CYCLOPAMINE
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- CAS-Nr.
- 4449-51-8
- Englisch Name:
- CYCLOPAMINE
- Synonyma:
- alkaloidv;CYCLOPAMINE;Compound T3525;11-DEOXOJERVINE;11-DEOXYJERVINE;11-deoxo-jervin;CYCLOPAMINE(RG);Cyclopamine 99+%;Cyclopamine, >=98%;Cyclopamine 4449-51-8
- CBNumber:
- CB7677669
- Summenformel:
- C27H41NO2
- Molgewicht:
- 411.62
- MOL-Datei:
- 4449-51-8.mol
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CYCLOPAMINE Eigenschaften
- Schmelzpunkt:
- 236-238°C
- Siedepunkt:
- 531.29°C (rough estimate)
- Dichte
- 1.0274 (rough estimate)
- Brechungsindex
- 1.6400 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- Löslichkeit
- DMSO: soluble
- Aggregatzustand
- solid
- pka
- 15.05±0.70(Predicted)
- Farbe
- White
- Stabilität:
- Store in Freezer at - 20°C
CYCLOPAMINE Chemische Eigenschaften,Einsatz,Produktion Methoden
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
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 IC
50 value of 24 nM. Although teratogenic during development, cyclopamine has potential applications in the treatment of cancer.
Chemische Eigenschaften
White Crystalline Solid
Verwenden
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
Biologische Aktivität
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 Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
CYCLOPAMINE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.
Global( 235)Lieferanten
- 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
- 4449-51-8
- C27H41NO2
- Inhibitors
- antibiotic
- Chiral Reagents
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Steroids
- Lipid signaling
