MedKoo Cat#: 406133 Name: Purmorphamine CAS#: 483367-10-8 Chemical Formula: C31H32N6O2 Exact Mass: 520.25867 Molecular Weight: 520.62 Elemental Analysis: C, 71.52; H, 6.20; N, 16.14; O, 6.15
Synonym: Purmorphamine
IUPAC/Chemical Name: 9-cyclohexyl-N-(4-morpholinophenyl)-2-(naphthalen-1-yloxy)-9H-purin-6-amine
InChi Key: FYBHCRQFSFYWPY-UHFFFAOYSA-N
InChi Code: InChI=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)
SMILES Code: N1(C2CCCCC2)C=NC3=C(NC4=CC=C(N5CCOCC5)C=C4)N=C(OC6=C7C=CC=CC7=CC=C6)N=C13
Technical Data
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not soluble in water.
Shelf Life: >5 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
Harmonized System Code: 293490
Additional Information
References
1: Wöltje M, Böbel M, Heiland M, Beck-Broichsitter B, Al-Dam A, Gröbe A, Friedrich RE, Hanken H, Smeets R. Purmorphamine and oxysterols accelerate and promote osteogenic differentiation of mesenchymal stem cells in vitro. In Vivo. 2015 Mar-Apr;29(2):247-54. PubMed PMID: 25792653.
2: Faghihi F, Baghaban Eslaminejad M, Nekookar A, Najar M, Salekdeh GH. The effect of purmorphamine and sirolimus on osteogenic differentiation of human bone marrow-derived mesenchymal stem cells. Biomed Pharmacother. 2013 Feb;67(1):31-8. doi: 10.1016/j.biopha.2012.10.004. Epub 2012 Nov 16. PubMed PMID: 23228449.
3: Granéli C, Karlsson C, Lindahl A, Thomsen P. Virtual ligand-based screening reveals purmorphamine analogs with the capacity to induce the osteogenic differentiation of human mesenchymal stem cells. Cells Tissues Organs. 2013;197(2):89-102. doi: 10.1159/000342796. Epub 2012 Nov 10. PubMed PMID: 23147751.
4: Oliveira FS, Bellesini LS, Defino HL, da Silva Herrero CF, Beloti MM, Rosa AL. Hedgehog signaling and osteoblast gene expression are regulated by purmorphamine in human mesenchymal stem cells. J Cell Biochem. 2012 Jan;113(1):204-8. doi: 10.1002/jcb.23345. PubMed PMID: 21898541.
5: Gellynck K, Neel EA, Li H, Mardas N, Donos N, Buxton P, Young AM. Cell attachment and response to photocured, degradable bone adhesives containing tricalcium phosphate and purmorphamine. Acta Biomater. 2011 Jun;7(6):2672-7. doi: 10.1016/j.actbio.2011.02.033. Epub 2011 Feb 25. PubMed PMID: 21354477.
6: El-Akabawy G, Medina LM, Jeffries A, Price J, Modo M. Purmorphamine increases DARPP-32 differentiation in human striatal neural stem cells through the Hedgehog pathway. Stem Cells Dev. 2011 Nov;20(11):1873-87. doi: 10.1089/scd.2010.0282. Epub 2011 Apr 5. PubMed PMID: 21345011.
7: Lee SJ, Lee HK, Cho SY, Choi JK, Shin HK, Kwak EJ, Cho MR, Kim HR, Kim SR, Kim YM, Park KJ, Choi JK. Identification of osteogenic purmorphamine derivatives. Mol Cells. 2008 Oct 31;26(4):380-6. Epub 2008 Aug 12. PubMed PMID: 18695357.
8: Sinha S, Chen JK. Purmorphamine activates the Hedgehog pathway by targeting Smoothened. Nat Chem Biol. 2006 Jan;2(1):29-30. Epub 2005 Nov 20. PubMed PMID: 16408088.
9: Beloti MM, Bellesini LS, Rosa AL. Purmorphamine enhances osteogenic activity of human osteoblasts derived from bone marrow mesenchymal cells. Cell Biol Int. 2005 Jul;29(7):537-41. PubMed PMID: 15979909.
10: Beloti MM, Bellesini LS, Rosa AL. The effect of purmorphamine on osteoblast phenotype expression of human bone marrow mesenchymal cells cultured on titanium. Biomaterials. 2005 Jul;26(20):4245-8. PubMed PMID: 15683647.
11: Wu X, Walker J, Zhang J, Ding S, Schultz PG. Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway. Chem Biol. 2004 Sep;11(9):1229-38. PubMed PMID: 15380183.
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