Cyclopamine
Cyclopamine is a steroidal jerveratrum alkaloid found in Veratrum that binds Smo, inhibiting hedgehog (Shh) signaling pathways. Cyclopamine exhibits anticancer activity, decreases expression of Gli2 and Bcl-2, inhibiting proliferation and inducing apoptosis in adenoma cells and neuroblastoma cells. CYCLOPAMINE SOLUBILITY: Ethanol is the best cyclopamine solvent for biological use. A 2.8% solution (28 mg/mL) can be prepared by sonicating the cyclopamine in ethanol. Avoid over heating. Storage at -20 ºC is recommended. If cyclopamine crystallizes out of solution. Upon thawing, the mixture can be heated or sonicated again to redissolve the cyclopamine. Methanol and DMSO can also be used as cyclopamine solvents, but solubility in methanol is much less (0.7 mg/mL). Substantial heating is again needed to achieve solution with methanol or DMSO.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18854375
| Cas No. |
4449-51-8 |
|---|---|
| Purity |
≥98% |
| Formula |
C27H41NO2 |
| Formula Wt. |
411.62 |
| Chemical Name |
Spiro(9H-benzo(a)fluorene-9,2(3H)-furo(3,2-b)pyridin)-3-ol, 1,2,3,3a,4,4,5,6,6,6a,6b,7,7,7a,8,11,11a,11b-octadecahydro-3,6,10,11b-tetramethyl-, (2R,3S,3R,3aS,6S,6aS,6bS,7aR,11aS,11bR)- |
| IUPAC Name |
(3S,3R,3aS,6S,6aS,6bS,7aR,9R,11aS,11bR)-3,6,10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol |
| Synonym |
11-Deoxyjervine; 11-Deoxojervine; HSDB 3505. |
| Melting Point |
212-215°C |
| Solubility |
Soluble in ethanol (≥20 mg/mL, methanol (0.7 mg/mL). Soluble in DMSO & insoluble in water. |
| Appearance |
White Crystalline Solid |
Song M, Ou X, Xiao C, et al. Hedgehog signaling inhibitor cyclopamine induces apoptosis by decreasing Gli2 and Bcl2 expression in human salivary pleomorphic adenoma cells. Biomed Rep. 2013 Mar;1(2):325-329. PMID: 24648943.
Xu L, Wang X, Wan J, et al. Sonic Hedgehog pathway is essential for neuroblastoma cell proliferation and tumor growth. Mol Cell Biochem. 2012 May;364(1-2):235-41. PMID: 22350753.
Stanton BZ, Peng LF. Small-molecule modulators of the Sonic Hedgehog signaling pathway. Mol Biosyst. 2010 Jan;6(1):44-54. PMID: 20024066.
