C4116
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)
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
11 - Combustible Solids
wgk
WGK 3
ppe
Eyeshields, Gloves, type N95 (US)
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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)
Carlos Andrés Chacón-Martínez et al.
The EMBO journal, 36(2), 151-164 (2016-12-13)
Understanding how complex tissues are formed, maintained, and regenerated through local growth, differentiation, and remodeling requires knowledge on how single-cell behaviors are coordinated on the population level. The self-renewing hair follicle, maintained by a distinct stem cell population, represents an