Purmorphamine CAS 483367-10-8

Brand

BioReagent™

CAS Number

483367-10-8

Grade

Highly Purified

Molecular Formula

C₃₁H₃₂N₆O₂

Molecular Weight

520.62

EU Commodity Code

38220090

Shipping Temp

Blue Ice

Storage Temp

4°C

9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-9H-purin-6-amine

A 2,6,9-trisubstituted purine that promotes the differentiation of both human and murine mesenchymal progenitor cells into osteoblasts. It directly binds to and activates 7- transmembrane Smo receptor of the Hedgehog (Hh) signaling pathway.

Synonym

9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-9H-purin-6-amine

CAS No

483367-10-8

Molecular Formula

C₃₁H₃₂N₆O₂

Molecular Weight

520.62

Purity

~98%

Appearance

Light Tan to Light Brown Solid

Melting Point

>191°C (dec.)

Solubility

Chloroform (Slightly), DMSO (Slightly)

For long term storage, we suggest that purmorphamine be stored as supplied at -20°C. It should be stable for at least two years. Purmorphamine is supplied as a crystalline solid. A stock solution may be made by dissolving the purmorphamine in an organic solvent purged with an inert gas. Purmorphamine is soluble in organic solvents such as DMSO and dimethyl formamide (DMF). The solubility of purmorphamine in these solvents is approximately 10 and 20 mg/ml, respectively. Purmorphamine is sparingly soluble in aqueous buffers. For maximum solubility in aqueous buffers, purmorphamine should first be dissolved in DMF and then diluted with the aqueous buffer of choice. Purmorphamine has a solubility of approximately 0.25 mg/ml in a 1:2 solution of DMF:PBS (pH 7.2) using this method. We do not recommend storing the aqueous solution for more than one day. Small molecules that promote osteoblast differentiation might be useful as therapeutic agents for bone diseases such as osteoporosis. Purmorphamine is a 2,6,9-trisubstituted purine that promotes the differentiation of both human and mouse mesenchymal progenitor cells into osteoblasts.1,2 The EC50 value for differentiation of C3H10T1/2 cells based on alkaline phosphatase expression is 1 μM.1 Investigation into purmorphamine’s mechanism of action indicates that it directly binds to and activates the 7-transmembrane Smo receptor of the Hedgehog signaling pathway.3,4

References

1. Wu, X., Ding, Q., Gray, N.S., et al. A small molecule with osteogenesis-inducing activity in multipotent mesenchymal progenitor cells. J. Am. Chem. Soc. 124, 14520-14521 (2002).|2. Beloti, M.M., Bellesini, L.S., and Rosa, A.L. Purmorphamine enhances osteogenic activity of human osteoblasts derived from bone marrow mesenchymal cells. Journal of Cell Biology International 29(7), 537-541 (2005).|3. Wu, X., Walker, J., Zhang, J., et al. Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway. Chemistry & Biology 11, 1229-1238 (2004).|4. Sinha, S. and Chen, J.K. Purmorphamine activates the hedgehog pathway by targeting smoothened. Nature Chemical Biology 2(1), 29-30 (2006).

USBio References

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P9199-65 Purmorphamine CAS: 483367-10-8

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9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-9H-purin-6-amine

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