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4449-51-8

Supplier Related Products Identification Chemical Properties Hazard Information Safety Data Questions And Answer

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Identification

Name
CYCLOPAMINE
CAS
4449-51-8
Synonyms
alkaloidv
CYCLOPAMINE
11-DEOXOJERVINE
11-DEOXYJERVINE
11-deoxo-jervin
CYCLOPAMINE(RG)
Cyclopamine, >=98%
17,23β-Epoxyveratraman-3β-ol
17β,23β-Epoxyveratraman-3β-ol
CyclopaMine (11-deoxojervine)
CyclopaMine, froM VeratruM californiciM
Cyclopamine hydrate,11-deoxojervine hydrate
(3b,23b)-17,23-Epoxy-11-deoxoveratraman-3-ol
17,23-epoxy-,(3-beta,23-beta)-veratraman-3-o
(2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-
Cyclopamine 11-Deoxojervine (3b,23b)-17,23-Epoxy-11-deoxoveratraman-3-ol
(3S,6AS,6bS,8aR,10S,12aS,13S,13aS,15aS,15bR)-10,13,14,15b-tetramethyl-1,2,3,4,6,6a,6b,7,7a,8a
(2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-Octadecahydro-3',6',10,11b-tetramethylspiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-3-ol
(2'R,3S,3'R,3'AS,6'S,6AS,6BS,7'AR,11AS,11BR)-1,2,3,3'A,4,4',5',6,6',6A,6B,7,7',7'A,8,11,11A,11B-OCTADECAHYDRO-3',6',10,11B-TETRAMETHYLSPIRO[9H-BENZO[A]FLUORENE-9,2'(3'H)-FURO[3,2-B]PYRIDIN]-3-OL
Spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-3-ol,1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3',6',10,11b-tetraMethyl-,(2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-
Molecular Formula
C27H41NO2
MDL Number
MFCD01735266
MOL File
4449-51-8.mol
Molecular Weight
411.62

Chemical Properties

Appearance
White Crystalline Solid
Melting point 
236-238°C
Boiling point 
531.29°C (rough estimate)
density 
1.0274 (rough estimate)
refractive index 
1.6400 (estimate)
storage temp. 
2-8°C

solubility 
DMSO: soluble

form 
solid

pka
15.05±0.70(Predicted)
Stability:
Store in Freezer at - 20°C

Hazard Information

Chemical Properties
White Crystalline Solid
Uses
Cyclopamine antibacterial properties. Cyclopamine demonstrates teratogenic properties and has been shown to reverse effects of oncogenic mutations in Smoothened and Patched.
Uses
Has antibacterial properties. Cyclopamine demonstrates teratogenic properties and has been shown to reverse effects of oncogenic mutations in Smoothened and Patched.1 Solubility: 1mg dissolves in 0.2ml DMSO with heating to approximately 70 degrees (ca. 12 mmol sol.) Solubility: 4mg dissolves in 1ml 95% Ethanol
Biological Activity
Inhibitor of hedgehog (Hh) signaling, likely via direct inhibition of Smoothened, the accessory protein to the putative Hh receptor Patched. Anti-cancer and teratogenic in vivo . Depletes stem-like cancer cells in glioblastoma and blocks tumor engraftment.
Anticancer Research
Cyclopamine is a natural compound that inhibits the Hedgehog signaling pathway.Cyclopamine targets Hedgehog by specifically hindering SMO activation.Cyclopamine therapy of murine medulloblastoma resulted in the inhibition ofproliferation, induction of neuronal differentiation, effective depletion of CSCs, andreduction of tumor burden in a mouse tumor allograft. Cyclopamine is effective inkilling of pancreatic, breast, and multiple myeloma CSCs. Cyclopamine incombination with gemcitabine inhibits metastatic spread and reduces primary tumorburden in pancreatic orthotopic xenografts. Mammosphere formation in breastcarcinoma and SC proliferation in multiple myeloma can be reduced by cyclopamine(Kawasaki et al. 2008). The HH ligand activation requires cholesterol at theircarboxyl ends, and 22-OH-cholesterol and 20-OH-cholesterol are reported toincrease the HH target gene expression, and this hypothesis of cholesterol-dependentHH signal transduction is investigated in M2-10B4 pluripotent mesenchymal stemcells. The mechanism underlying the positive regulation of HH signaling by theseoxidative species of cholesterol is not clear. However, this oxidative status ofcholesterol is altered by the endogenous ROS. Hence, the bioactive food componentsthat control the ROS levels can be important in regulating self-renewal and HHpathways (Kim et al. 2012). Cholecalciferol (vitamin D3, an isoform of vitamin D)is reported to be HH antagonist in vitro but not in vivo. Binding of cholecalciferol toSMO receptors results in the reduction of HH signaling in MDAMB231 andC3H/10 T1/2 fibroblast cells. 1 μM vitamin D3 shows more potent SMO inhibitoryaction than 10 μM cyclopamine in PTCH1-transfected C3H/10 T1/2 cells (Kimet al. 2012). Curcumin interferes with the Gli1 mRNA or Gli reporter activity andinhibits HH signaling in transgenic mouse prostate adenocarcinoma cells (Kimet al. 2012).

Safety Data

Hazard Codes 
Xi
Safety Statements 
22-24/25
WGK Germany 
3

RTECS 
GY0750000

HS Code 
29349990
Hazardous Substances Data
4449-51-8(Hazardous Substances Data)

Questions And Answer

Cyclopamine
cyclopamine is a  isosteroidal alkaloid isolated from Veratrum plant , it mainly exists in four kinds of liliaceous plants which include North America Veratrum californicum , Indian Cornlily and Veratrum grandiflorum , Fritillaria pallidiflora Schrenk ,it can be combined with the Smoothened (Smo) protein in Hedgehog signaling pathway , thereby inhibiting the protein activity. It was discovered in the 1960s because of its teratogenic effects , but later nineties studies show that cyclopamine is a hedgehog signaling pathway inhibitor, it has been demonstrated in Drosophila body, since the hedgehog signaling pathway mutations are associated with the pathogenesis of a variety of tumors , recent studies have found that cyclopamine have anti-tumor effects in the adult, which has been confirmed in experiments in vivo or in vitro about pancreatic cancer, bile duct cancer, ovarian cancer, liver cancer and others , but on its researches about gastric cancer cells,it has not been reported in the country . Currently cyclopamine as a potential anti-cancer drug in the world sets off a wave of research.
The above information is edited by the chemicalbook of Tian Ye.
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