A purine derivative
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Reversine

Item No. 10004412

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N6-cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-9H-purine-2,6-diamine
CAS Number
656820-32-5
Molecular Formula
C21H27N7O
Formula Weight
393.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2) (1:8): 0.5 mg/mlDMSO: 10 mg/ml
λmax
283 nm
SMILES
C1CCC(CC1)Nc1nc(Nc2ccc(cc2)N2CCOCC2)nc2[nH]cnc12
InChi Code
InChI=1S/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27)
InChi Key
ZFLJHSQHILSNCM-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $40

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    5 mg

    $171

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    10 mg

    $302

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    25 mg

    $655

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    Product Description

    Reversine is a 2,6-disubstituted purine derivative that was originally found to induce dedifferentiation of C2C12 culture myoblast cells into stem cell progenitors when used at a concentration of 5 µM for four days.1 Depending on cell type, reversine promotes either differentiation or dedifferentiation. For example, in NT2 neuronal and HL-60 human promyelocytic leukemia cells, it induces differentiation.2 It inhibits the Aurora A, B, and C kinases with IC50 values of 98-876 nM and acts as an antagonist at the adenosine A3 receptor with a Ki value of 0.66 µM.2,3,4 Reversine is also used for studies of chromosome segregation. It inhibits the mitotic spindle checkpoint enzyme MPS1 with IC50 values of 6 and 2.8 nM for its kinase domain and full-length version, respectively).4 Reversine induces autophagy in WRO human follicular thyroid cancer cells and decreases Akt/mTOR signaling.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, S., Zhang, Q., Wu, X., et al. Dedifferentiation of lineage-committed cells by a small molecule. J. Am. Chem. Soc. 126(2), 410-411 (2004).

    2. D'Alise, A.M., Amabile, G., Iovino, M., et al. Reversine, a novel Aurora kinases inhibitor, inhibits colony formation of human acute myeloid leukemia cells. Mol. Cancer Ther. 7(5), 1140-1149 (2008).

    3. Perreira, M., Jiang, J.K., Klutz, A.M., et al. "Reversine" and its 2-substituted adenine derivatives as potent and selective A3 adenosine receptor antagonists. J. Med. Chem. 48(15), 4910-4918 (2005).

    4. Santaguida, S., Tighe, A., D'Alise, A.M., et al. Dissecting the role of MPS1 in chromosome biorientation and the spindle checkpoint through the small molecule inhibitor reversine. J. Cell. Biol. 190(1), 73-87 (2010).

    5. Lu, C.-H., Liu, Y.-W., Hua, S.-C., et al. Autophagy induction of reversine on human follicular thyroid cancer cells. Biomed. Pharmacother. 66(8), 642-647 (2012).

    Product Citations

    Lu, C.-H., Liu, Y.-W., Hua, S.-C., et al. Autophagy induction of reversine on human follicular thyroid cancer cells. Biomed. Pharmacother. 66(8), 642-647 (2012).