hydroxymethyl)-3-(1-oxohexadecyl)-2(5H)-furanone, calcium salt (2:1)
CAS Number
332131-32-5
Synonyms
  • CI-010
  • TAN 1364B
Molecular Formula
[C21H35O5]2 • Ca
Formula Weight
775.1
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C1C(C(CCCCCCCCCCCCCCC)=O)=C([O-])[C@@H](CO)O1.O=C2C(C(CCCCCCCCCCCCCCC)=O)=C([O-])[C@@H](CO)O2.[Ca+2]
InChi Code
InChI=1S/3C21H36O5.Ca/c3*1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(23)19-20(24)18(16-22)26-21(19)25;/h3*18,22,24H,2-16H2,1H3;/q;;;+2/p-3/t3*18-;/m111./s1
InChi Key
YVSMJCYMLTVSLF-AFZPLCFTSA-K
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    Product Description

    RK-682, a bioactive compound originally isolated from the fermentation of Streptomyces sp. 88-682, is an inhibitor of the PTPs.1 It inhibits the phosphorylation of CD45 and VHR with IC50 values of 54 and 2 µM, respectively, and arrests cell cycle progress at the G1/S transition.1 It is also reported to inhibit heparanase (IC50 = 17 µM), an endo-β-D-glucuronidase involved in tumor cell invasion and angiogenesis.2 RK-682 (calcium salt) is a less soluble version of the free acid.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hamaguchi, T., Sudo, T., and Osada, H. RK-682, a potent inhibitor of tyrosine phosphatase, arrested the mammalian cell cycle progression at G1phase. FEBS Lett. 372(1), 54-58 (1995).

    2. Ishida, K., Hirai, G., Murakami, K., et al. Structure-based design of a selective heparanase inhibitor as an antimetastatic agent. Mol. Cancer Ther. 3(9), 1069-1077 (2004).

    3. Sodeoka, M., Sampe, R., Kojima, S., et al. Asymmetric synthesis of a 3-acyltetronic acid derivative, RK-682, and formation of its calcium salt during silica gel column chromatography. Chem. Pharm. Bull. (Tokyo) 49(2), 206-212 (2001).