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239803

Cyclopamine

Name: Cyclopamine
Brand: MM

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

别名:

Cyclopamine, V. californicum

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关于此项目

经验公式（希尔记法）:

C₂₇H₄₁NO₂

化学文摘社编号:

4449-51-8

分子量:

411.62

UNSPSC Code:

12352116

NACRES:

NA.77

MDL number:

MFCD09878269

Assay:

≥95% (HPLC)

Form:

solid

Storage condition:

OK to freeze, protect from light

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属性

产品名称

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

说明

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)

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pictograms

GHS06,GHS08

signalword

Danger

hcodes

H301,H360D

pcodes

P202 - P264 - P280 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

存储类别

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