Cyclopamine
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CYCLOPAMINE

Cyclopamine
CYCLOPAMINE Structure
CYCLOPAMINE
  • CAS No.4449-51-8
  • Chemical Name:CYCLOPAMINE
  • CBNumber:CB7677669
  • Molecular Formula:C27H41NO2
  • Formula Weight:411.62
  • MOL File:4449-51-8.mol
CYCLOPAMINE Property
  • Melting point: :236-238°C
  • Boiling point: :531.29°C (rough estimate)
  • Density  :1.0274 (rough estimate)
  • refractive index  :1.6400 (estimate)
  • storage temp.  :Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
  • solubility  :DMSO: soluble
  • form  :solid
  • pka :15.05±0.70(Predicted)
  • Stability: :Store in Freezer at - 20°C
  • EWG's Food Scores :1
  • FDA UNII :ZH658AJ192
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal word
  • Hazard statements H341-H361
  • Precautionary statements P201-P202-P280-P308+P313-P405-P501a
CYCLOPAMINE Price More Price(8)
  • Brand: Sigma-Aldrich
  • Product number: 239803
  • Product name : Cyclopamine, V. californicum - CAS 4449-51-8 - Calbiochem
  • Purity: 
  • Packaging: 1mg
  • Price: $169
  • Updated: 2020/08/18
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: PHL82510
  • Product name : Cyclopamine
  • Purity: phyproof Reference Substance
  • Packaging: 10mg
  • Price: $491.4
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Alfa Aesar
  • Product number: J61528
  • Product name : Cyclopamine, 99%
  • Purity: 
  • Packaging: 50mg
  • Price: $439
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Alfa Aesar
  • Product number: J61528
  • Product name : Cyclopamine, 99%
  • Purity: 
  • Packaging: 25mg
  • Price: $256
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Cayman Chemical
  • Product number: 11321
  • Product name : Cyclopamine
  • Purity: ≥95%
  • Packaging: 1mg
  • Price: $18
  • Updated: 2021/03/22
  • Buy: Buy

CYCLOPAMINE Chemical Properties,Usage,Production

  • 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.
  • Chemical Properties White Crystalline Solid
  • 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
  • Uses Cyclopamine antibacterial properties. Cyclopamine demonstrates teratogenic properties and has been shown to reverse effects of oncogenic mutations in Smoothened and Patched.
  • 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).
CYCLOPAMINE Preparation Products And Raw materials
Raw materials
Preparation Products
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4449-51-8, CYCLOPAMINERelated Search:
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  • 11-DEOXYJERVINE
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  • alkaloidv
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  • CYCLOPAMINE(RG)
  • Cyclopamine, 98%, from Veratrum californicum Durand
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  • Cyclopamine, 98%, from Veratrum californicim
  • Cyclopamine 4449-51-8
  • (2'R,3S,3'R,3a'S,6aS,6bS,6'S,7a'R,11aS,11bR)-3',6',10,11b-tetramethyl-1,2,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-3-ol
  • CYCLOPAMINE USP/EP/BP
  • 4449-51-8
  • C27H41NO2
  • Inhibitors
  • antibiotic
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Steroids
  • Lipid signaling