Cyclopamine
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CYCLOPAMINE

Cyclopamine
Product Name
CYCLOPAMINE
CAS No.
4449-51-8
Chemical Name
CYCLOPAMINE
Synonyms
alkaloidv;CYCLOPAMINE;Compound T3525;11-DEOXOJERVINE;11-DEOXYJERVINE;11-deoxo-jervin;CYCLOPAMINE(RG);Cyclopamine 99+%;Cyclopamine, >=98%;Cyclopamine 4449-51-8
CBNumber
CB7677669
Molecular Formula
C27H41NO2
Formula Weight
411.62
MOL File
4449-51-8.mol
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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)
color 
White
Stability:
Store in Freezer at - 20°C
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
239803
Product name
Cyclopamine, V. californicum - CAS 4449-51-8 - Calbiochem
Packaging
1mg
Price
$216
Updated
2024/03/01
Sigma-Aldrich
Product number
PHL82510
Product name
Cyclopamine
Purity
phyproof Reference Substance
Packaging
10mg
Price
$606
Updated
2024/03/01
Alfa Aesar
Product number
J61528
Product name
Cyclopamine, 99%
Packaging
25mg
Price
$301
Updated
2024/03/01
Alfa Aesar
Product number
J61528
Product name
Cyclopamine, 99%
Packaging
50mg
Price
$441.65
Updated
2024/03/01
Cayman Chemical
Product number
11321
Product name
Cyclopamine
Purity
≥95%
Packaging
1mg
Price
$23
Updated
2024/03/01
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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.

Description

Cyclopamine is a natural steroidal alkaloid that inhibits signaling through the hedgehog pathway at the level of the pathway activator Smoothened. By altering gene expression in this signaling sequence, cyclopamine induces defects in morphogenesis, first observed in chicks and sheep as cyclopia. As a readout of action, cyclopamine inhibits hedgehog-dependent expression of Pax7 with an IC50 value of 24 nM. Although teratogenic during development, cyclopamine has potential applications in the treatment of cancer.

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

Cyclopamine, is used as a hedgehog [Hh] signaling pathway and Smo inhibitor. It depletes stem-like cancer cells in glioblastoma and blocks tumor engraftment. Can also be used to induce differentiation of human embryonic stem cells (hESCs) into hormone-expressing endocrine cells.

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

Definition

ChEBI: Cyclopamine is a member of piperidines. It has a role as a glioma-associated oncogene inhibitor.

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).

storage

+4°C

References

1) Watkins et al. (2003), Hedgehog signalling within airway epithelial progenitors and in small-cell lung cancer; Nature, 422 313

CYCLOPAMINE Preparation Products And Raw materials

Raw materials

Preparation Products

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CYCLOPAMINE Suppliers

Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
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AdooQ Bioscience CHINA
Tel
025-58849295 18951903616;
Fax
025-68650336
Email
info@adooq.cn
Country
China
ProdList
2990
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60
Nanjing Spring & Autumn Biological Engineering Co., Ltd.
Tel
025-84430028 13815430202
Email
sale02@cqherb.com
Country
China
ProdList
281
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59
Shanghai Fuorain BioTech Co., Ltd
Tel
18672534757
Email
xiaoxue.hu@fuorain.cn
Country
China
ProdList
1858
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58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
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55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
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76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
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Jia Xing Isenchem Co.,Ltd
Tel
0573-85285100 18627885956
Fax
0573-85285100
Email
isenchem@163.com
Country
China
ProdList
9513
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Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
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64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
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50
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View Lastest Price from CYCLOPAMINE manufacturers

Chongqing Zhihe Biopharmaceutical Co., Ltd.
Product
CYCLOPAMINE 4449-51-8
Price
US $0.00-0.00/kg
Min. Order
0.10000000149011612kg
Purity
≥98%
Supply Ability
20tons
Release date
2024-01-03
Shanghai Standard Technology Co., Ltd.
Product
Cyclopamine 4449-51-8
Price
US $0.00/mg
Min. Order
20mg
Purity
≥98%(HPLC)
Supply Ability
100 g
Release date
2020-08-13
NanJing Spring & Autumn Biological Engineering CO., LTD.
Product
Cyclopamine 4449-51-8 4449-51-8
Price
US $490.00/g
Min. Order
10mg
Purity
≥98%
Supply Ability
1000.00 KGS
Release date
2019-06-27

4449-51-8, CYCLOPAMINERelated Search:


  • 11-DEOXOJERVINE
  • CyclopaMine, froM VeratruM californiciM
  • CYCLOPAMINE
  • 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)-
  • Cyclopamine 11-Deoxojervine (3b,23b)-17,23-Epoxy-11-deoxoveratraman-3-ol
  • Cyclopamine, >=98%
  • (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
  • 11-DEOXYJERVINE
  • (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
  • Cyclopamine hydrate,11-deoxojervine hydrate
  • CyclopaMine (11-deoxojervine)
  • 17,23β-Epoxyveratraman-3β-ol
  • 17β,23β-Epoxyveratraman-3β-ol
  • (3b,23b)-17,23-Epoxy-11-deoxoveratraman-3-ol
  • 11-deoxo-jervin
  • 17,23-epoxy-,(3-beta,23-beta)-veratraman-3-o
  • alkaloidv
  • (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-
  • CYCLOPAMINE(RG)
  • Cyclopamine, 98%, from Veratrum californicum Durand
  • Cyclopamine 99+%
  • 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
  • (3S,3''R,3''aS,6''S,6aS,9S)-3'',6'',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2''-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol
  • Compound T3525
  • Cyclopamine (ethanol solution)
  • (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
  • (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-3-ol
  • Cyclopamine in methanol
  • 4449-51-8
  • C27H41NO2
  • Inhibitors
  • antibiotic
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Steroids
  • Lipid signaling