详情描述
Cyclopamine, also known as 11-deoxojervine, is a naturally occurring chemical that belongs to the group of steroidal jerveratrum alkaloids. It is a teratogen isolated from the corn lily (Veratrum californicum) that causes usually fatal birth defects. It can prevent the fetal brain from dividing into two lobes (holoprosencephaly) and cause the development of a single eye (cyclopia). It does so by inhibiting the hedgehog signaling pathway (Hh). Cyclopamine is useful in studying the role of Hh in normal development, and as a potential treatment for certain cancers in which Hh is overexpressed. Cyclopamine was named for one-eyed lambs which were born to sheep which grazed on wild corn lily at a farm in Idaho.
Product information
CAS Number: 4449-51-8
Molecular Weight: 411.62
Formula: C27H41NO2
Chemical Name: (2'R,3S,3'R,3a'S,6aS,6bS,6'S,7a'R,11aS,11bR)-3',6',10,11b-tetramethyl-1,2,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-3-ol
Smiles: C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC2[C@H]1CC[C@]1(O[C@@H]3C[C@H](C)CN[C@H]3[C@H]1C)C=2C
InChiKey: QASFUMOKHFSJGL-LAFRSMQTSA-N
InChi: InChI=1S/C27H41NO2/c1-15-11-24-25(28-14-15)17(3)27(30-24)10-8-20-21-6-5-18-12-19(29)7-9-26(18,4)23(21)13-22(20)16(27)2/h5,15,17,19-21,23-25,28-29H,6-14H2,1-4H3/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-/m0/s1
Technical Data
Appearance: Solid Power.
Purity: ≥98% (or refer to the Certificate of Analysis)
Solubility: DMSO up to 20 mM
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis
Storage Condition: Dry, dark and -20 oC for 1 year or refer to the Certificate of Analysis.
Shelf Life: ≥360 days if stored properly.
Stock Solution Storage: 0 - 4 oC for 1 month or refer to the Certificate of Analysis.
Drug Formulation: To be determined.
HS Tariff Code: 382200
How to use
In Vitro:
Cyclopamine was used at 3 µM in vitro and in cellular assays.
In Vivo:
Cyclopamine was administered at 50 mg/kg by subcutaneous injection once per day in tumor xenograft mouse model.
References:
- Chen JK, et al. Inhibition of Hedgehog signaling by direct binding of cyclopamine to Smoothened. (2002) Genes Dev. 16(21):2743-8.
- Scott MP. Cancer: a twist in a hedgehog's tale. (2003) Nature. 425(6960):780-2.
- Jiang J, et al. Hedgehog signaling in development and cancer. (2008) Dev Cell. 15(6):801-12.
Products are for research use only. Not for human use.