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239803

Sigma-Aldrich

Cyclopamine

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

Synonym(s):

Cyclopamine, V. californicum

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About This Item

Empirical Formula (Hill Notation):
C27H41NO2
CAS Number:
4449-51-8
Molecular Weight:
411.62
MDL number:
MFCD09878269
UNSPSC Code:
12352116
NACRES:
NA.77

product name

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 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

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

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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