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Submit ReviewDiphenyleneiodonium chloride
Description: GPR3 agonist; also inhibits NOS and NADPH oxidases
Alternative Names: DPI
Chemical Name: [1,1'-Biphenyl]-2,2'-diyliodonium chloride
Purity: ≥99% (HPLC)
Biological Activity for Diphenyleneiodonium chloride
Diphenyleneiodonium chloride is a GPR3 agonist (EC50 = 1 μM); activates adenylate cyclase through GPR3 but not GPR6 or GPR12. Also induces Ca2+ mobilization and β-arrestin receptor internalization. Binds strongly to flavoproteins; inhibits several enzymes, including NO synthase, NADPH oxidases and NADPH cytochrome P450 oxidoreductase. Also inhibits platelet aggregation.
Technical Data for Diphenyleneiodonium chloride
| M. Wt | 314.55 |
| Formula | C12H8ClI |
| Storage | Desiccate at -20°C |
| Purity | ≥99% (HPLC) |
| CAS Number | 4673-26-1 |
| PubChem ID | 2733504 |
| InChI Key | FCFZKAVCDNTYID-UHFFFAOYSA-M |
| Smiles | [Cl-].c1c2c3ccccc3[i+]c2ccc1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Diphenyleneiodonium chloride
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 3.14 | 10 |
Preparing Stock Solutions for Diphenyleneiodonium chloride
The following data is based on the product molecular weight 314.55. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.1 mM | 31.79 mL | 158.96 mL | 317.91 mL |
| 0.5 mM | 6.36 mL | 31.79 mL | 63.58 mL |
| 1 mM | 3.18 mL | 15.9 mL | 31.79 mL |
| 5 mM | 0.64 mL | 3.18 mL | 6.36 mL |
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Product Datasheets for Diphenyleneiodonium chloride
References for Diphenyleneiodonium chloride
References are publications that support the biological activity of the product.
Stuehr et al (1991) Inhibition of macrophage and endothelial cell nitric oxide synthase by diphenyleneiodonium and its analogs. FASEB J. 5 98 PMID: 1703974
Wang et al (1993) Inhibitory actions of diphenyleneiodonium dependent vasodilations in vitro and in vivo. Br.J.Pharmacol. 110 1232 PMID: 7507779
Yea et al (1990) Purification and some properties of the 45 kDa diphenylene iodonium-binding flavoprotein of neutrophil NADPH oxidase. Biochem.J. 265 95 PMID: 2154184
Tew (1993) Inhibition of cytochrome P450 reductase by the diphenyliodonium cation. Kinetic analysis and covalent modifications. Biochemistry 32 10209 PMID: 8399148
Ye et al (2014) Identification of a novel small-molecule agonist for human G protein-coupled receptor 3. J.Pharmacol.Exp.Ther. 349 437 PMID: 24633425
If you know of a relevant reference for Diphenyleneiodonium chloride, please let us know.
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Keywords: Diphenyleneiodonium chloride, Diphenyleneiodonium chloride supplier, Binds, flavoproteins, inhibits, inhibitors, NOS, Nitric, Oxide, synthase, Signaling, Signalling, NADH, NADPH, reductase, oxidase, GPR3, DPI, Other, Oxidase, Orphan, 7-TM, Receptors, 0504, Tocris Bioscience
5 Citations for Diphenyleneiodonium chloride
Citations are publications that use Tocris products. Selected citations for Diphenyleneiodonium chloride include:
Ruparel et al (2012) Plasticity of cytochrome P450 isozyme expression in rat trigeminal ganglia neurons during inflammation. Cancer Med 153 2031 PMID: 22633978
Gonsalves et al (2014) Angiogenic growth factors augment K-Cl cotransporter expression in erythroid cells via hypoxia-inducible factor-1α. Am J Hematol 89 273 PMID: 24227191
Knight et al (2013) Peptidylarginine deiminase inhibition is immunomodulatory and vasculoprotective in murine lupus. J Clin Invest 123 2981 PMID: 23722903
Leoni et al (2013) Annexin A1, formyl peptide receptor, and NOX1 orchestrate epithelial repair. J Clin Invest 123 443 PMID: 23241962
Kim et al (2019) Role of miRNA-181a-2-3p in cadmium-induced inflammatory responses of human bronchial epithelial cells. J Thorac Dis 11 3055 PMID: 31463135
Do you know of a great paper that uses Diphenyleneiodonium chloride from Tocris? Please let us know.
Reviews for Diphenyleneiodonium chloride
Average Rating: 5 (Based on 1 Review.)
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a GPR3 agonist..
By
Anonymous on 05/02/2018
Assay Type: Ex Vivo
Species: Rat
It is a GPR3 agonist and also inhibits NADPH oxidase.It increases cAMP in cultured astrocytes.