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C4116

Sigma-Aldrich

Cyclopamine hydrate

≥98% (HPLC), solid, Hedgehog signaling pathway inhibitor

Synonym(s):

11-deoxojervine hydrate

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About This Item

Empirical Formula (Hill Notation):
C27H41NO2 · xH2O
CAS Number:
Molecular Weight:
411.62 (anhydrous basis)
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.77

product name

Cyclopamine hydrate, ≥98% (HPLC)

Quality Level

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: soluble ≥5 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

O.C[C@@H]1CN[C@H]2[C@@H](C)[C@@]3(CC[C@H]4[C@@H]5CC=C6C[C@@H](O)CC[C@]6(C)[C@H]5CC4=C3C)O[C@@H]2C1

InChI

1S/C27H41NO2.H2O/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;1H2/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-;/m0./s1

InChI key

KDAGJRDPNXDDSB-HBYCUIHISA-N

Gene Information

human ... EBP(10682)

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General description

Cyclopamine is a steroidal alkaloid, extracted from Veratrum californicum. It prevents tumor cell growth and invasiveness in vitro and in vivo.

Application

Cyclopamine hydrate has been used:
  • as a sonic hedgehog (Shh) inhibitor in various experiments
  • to explore the effects of stress stimulation on the proliferation and differentiation of fibrochondrocytes
  • to study its influence on ocular vessel patterning

Biochem/physiol Actions

Cyclopamine is a Hedgehog signaling pathway inhibitor; inhibits the growth of medulloblastoma cells.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Ectodysplasin A regulates epithelial barrier function through sonic hedgehog signalling pathway
Li S, et al.
Journal of Cellular and Molecular Medicine, 22(1), 230-240 (2018)
Regulatory Mechanisms of the Ihh/PTHrP Signaling Pathway in Fibrochondrocytes in Entheses of Pig Achilles Tendon
Han X, et al.
Stem Cells International, 2016 (2016)
Cyclopamine: from cyclops lambs to cancer treatment
Lee ST, et al.
Journal of Agricultural and Food Chemistry, 62(30), 7355-7362 (2014)
Introduction to Cancer Metastasis (2016)
Loss of pancreas upon activated Wnt signaling is concomitant with emergence of gastrointestinal identity
Munoz-Bravo JL, et al
Testing, 11(10), e0164714-e0164714 (2016)

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