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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.

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)


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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Giuditta Guerrini et al.
Journal of cellular physiology, 233(12), 9799-9811 (2018-08-23)
Breast cancer (BC) relapse and metastasis are the leading cause of death and, together with drug resistance, keep mortality still high. The Hedgehog (Hh) pathway is expressed during embryogenesis, organogenesis and in adult tissue homeostasis and its aberrant activation is
Cyclopamine: from cyclops lambs to cancer treatment
Lee ST, et al.
Journal of Agricultural and Food Chemistry, 62(30), 7355-7362 (2014)
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)
Ocular vessel patterning in zebrafish is indirectly regulated by Hedgehog signaling
Weiss O, et al.
International Journal of Developmental Biology, 61(3-4-5), 277-284 (2017)

Articles

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Cancer stem cell media, spheroid plates and cancer stem cell markers to culture and characterize CSC populations.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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