VoacangineCAS# 510-22-5 |
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| Cas No. | 510-22-5 | SDF | Download SDF |
| PubChem ID | 73255 | Appearance | Powder |
| Formula | C22H28N2O3 | M.Wt | 368.5 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| SMILES | CCC1CC2CC3(C1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC | ||
| Standard InChIKey | MMAYTCMMKJYIAM-RUGRQLENSA-N | ||
| Standard InChI | InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14-,20-,22+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Voacangine is a novel transient receptor potential vanilloid type 1 (TRPV1) antagonist. 2. Voacangine shows mod. cytotoxic activity, also some CNS, brachycardial and hypotensive action. 3. Voacangine significantly suppresses in vitro angiogenesis, such as VEGF-induced tube formation and chemoinvasion. 4. Voacangine competitively inhibits the binding of menthol to TRPM8 (IC50, 9 μM), but it shows noncompetitive inhibition against icilin (IC50, 7 μM), it may contribute to the development of a novel class of stimulus-selective TRPM8 blockers. |
| Targets | TRPV | VEGFR |
Voacangine Dilution Calculator
Voacangine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7137 mL | 13.5685 mL | 27.137 mL | 54.2741 mL | 67.8426 mL |
| 5 mM | 0.5427 mL | 2.7137 mL | 5.4274 mL | 10.8548 mL | 13.5685 mL |
| 10 mM | 0.2714 mL | 1.3569 mL | 2.7137 mL | 5.4274 mL | 6.7843 mL |
| 50 mM | 0.0543 mL | 0.2714 mL | 0.5427 mL | 1.0855 mL | 1.3569 mL |
| 100 mM | 0.0271 mL | 0.1357 mL | 0.2714 mL | 0.5427 mL | 0.6784 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Activation and inhibition of thermosensitive TRP channels by voacangine, an alkaloid present in Voacanga africana, an African tree.[Pubmed:24484240]
J Nat Prod. 2014 Feb 28;77(2):285-97.
Voacangine (1) is an alkaloid found in the root bark of Voacanga africana. Our previous work has suggested that 1 is a novel transient receptor potential vanilloid type 1 (TRPV1) antagonist. In this study, the agonist and antagonist activities of 1 were examined against thermosensitive TRP channels. Channel activity was evaluated mainly using TRP channel-expressing HEK cells and calcium imaging. Herein, it was shown that 1 acts as an antagonist for TRPV1 and TRPM8 but as an agonist for TRPA1 (EC50, 8 muM). The compound competitively blocked capsaicin binding to TRPV1 (IC50, 50 muM). Voacangine (1) competitively inhibited the binding of menthol to TRPM8 (IC50, 9 muM), but it showed noncompetitive inhibition against icilin (IC50, 7 muM). Moreover, the compound selectively abrogated chemical agonist-induced TRPM8 activation and did not affect cold-induced activation. Among these effects, the TRPM8 inhibition profile is unique and noteworthy, because to date no studies have reported a menthol competitive inhibitor of TRPM8 derived from a natural source. Furthermore, this is the first report of a stimulus-selective TRPM8 antagonist. Accordingly, 1 may contribute to the development of a novel class of stimulus-selective TRPM8 blockers.
A natural small molecule voacangine inhibits angiogenesis both in vitro and in vivo.[Pubmed:22155252]
Biochem Biophys Res Commun. 2012 Jan 6;417(1):330-4.
Angiogenesis, the formation of new blood vessels from pre-existing ones, plays a critical role in normal and pathological phenotypes, including solid tumor growth and metastasis. Accordingly, the development of new anti-angiogenic agents is considered an efficient strategy for the treatment of cancer and other human diseases linked with angiogenesis. We have identified Voacangine, isolated from Voacanga africana, as a novel anti-angiogenic agent. Voacangine inhibits the proliferation of HUVECs at an IC(50) of 18 muM with no cytotoxic effects. Voacangine significantly suppressed in vitro angiogenesis, such as VEGF-induced tube formation and chemoinvasion. Moreover, the compound inhibits in vivo angiogenesis in the chorioallantoic membrane at non-toxic doses. In addition, Voacangine decreased the expression levels of hypoxia inducible factor-1alpha and its target gene, VEGF, in a dose-dependent manner. Taken together, these results suggest that the naturally occurring compound, Voacangine, is a novel anti-angiogenic compound.
