Benvitimod (Tapinarof)
Modify Date: 2024-01-02 11:53:10
Benvitimod (Tapinarof) structure
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Common Name | Benvitimod (Tapinarof) | ||
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| CAS Number | 79338-84-4 | Molecular Weight | 254.32400 | |
| Density | 1.158 | Boiling Point | N/A | |
| Molecular Formula | C17H18O2 | Melting Point | N/A | |
| MSDS | N/A | Flash Point | N/A | |
Use of Benvitimod (Tapinarof)Tapinarof is a natural aryl hydrocarbon receptor (AhR) agonist with an EC50 of 13 nM. |
| Name | 5-(2-phenylethenyl)-2-propan-2-ylbenzene-1,3-diol |
|---|---|
| Synonym | More Synonyms |
| Description | Tapinarof is a natural aryl hydrocarbon receptor (AhR) agonist with an EC50 of 13 nM. |
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| Related Catalog | |
| Target |
EC50: 13 nM (AhR)[1] |
| In Vitro | Tapinarof activates the AhR pathway through direct binding. Tapinarof dose-dependently induces nuclear translocation of AhR in immortalized keratinocytes (HaCaT) (EC50=0.16 nM)[1]. |
| In Vivo | Tapinarof acts through AhR to reduce inflammation in IMQ-treated mice. AhR-sufficient mice on a C57Bl/6 background exhibit a reduced clinical score after treatment with Tapinarof or 6-formylindolo(3,2-b)carbazole (FICZ). In contrast, AhR KO mice do not respond to the anti-inflammatory effects of Tapinarof. FICZ is used as a comparator in these studies and yields similar results, with dramatically reduced inflammatory responses in wild-type, but not AhR KO mice[1]. |
| Cell Assay | HaCaT cells (10,000 cells/well) are cultured in 96-well Greiner μCLEAR plates in 100 μL DMEM with HEPES, Glutamax and 10% fetal bovine serum to confluence. Media is replaced with 100 μL media containing 0.2% heat-inactivated, charcoal-stripped fetal bovine serum and incubated overnight. Titrating concentrations of Tapinarof (10-8 μM ,10-6 μM, 10-4 μM, 0.01 μM, and 1 μM) are added for 30 minutes followed by washing and fixing in ice-cold methanol:acetone (50:50). Samples are blocked with 3% BSA for 1 hour, and then washed again in phosphate buffered saline with 0.1% Tween-20. Next, cells are stained with 50 μL of 1:50 dilution anti-AhR antibody in 3% BSA, followed by 50 μL secondary antibody (1:500 dilution chicken anti-rabbit AlexaFluor488 and 1:2,000 dilution Hoechst 33342) in 3% BSA/phosphate buffered saline. Images are acquired on InCell 2000 and/or Opera. Image analysis is performed using InCell Analyzer Workstation and/or Columbus[1]. |
| Animal Admin | Mice[1] Female BALB/c mice (BALB/cByJRj) are used. Studies are performed using 100 µL of Tapinarof (1%) or FICZ (0.01%, at the limit of solubility) in 60% ethanol: 40% water[1]. |
| References |
| Density | 1.158 |
|---|---|
| Molecular Formula | C17H18O2 |
| Molecular Weight | 254.32400 |
| Exact Mass | 254.13100 |
| PSA | 40.46000 |
| LogP | 4.39160 |
| Storage condition | 2-8℃ |
| 3,5-Dihydroxy-4-isopropyl-trans-stilbene |
| (E)-2-(1-Methylethyl)-5-(2-phenylethenyl)-1,3-benzenediol |
| 3,5-Dihydroxy-4-isopropylstilbene |