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300260

Sigma-Aldrich

Diphenyleneiodonium Chloride

A cell-permeable, irreversible inhibitor of endothelial nitric oxide synthase (eNOS).

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Synonym(s):
Diphenyleneiodonium Chloride, DPI
Empirical Formula (Hill Notation):
C12H8ClI
CAS Number:
Molecular Weight:
314.55
MDL number:

Quality Level

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

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This Item
D2926311204400600
Diphenyleneiodonium Chloride A cell-permeable, irreversible inhibitor of endothelial nitric oxide synthase (eNOS).

300260

Diphenyleneiodonium Chloride

Diphenyleneiodonium chloride ≥98%

D2926

Diphenyleneiodonium chloride

assay

≥97% (HPLC)

assay

≥98%

assay

≥97% (HPLC)

assay

≥98% (TLC)

manufacturer/tradename

Calbiochem®

manufacturer/tradename

-

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

Quality Level

100

Quality Level

300

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

room temp

storage temp.

2-8°C

storage temp.

−20°C

storage condition

OK to freeze, protect from light

storage condition

-

storage condition

OK to freeze, desiccated (hygroscopic)

storage condition

OK to freeze, desiccated (hygroscopic)

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Omar Rafael Alemán et al.
Frontiers in immunology, 12, 657393-657393 (2021-06-01)
Human neutrophils express two unique antibody receptors for IgG, the FcγRIIa and the FcγRIIIb. FcγRIIa contains an immunoreceptor tyrosine-based activation motif (ITAM) sequence within its cytoplasmic tail, which is important for initiating signaling. In contrast, FcγRIIIb is a glycosylphosphatidylinositol (GPI)-linked

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