Tapinarof

Catalog No.S9700 Batch:S970001

Technical Data

Formula

C₁₇H₁₈O₂

Molecular Weight

254.32

CAS No.

79338-84-4

Solubility (25°C)*

In vitro

DMSO

51 mg/mL (200.53 mM)

Ethanol

51 mg/mL (200.53 mM)

Water

Insoluble

In vivo (Add solvents to the product individually and in order)

Clear solution	5% DMSO 1 95% Corn oil	0.85mg/ml	Taking the 1 mL working solution as an example, add 50 μL of 17 mg/ml clear DMSO stock solution to 950 μL of corn oil and mix evenly. The mixed solution should be used immediately for optimal results.
Clear solution	5%DMSO 1 40%PEG300 2 5%Tween80 3 50%ddH2O	2.5mg/ml	Taking the 1 mL working solution as an example, add 50 μL of 50 mg/ml clarified DMSO stock solution to 400 μL of PEG300, mix evenly to clarify it; add 50 μL of Tween80 to the above system, mix evenly to clarify; then continue to add 500 μL of ddH2O to adjust the volume to 1 mL. The mixed solution should be used immediately for optimal results.

* <1 mg/ml means slightly soluble or insoluble.
* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.
* Room temperature shipping (Stability testing shows this product can be shipped without any cooling measures.)

Preparing Stock Solutions

Biological Activity

Description

Tapinarof (GSK2894512, Benvitimod, WBI 1001, DHPS, DMVT 505) is a natural agonist of aryl hydrocarbon receptor (AhR) and induces nuclear translocation of AhR in immortalized keratinocytes (HaCaT) with EC50 of 0.16 nM. Tapinarof induces cellular apoptosis in CD4+ T cells in a dosedependent manner with IC50 of 5.2 μM.

Targets

AhR ^[1] (in immortalized keratinocytes)	apoptosis ^[1] (in CD4+ T cells)
0.16 nM(EC50)	5.2 μM

In vitro

Tapinarof binds and activates AhR in multiple cell types, including cells of the target tissue –human skin. In addition, tapinarof moderates proinflammatory cytokine expression in stimulated peripheral blood CD4+ T cells and ex vivo human skin, and impacts barrier gene expression in primary human keratinocytes; both of these processes are likely to be downstream of AhR activation based on current evidence.^[1]

In vivo

The anti-inflammatory properties of tapinarof derive from AhR agonism is conclusively demonstrated using the mouse model of imiquimod-induced psoriasiform skin lesions. Topical treatment of AhR-sufficient mice with tapinarof leads to compound-driven reductions in erythema, epidermal thickening and tissue cytokine levels. In contrast, tapinarof has no impact on imiquimod-induced skin inflammation in AhR-deficient mice.^[1]

Protocol (from reference)

Cell Assay:^{^[1]}	Cell lines HaCaT cells Concentrations 0.01 pM - 1 μM Incubation Time 30 min Method HaCaT cells (10,000 cells/well) are cultured in 96-well plates in 100 μL DMEM with HEPES, Glutamax and 10% FBS to confluence. Media is replaced with 100 μl media containing 0.2% heat-inactivated, charcoal-stripped FBS and incubated overnight. Titrating concentrations of tapinarof 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, then washed again in PBS with 0.1% Tween-20. Next, cells are stained with 50μL of 1:50 dilution anti-AhR antibody in 3% BSA, followed by 50 μl secondary antibody in 3% BSA/PBS.

Cell Assay:^{^[1]}

Cell lines
HaCaT cells
Concentrations
0.01 pM - 1 μM
Incubation Time
30 min
Method
HaCaT cells (10,000 cells/well) are cultured in 96-well plates in 100 μL DMEM with HEPES, Glutamax and 10% FBS to confluence. Media is replaced with 100 μl media containing 0.2% heat-inactivated, charcoal-stripped FBS and incubated overnight. Titrating concentrations of tapinarof 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, then washed again in PBS with 0.1% Tween-20. Next, cells are stained with 50μL of 1:50 dilution anti-AhR antibody in 3% BSA, followed by 50 μl secondary antibody in 3% BSA/PBS.

References

[1] Susan H Smith, et al. J Invest Dermatol. 2017 Oct;137(10):2110-2119.

Selleck's Tapinarof has been cited by 3 publications

Ruthenium drug BOLD-100 regulates BRAFMT colorectal cancer cell apoptosis through AhR/ROS/ATR signaling axis modulation [ Mol Cancer Res, 2024, 10.1158/1541-7786.MCR-24-0151]	PubMed: 39083088
The Highly Potent AhR Agonist Picoberin Modulates Hh-Dependent Osteoblast Differentiation [ J Med Chem, 2022, 2]	PubMed: 36459434
A whole genome CRISPR screen identifies AHR loss as a mechanism of PARP7 inhibitor resistance [ Mol Cancer Ther, 2022, molcanther.0841.2021]	PubMed: 35439318

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SHIPPING AND STORAGE
Selleck products are transported at room temperature. If you receive the product at room temperature, please rest assured, the Selleck Quality Inspection Department has conducted experiments to verify that the normal temperature placement of one month will not affect the biological activity of powder products. After collecting, please store the product according to the requirements described in the datasheet. Most Selleck products are stable under the recommended conditions.

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