Diphenyleneiodonium chloride

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Cat.No. 0504 - Diphenyleneiodonium chloride | C12H8ClI | CAS No. 4673-26-1
Description: GPR3 agonist; also inhibits NOS and NADPH oxidases
Alternative Names: DPI
Chemical Name: [1,1'-Biphenyl]-2,2'-diyliodonium chloride
Purity: ≥99% (HPLC)
Datasheet
Citations (4)
Literature

Biological Activity

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

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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 3.14 10

Preparing Stock Solutions

The following data is based on the product molecular weight 314.55. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.18 mL 15.9 mL 31.79 mL
5 mM 0.64 mL 3.18 mL 6.36 mL
10 mM 0.32 mL 1.59 mL 3.18 mL
50 mM 0.06 mL 0.32 mL 0.64 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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, supplier, Binds, flavoproteins, inhibits, inhibitors, NOS, Nitric, Oxide, synthase, Signaling, Signalling, NADH, NADPH, reductase, oxidase, GPR3, DPI, Orphan, 7-TM, Receptors, Tocris Bioscience

4 Citations for Diphenyleneiodonium chloride

Citations are publications that use Tocris products. Selected citations for Diphenyleneiodonium chloride include:

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

Ruparel et al (2012) Plasticity of cytochrome P450 isozyme expression in rat trigeminal ganglia neurons during inflammation. Cancer Med 153 2031 PMID: 22633978


Do you know of a great paper that uses Diphenyleneiodonium chloride from Tocris? If so please let us know.

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Pathways for Diphenyleneiodonium chloride

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