11-DEOXOJERVINE
Cyclopamine
CAS: 4449-51-8
Molecular Formula: C27H41NO2
11-DEOXOJERVINE - Names and Identifiers
| Name | Cyclopamine |
| Synonyms | Cyclopamine CYCLOPAMINE 11-DEOXYJERVINE 11-DEOXOJERVINE CyclopaMine, froM VeratruM californiciM 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 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)- |
| CAS | 4449-51-8 |
11-DEOXOJERVINE - Physico-chemical Properties
| Molecular Formula | C27H41NO2 |
| Molar Mass | 411.62 |
| Density | 1.0274 (rough estimate) |
| Melting Point | 236-238°C |
| Boling Point | 531.29°C (rough estimate) |
| Specific Rotation(α) | (H2O)-17.4；(c, 1 in MeOH/CHCl3 2:1)-48 |
| Solubility | Soluble in DMSO, insoluble in water |
| Appearance | Powder |
| Color | White |
| pKa | 15.05±0.70(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Stability | Store in Freezer at - 20°C |
| Refractive Index | 1.6400 (estimate) |
| MDL | MFCD09878269 |
| In vitro study | Cyclopamine inhibits Hedgehog signaling pathway with an IC50 of 46 nM, and acts on CHO-K1 cells in [3H]Hh-Ag binding experiments to inhibit the activity of human Smo receptors with an IC50 of 280 nM. Cyclopamine acts on the intestinal tumor cells expressing Patched (PTCH) mRNA, significantly inhibiting the activity of Hedgehog pathway in a dose-dependent manner, and inhibiting the growth of tumor cells at a concentration of 3 μm, inhibition reached 75-95%, but there was no effect on colon cancer cells that did not express PTCH mRNA, indicating that Cyclopamine specifically acts on the Hedgehog pathway and is not toxic. Through direct interaction with Smo to inhibit Hedgehog signal, Cyclopamine (10 μm) inhibited the proliferation of 05.04 of SMOhigh Cyclopamine-reactive cell lines L3.6sl and Panc by 75-80%, and the apoptosis rate increased by 2.5 to 3.5 times, but did not affect the BxPC3-SMOlow cell lines. Cyclopamine treatment of the E3LZ10.7 cell line significantly reduced Snail mRNA and provided E-cadherin transcription. Cyclopamine treatment of Hedgehog-dependent L3.6pl cells significantly inhibited infiltrating cells and reduced metastatic cells by more than 500 times, but had no effect on the Panc-1 of Hedgehog-independent cell lines. |
| In vivo study | Cyclopamine treated mice at a dose of 50 mg/kg daily for 22 days eliminated HUCCT1 xenografts without significant side effects. Cyclopamine treated Panc 05.04 And L3.6sl-driven tumors at a dose of 1.2 mg for 7 days, the former induced significant tumor cell apoptosis, the latter reduced tumor mass by 50-60%, but it has no effect on BxPC3-SMOlow tumors. Cyclopamine alone treated E3LZ10.7 and L3.6pl xenografts, significantly inhibited tumor metastasis, and combined with Gemcitabine treatment, completely abolished metastasis. |
11-DEOXOJERVINE - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | GY0750000 |
| HS Code | 29349990 |
11-DEOXOJERVINE - Reference Information
| Use | antibacterial properties of cyclopamine. Cyclopamine shows teratogenic properties and has been shown to reverse the effects of smoothing and oncogenic mutations in patches. Potent Hedgehog inhibitor. Solubility: when heated to about 70 degrees (about 12 mmol Sol), dissolve 1mg cyclopamine in 0.2ml DMSO for content determination/identification/pharmacological experiments, etc |
| cyclopamine | , it is a kind of steroidal alkaloid isolated from the genus Veratrum, which is mainly found in the plants of Liliaceae, Veratrum calicium and Indian deer. And the four plants of Veratrum and Fritillaria pallifloa Schrenk can bind to the Smoothened(Smo) protein in the Hedgehog signaling pathway, thereby inhibiting the activity of the protein.|
| Application | studies since the Nineties have shown that cyclopamine is an inhibitor of hedgehog signaling pathway, it has been confirmed in Drosophila melanogaster that the mutation of hedgehog signaling pathway is associated with the pathogenesis of various tumors. Recent studies have found that cyclopamine has anti-tumor effect in adult, and in pancreatic cancer, cholangiocarcinoma, ovarian cancer, liver cancer and other in vivo or in vitro experiments have been confirmed, but its research in gastric cancer cells, the domestic has not been reported. At present cyclopamine as a potential anti-tumor drug in the world set off a research boom. |
| biological activity | Cyclopamine (11-deoxojevine) is a specific Hedgehog (Hh) signaling pathway antagonist, acting on Smoothened (Smo), The IC50 was 46 nM in TM3Hh12 cells. |
| Target | Value |
| Smoothened (TM3Hh12 cells) | 46 nM |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:48:19
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