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

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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:

Glycitin MONOCROTALINE GANT61 MK-2206 2HCl Vismodegib (GDC-0449) Dasatinib Purmorphamine Ruxolitinib CYCLOPAMINE DESPIRO-CYCLOPAMINE BODIPY CYCLOPAMINE N-(2-AMINOETHYL) CYCLOPAMINE CYCLOPAMINE-KAAD,KAAD-CYCLOPAMINE,3-KETO-N-(AMINOETHYL-AMINOCAPROYL-DIHYDROCINNAMOYL)CYCLOPAMINE 3-HYDROXY-N-AMINOETHYL-N'-AMINOCAPROYLDIHYDROCINNAMOYL CYCLOPAMINE CY-3-CYCLOPAMINE, POTASSIUM SALT,CYANINE-3 CYCLOPAMINE, POTASSIUM SALT FLUORESCEINYL CYCLOPAMINE 3-KETO-N-AMINOETHYL-N'-AMINOCAPROYLDIHYDROCINNAMOYL CYCLOPAMINE Cyclopamine hedgehog

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