1. Immunology/Inflammation
  2. Aryl Hydrocarbon Receptor

Tapinarof (Synonyms: WBI 1001; Benvitimod; GSK2894512)

Cat. No.: HY-109044 Purity: 99.74%
Handling Instructions

Tapinarof is a natural aryl hydrocarbon receptor (AhR) agonist with an EC50 of 13 nM.

For research use only. We do not sell to patients.

Tapinarof Chemical Structure

Tapinarof Chemical Structure

CAS No. : 79338-84-4

Size Price Stock Quantity
10 mM * 1 mL in DMSO USD 242 In-stock
Estimated Time of Arrival: December 31
5 mg USD 220 In-stock
Estimated Time of Arrival: December 31
10 mg USD 350 In-stock
Estimated Time of Arrival: December 31
25 mg USD 700 In-stock
Estimated Time of Arrival: December 31
50 mg USD 1100 In-stock
Estimated Time of Arrival: December 31
100 mg USD 1600 In-stock
Estimated Time of Arrival: December 31
200 mg   Get quote  
500 mg   Get quote  

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  • Biological Activity

  • Protocol

  • Technical Information

  • Purity & Documentation

  • References

Description

Tapinarof is a natural aryl hydrocarbon receptor (AhR) agonist with an EC50 of 13 nM.

IC50 & 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].

Clinical Trial
Solvent & Solubility
In Vitro: 

DMSO : ≥ 150 mg/mL (589.81 mM)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.9321 mL 19.6603 mL 39.3205 mL
5 mM 0.7864 mL 3.9321 mL 7.8641 mL
10 mM 0.3932 mL 1.9660 mL 3.9321 mL
*Please refer to the solubility information to select the appropriate solvent.
In Vivo:
  • 1.

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in saline)

    Solubility: ≥ 2.5 mg/mL (9.83 mM); Clear solution

  • 2.

    Add each solvent one by one:  10% DMSO    90% corn oil

    Solubility: ≥ 2.5 mg/mL (9.83 mM); Clear solution

  • 3.

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% saline

    Solubility: ≥ 2.5 mg/mL (9.83 mM); Clear solution

References
Cell Assay
[1]

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].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Administration
[1]

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].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

References
Molecular Weight

254.32

Formula

C₁₇H₁₈O₂

CAS No.

79338-84-4

SMILES

OC1=C(C(C)C)C(O)=CC(/C=C/C2=CC=CC=C2)=C1

Storage
Powder -20°C 3 years
  4°C 2 years
In solvent -80°C 6 months
  -20°C 1 month
Shipping

Room temperature in continental US; may vary elsewhere

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Product Name:
Tapinarof
Cat. No.:
HY-109044
Quantity:

Tapinarof

Cat. No.: HY-109044