A P-glycoprotein inhibitor
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Piperafizine A

Item No. 19449

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-methyl-3Z,6Z-bis(phenylmethylene)-2,5-piperazinedione
CAS Number
130603-59-7
Molecular Formula
C19H16N2O2
Formula Weight
304.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: solubleWater: limited solubility
SMILES
O=C(/C(NC/1=O)=C/C2=CC=CC=C2)N(C)C1=C/C3=CC=CC=C3
InChi Code
InChI=1S/C19H16N2O2/c1-21-17(13-15-10-6-3-7-11-15)18(22)20-16(19(21)23)12-14-8-4-2-5-9-14/h2-13H,1H3,(H,20,22)/b16-12-,17-13-
InChi Key
DILBTCUXPAXMSM-MCOFMCJXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $294

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    5 mg

    $929

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    Product Description

    Piperafizine A is a natural methylated diketopiperazine first isolated from an actinomycete, Streptoverticillium.1 It potentiates the cytotoxicity of vincristine (Item No. 11764), an anti-cancer alkaloid known to be exported from cells by P-glycoprotein.1,2 Piperafizine A directs the intracellular accumulation of vincristine in cancer cells to a similar degree as verapamil (Item No. 14288), a P-glycoprotein inhibitor.3,4 The effects of piperafizine A on vincristine accumulation in cancer cells is dose-dependent over a range of 1 to 20 µg/ml.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kamei, H., Oka, M., Hamagishi, Y., et al. Piperafizines A and B, potentiators of cytotoxicity of vincristine. J. Antibiot. (Tokyo) 43(8), 1018-1020 (1990).

    2. van Tellingen, O., Buckle, T., Jonker, J.W., et al. P-glycoprotein and Mrp1 collectively protect the bone marrow from vincristine-induced toxicity in vivo. Br. J. Cancer 89(9), 1776-1782 (2003).

    3. Ogasawara, M., Hasegawa, M., Hamagishi, Y., et al. Potentiation of vincristine cytotoxicity by rubiginone B1 and piperafizine A in human Moser and K562 cells—mode of action. J. Antibiot. (Tokyo) 45(1), 129-132 (1992).

    4. Chan, H.S.L., Haddad, G., Thorner, P.S., et al. P-glycoprotein expression as a predictor of the outcome of therapy for neuroblastoma. New Engl. J. Med. 325(23), 1608-1614 (1991).