239803

Cyclopamine, V. californicum

Cyclopamine, V. californicum, CAS 4449-51-8, is a cell-permeable steroidal alkaloid & cholesterol mimic that specifically antagonizes Sonic Hedgehog signaling through direct interaction with Smo.

• Synonym(s): Cyclopamine, V. californicum
• Empirical Formula (Hill Notation): C₂₇H₄₁NO₂
• CAS Number: 4449-51-8
• Molecular Weight: 411.62
• MDL number: MFCD09878269
• UNSPSC Code: 12352116

Properties

• Quality Level: 100
• Assay: ≥97% (HPLC)
• form: solid
• potency: 20 nM IC₅₀
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: off-white
• solubility: DMF: 10 mg/mL; DMSO: 4 mg/mL; ethanol: 5 mg/mL
• shipped in: wet ice
• storage temp.: −20°C
• 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
• InChI key: QASFUMOKHFSJGL-LAFRSMQTSA-N

Description

General description

A cell-permeable steroidal alkaloid and cholesterol mimic that displays both teratogenic and antitumor activities. It disrupts cholesterol bio-synthesis and specifically antagonizes shh (Sonic Hedgehog) signaling pathway through direct interaction with Smo (smoothened), a distant relative of G-protein-coupled receptors. A valuable tool for studying the involvement of shh signaling in the development of various tumors. Tomatidine (Cat. No. 614350) can be used as a negative control. Also available as a 10 mM solution in Ethanol (Cat. No. 239806).

A cell-permeable, steroidal alkaloid and cholesterol mimic that displays both teratogenic and anti-tumor properties. Disrupts cholesterol biosynthesis and specifically antagonizes shh (Sonic Hedgehog) signaling through direct interaction with Smo (smoothened), a protein that is related to G-protein-coupled receptors. Useful for studying the involvement of shh signaling in the development of various tumors. Tomatidine (Cat. No. 614350) can be used as a negative control.

Cyclopamine, V. californicum, CAS 4449-51-8, is a cell-permeable steroidal alkaloid & cholesterol mimic that specifically antagonizes Sonic Hedgehog signaling through direct interaction with Smo.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Hh signaling in Shh-light2 assay

Product does not compete with ATP.

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Preparation Note

Ethanol stock solutions may require warming to achieve complete solubilization.

Reconstitution

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Berman, D.M., et al. 2003. Nature,425, 846.
Thayer, S.P., et al. 2003. Nature,425, 851.
Watkins, D.N., et al. 2003. Nature422, 313.
Chen, J.K., et al. 2002. Proc. Natl. Acad. Sci. USA99, 14071.
Berman, D.M., et al. 2002. Science297, 1559.
Taipale, J., et al. 2000. Nature406, 1005.
Kim, S.K., and Melton, D.A. 1998. Proc. Natl. Acad. Sci. USA95, 13036.
Cooper, M.K., et al. 1998. Science280, 1603.
Incardona, J.P., et al. 1998. Development125, 3553.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H301 - H360D
• Precautionary Statements: P202 - P264 - P280 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral - Repr. 1B
• Storage Class Code: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable