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300260

Sigma-Aldrich

Diphenyleneiodonium Chloride

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

Synonym(s):

Diphenyleneiodonium Chloride, DPI

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$116.00

About This Item

Empirical Formula (Hill Notation):
C12H8ClI
CAS Number:
4673-26-1
Molecular Weight:
314.55
MDL number:
MFCD00214165
UNSPSC Code:
12352200
NACRES:
NA.77

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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

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

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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

NG,NG′-Dimethyl-L-arginine, Dihydrochloride Cell permeable. Endogenous inhibitor of nitric oxide synthesis in vitro and in vivo. Does not exhibit any significant inhibitory effect on NOS activity.

311204

NG,NG′-Dimethyl-L-arginine, Dihydrochloride

L-N⁵-(1-Iminoethyl)ornithine, Dihydrochloride A cell-permeable, more potent inhibitor of endothelial nitric oxide synthase compared to other arginine analogs such as L-NAME and L-NMMA.

400600

L-N⁵-(1-Iminoethyl)ornithine, Dihydrochloride

form

crystalline solid

form

powder

form

solid

form

solid

assay

≥97% (HPLC)

assay

≥98%

assay

≥97% (HPLC)

assay

≥98% (TLC)

Quality Level

100

Quality Level

300

Quality Level

100

Quality Level

100

manufacturer/tradename

Calbiochem®

manufacturer/tradename

-

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

storage temp.

−20°C

storage temp.

room temp

storage temp.

2-8°C

storage temp.

−20°C

solubility

DMSO: 5 mg/mL

solubility

DMSO: 9.80-10.20 mg/mL, clear, colorless to faintly yellow

solubility

water: 50 mg/mL

solubility

water: 1 mg/mL

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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