300260

Diphenyleneiodonium Chloride

≥97% (HPLC), crystalline solid, eNOS inhibitor, Calbiochem^®

• Synonym(s): Diphenyleneiodonium Chloride, DPI
• Empirical Formula (Hill Notation): C₁₂H₈ClI
• CAS Number: 4673-26-1
• Molecular Weight: 314.55
• MDL number: MFCD00214165
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• product name: Diphenyleneiodonium Chloride, A cell-permeable, irreversible inhibitor of endothelial nitric oxide synthase (eNOS).
• Quality Level: 100
• Assay: ≥97% (HPLC)
• form: crystalline solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: off-white
• solubility: DMSO: 5 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• InChI: 1S/C12H8I.ClH/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11;/h1-8H;1H/q+1;/p-1
• InChI key: FCFZKAVCDNTYID-UHFFFAOYSA-M

Description

General description

A cell-permeable, irreversible endothelial nitric oxide synthase inhibitor. Inhibits iNOS in macrophages (IC₅₀ = 5 nM). Shown to inhibit acetylcholine-induced relaxation of preconstricted rat thoracic aortic rings (IC₅₀ = 180 nM). Blocks K⁺ and Ca²⁺ currents in arterial smooth muscle cells. Inhibitor of mitochondrial NADH-ubiquinone oxidoreductase. Inhibits other NADH utilizing flavoproteins, such as NADPH oxidase in human neutrophils and macrophages. Causes pressor and tachycardiac effects via indirect activation of the sympathetic nervous system.

A cell-permeable, irreversible inhibitor of endothelial nitric oxide synthase (eNOS). Shown to inhibit acetylcholine-induced relaxation of preconstricted rat thoracic aortic rings (IC₅₀ = 180 nM). Also inhibits iNOS in macrophages (IC₅₀ = 50 nM). Blocks K⁺ and Ca²⁺ currents in arterial smooth muscle cells. Inhibitor of mitochondrial NADPH-ubiquinone oxido-reductase.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
eNOS

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 180 nM against endothelial nitric oxide synthase (eNOS)

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Preparation Note

Slight warming is required for complete solubility.

Reconstitution

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Wang, Y.X., et al. 1995. Br. J. Pharmacol.114, 194.
Majander, A., et al. 1994. J. Biol. Chem. 269, 21037.
Weir, E.K., et al. 1994. J. Appl. Physiol. 76, 2611.
Wang, Y.X., et al. 1993. Br. J. Pharmacol.110, 1232.
Wang, Y.X., and Pang, C.C. 1993. Br. J. Pharmacol.109, 1186.
Stuehr, D.J., et al. 1991. FASEB J.5, 98.
Handcock, J.T., and Jones, O.T.G. 1987. Biochem. J.242, 103.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable