239803

Cyclopamine

from Veratrum californicum, ≥97% (HPLC), solid, Sonic Hedgehog signaling antagonist, Calbiochem^®

• Sinónimos: Cyclopamine, V. californicum
• Fórmula empírica (notación de Hill): C₂₇H₄₁NO₂
• Número CAS: 4449-51-8
• Peso molecular: 411.62
• UNSPSC Code: 12352116
• NACRES: NA.77
• MDL number: MFCD09878269
• Assay: ≥95% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Propiedades

• Nombre del producto: 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.
• Quality Segment: 100
• description: RTECS - GY0750000
• assay: ≥95% (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
• SMILES string: N1[C@@H]2[C@H](O[C@@]3([C@@H]2C)CC[C@H]4[C@H]5[C@@H]([C@]6(CC[C@@H](CC6=CC5)O)C)CC4=C3C)C[C@@H](C1)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

Descripción

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 can be used as a negative control. Also available as a 10 mM solution in Ethanol (Cat. No. 239806).

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.

Preparation Note

Ethanol stock solutions may require warming to achieve complete solubilization.

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

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

Información de seguridad

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H301,H360D
• pcodes: P202 - P264 - P280 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral - Repr. 1B
• Clase de almacenamiento: 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