Purmorphamine

Cayman Chemical Item Number 10009634

(CAS 483367-10-8)

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Description

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

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. Cell Biol Int 29(7) 537-541 (2005).

3. Wu, X., Walker, J., Zhang, J., et al. Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway. Chem Biol 11 1229-1238 (2004).

4. Sinha, S., and Chen, J.K. Purmorphamine activates the hedgehog pathway by targeting smoothened. Nat Chem Biol 2(1) 29-30 (2006).

Formal Name 9-​cyclohexyl-​N-​[4-​(morpholinyl)phenyl]-​2-​(1-​naphthalenyloxy)-​9H-​purin-​6-​amine
CAS Number 483367-10-8
Molecular Formula C31H32N6O2
Formula Weight 520.6
Formulation A crystalline solid
Purity ≥98%
λmax 221, 316 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O1CCN(CC1)​c1ccc(cc1)​Nc1nc(Oc2cccc3ccccc23)​nc2c1ncn2C1CCCCC1
InCHI Code
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​1S/C31H32N6O2/c1-2-9-25(10-3-1)​37-21-32-28-29(33-23-13-15-24(16-14-23)​36-17-19-38-20-18-36)​34-31(35-30(28)​37)​39-27-12-6-8-22-7-4-5-11-26(22)​27/h4-8,11-16,21,25H,1-3,9-10,17-20H2,(H,33,34,35)​
InCHI Key
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FYBHCRQFSFYWPY-UHFFFAOYSA-N

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Purmorphamine is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $22.00 $0.00
5 mg $99.00 $0.00
10 mg $176.00 $0.00
25 mg $385.00 $0.00
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