Cyclopamine

AdipoGen Life Sciences
Product Code: AG-CN2-0028
CodeSizePrice
AG-CN2-0028-M0011 mg£35.00
Quantity:
AG-CN2-0028-M0055 mg£60.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
11-Deoxyjervine; 11-Deoxojervine; HSDB 3505
Appearance:
White to off-white solid.
CAS:
4449-51-8
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07,GHS08
Handling Advice:
Protect from light.
Hazards:
H302, H319, H361d
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
InChiKey:
QASFUMOKHFSJGL-LAFRSMQTSA-N
Long Description:
Chemical. CAS: 4449-51-8. Formula: C27H41NO2. MW: 411.6. Isolated from Veratrum californicum. Cell permeable steroidal alkaloid. Specific sonic hedgehog (Shh) signaling pathway inhibitor. Directly interacts/inhibits Smo (smoothened). Teratogenic and antitumor compound. Inhibits tumor cell growth and progression. Shows selective activity against Shh-dependent tumors. Blocks abnormal cell growth associated with oncogenic mutations of Ptch and Smo in fibroblasts. Arrests cell cycle at G0/G1. Apoptosis inducer.
MDL:
MFCD09878269
Molecular Formula:
C27H41NO2
Molecular Weight:
411.6
Package Type:
Vial
Precautions:
P301, P312, P308, P313, P330
Product Description:
Cell permeable steroidal alkaloid. Specific sonic hedgehog (Shh) signaling pathway inhibitor. Directly interacts/inhibits Smo (smoothened) [1-4]. Teratogenic [1] and antitumor compound. Inhibits tumor cell growth and progression. Shows selective activity against Shh-dependent tumors [5-11]. Blocks abnormal cell growth associated with oncogenic mutations of Ptch and Smo in fibroblasts [2]. Arrests cell cycle at G0/G1 [6]. Apoptosis inducer [8].
Purity:
>98%
Signal word:
Warning
SMILES:
[H][C@@]12C[C@H](C)CN[C@@]1([H])[C@@H](C)[C@@]1(CC[C@]3([H])C(C[C@@]4([H])[C@@]3([H])CC=C3C[C@@H](O)CC[C@]43C)=C1C)O2
Solubility Chemicals:
Soluble in ethanol, methanol, DMF or DMSO. Insoluble in water.
Source / Host:
Isolated from Veratrum californicum.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C. Store solutions at -20°C in the dark.

References

The teratogenic Veratrum alkaloid cyclopamine inhibits sonic hedgehog signal transduction: J.P. Incardona, et al.; Development 125, 3553 (1998) | Pancreas development is promoted by cyclopamine, a hedgehog signaling inhibitor: S.K. Kim & D.A. Melton; PNAS 95, 13036 (1998) | Effects of oncogenic mutations in Smoothened and Patched can be reversed by cyclopamine: J. Taipale, et al; Nature 406, 1005 (2000) | Inhibition of Hedgehog signaling by direct binding of cyclopamine to Smoothened: J.K. Chen, et al.; Genes Dev. 16, 2743 (2002) | Hedgehog signalling in colorectal tumour cells: induction of apoptosis with cyclopamine treatment: D. Qualtrough, et al.; Int. J. Cancer 110, 831 (2004) | The hedgehog pathway inhibitor cyclopamine increases levels of p27, and decreases both expression of IGF-II and activation of Akt in PC-3 prostate cancer cells: R.J. Levitt, et al.; Cancer Lett. 255, 300 (2007) | Cyclopamine-mediated hedgehog pathway inhibition depletes stem-like cancer cells in glioblastoma: E.E. Bar, et al.; Stem Cells 25, 2524 (2007) | The hedgehog inhibitor cyclopamine induces apoptosis in leukemic cells in vitro: J. Warzecha, et al.; Leuk. Lymph. 49, 2383 (2008) | Cyclopamine inhibition of human breast cancer cell growth independent of Smoothened (Smo): X. Zhang, et al.; Breast Cancer Res. Treat. 115, 505 (2009) | Cyclopamine and hedgehog signaling: chemistry, biology, medical perspectives: P. Heretsch, et al.; Chem. Int. Ed. Engl. 49, 3418 (2010) (Review) | Targeting the hedgehog pathway: the development of cyclopamine and the development of anti-cancer drugs targeting the hedgehog pathway: A. Gould & S. Missailidis; Mini Rev. Med. Chem. 11, 200 (2011) (Review)

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