Voacangine
Based on 1 Customer Validation
Voacangine is an antagonist for TRPV1 and TRPM8 but as an agonist for TRPA1 (EC50=8 μM). Voacangine competitively blockes capsaicin binding to TRPV1 (IC50=50 μM). Voacangine competitively inhibits the binding of menthol to TRPM8 (IC50=9 μM) and it shows noncompetitive inhibition against icilin (IC50=7 μM). Voacangine selectively abrogates chemical agonist-induced TRPM8 activation and did not affect cold-induced activation. Voacangine is an alkaloid isolated from the root bark of Voacanga africana.
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- Pureza: 98.78%
- No. CAS: 510-22-5
- Fòrmula: C22H28N2O3
- Peso molecular:368.47
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Almacenamiento:
4°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
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Actividad biológica
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Chemical Information
- Pureza y Documentación
- Referencias
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Help & FAQs
Actividad biológica
EC50: 8 μM (TRPA1)[1].
IC50: 9 μM (TRPM8)[1].
IC50: 50 μM (TRPV1)[1].
IC50: 7 μM (icilin)[1]
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| DLD-1 | IC50 |
>40 μM
Compound: 1
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Cytotoxicity against Wnt-dependent human DLD1 cells assessed as cell viability after 24 hrs by fluorescence assay
Cytotoxicity against Wnt-dependent human DLD1 cells assessed as cell viability after 24 hrs by fluorescence assay
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[PMID: 26231157] |
| HCT-116 | IC50 |
>40 μM
Compound: 1
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Cytotoxicity against Wnt-dependent human HCT116 cells assessed as cell viability after 24 hrs by fluorescence assay
Cytotoxicity against Wnt-dependent human HCT116 cells assessed as cell viability after 24 hrs by fluorescence assay
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[PMID: 26231157] |
| HEK293 | IC50 |
>40 μM
Compound: 1
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Cytotoxicity against HEK293 cells assessed as cell viability after 24 hrs by fluorescence assay
Cytotoxicity against HEK293 cells assessed as cell viability after 24 hrs by fluorescence assay
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[PMID: 26231157] |
| HEK-293T | EC50 |
8 μM
Compound: 1
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Agonist activity at TRPA1 isolated from human W138 cells expressed in HEK293T cells assessed as intracellular Ca2+ influx by Fluo-4 AM staining-based fluorescence analysis
Agonist activity at TRPA1 isolated from human W138 cells expressed in HEK293T cells assessed as intracellular Ca2+ influx by Fluo-4 AM staining-based fluorescence analysis
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[PMID: 24484240] |
| HEK-293T | IC50 |
>40 μM
Compound: 1
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Cytotoxicity against HEK293T cells assessed as cell viability after 24 hrs by fluorescence assay
Cytotoxicity against HEK293T cells assessed as cell viability after 24 hrs by fluorescence assay
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[PMID: 26231157] |
| HEK-293T | IC50 |
24 μM
Compound: 1
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Antagonist activity at human brain TRPV1 expressed in HEK293T cells assessed as inhibition of heat-induced intracellular Ca2+ influx measured for 42 mins by fluorescence-based assay
Antagonist activity at human brain TRPV1 expressed in HEK293T cells assessed as inhibition of heat-induced intracellular Ca2+ influx measured for 42 mins by fluorescence-based assay
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[PMID: 24484240] |
| HEK-293T | IC50 |
50 μM
Compound: 1
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Antagonist activity at human brain TRPV1 expressed in HEK293T cells assessed as inhibition of CAP-induced intracellular Ca2+ influx by fluorescence-based assay
Antagonist activity at human brain TRPV1 expressed in HEK293T cells assessed as inhibition of CAP-induced intracellular Ca2+ influx by fluorescence-based assay
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[PMID: 24484240] |
| HeLa | EC50 |
>40 μM
Compound: 23
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Inhibition of lysosomal acidification in human HeLa cells incubated for 3 hrs by LysoTracker Red DND-99 staining based array scan method
Inhibition of lysosomal acidification in human HeLa cells incubated for 3 hrs by LysoTracker Red DND-99 staining based array scan method
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[PMID: 32356659] |
| RKO | IC50 |
>40 μM
Compound: 1
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Cytotoxicity against Wnt-independent human RKO cells assessed as cell viability after 24 hrs by fluorescence assay
Cytotoxicity against Wnt-independent human RKO cells assessed as cell viability after 24 hrs by fluorescence assay
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[PMID: 26231157] |
| SW480 | IC50 |
>40 μM
Compound: 1
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Cytotoxicity against Wnt-dependent human SW480 cells assessed as cell viability after 24 hrs by fluorescence assay
Cytotoxicity against Wnt-dependent human SW480 cells assessed as cell viability after 24 hrs by fluorescence assay
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[PMID: 26231157] |
Voacangine (100 μM; HEK cells) triggeres Ca2+ influx on TRPA1-expressing cells but not on the other TRPs. Voacangine not only suppresses capsaicin (CAP)-induced TRPV1 activation but also suppressed menthol- and icilin-induced TRPM8 activation. Voacangine attenuates CAP-induced TRPV1 activation. Voacangine shows a dose-dependent suppression of response by CAP. Voacangine competitively inhibits CAP on TRPV1. Voacangine is a competitive antagonist and that Voacangine and CAP act at the same recognition site on hTRPV1. Voacangine is an antagonist for TRPV1 and TRPM8 but an agonist for TRPA1. Voacangine selectively blocks CAP- and heat-induced activation of TRPV1. Voacangine is the first naturally occurring TRPM8 antagonist that competes with Menthol. Voacangine selectively blocks chemical agonist induced activation of TRPM8. Voacangine acts as an agonist for TRPA1[1]. Voacangine inhibits the proliferation of HUVECs at an IC50 of 18 μM with no cytotoxic effects. Voacangine decreases the expression levels of hypoxia inducible factor-1α and its target gene, VEGF, in a dose-dependent manner[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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No. CAS 510-22-5
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Appearance Solid
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Peso molecular 368.47
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Fòrmula C22H28N2O3
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Color White to off-white
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SMILES
COC([C@]12[C@@]3([H])[N@@](CCC4=C2NC5=CC=C(OC)C=C54)C[C@@](C[C@@H]3CC)([H])C1)=O
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Structure Classification
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Initial Source
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
4°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
Pureza y Documentación
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Ficha de datos (276 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Terada Y, et al. Activation and inhibition of thermosensitive TRP channels by voacangine, an alkaloid present in Voacanga africana, an African tree. J Nat Prod. 2014;77(2):285-297. [Content Brief]
[2]. Kim Y, et al. A natural small molecule voacangine inhibits angiogenesis both in vitro and in vivo. Biochem Biophys Res Commun. 2012;417(1):330-334. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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