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300260

Diphenyleneiodonium Chloride

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

Synonym(s):

Diphenyleneiodonium Chloride, DPI

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About This Item

Empirical Formula (Hill Notation):
C12H8ClI
CAS Number:
4673-26-1
Molecular Weight:
314.55
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00214165
Assay:
≥97% (HPLC)
Form:
crystalline solid
Storage condition:
OK to freeze, protect from light
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Product Name

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

Quality Segment

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

SMILES string

[I+]1c2c(cccc2)c3c1cccc3.[Cl-]

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

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)

Preparation Note

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Slight warming is required for complete solubility.

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

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

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