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D2926

Sigma-Aldrich

Diphenyleneiodonium chloride

≥98%

Synonyme(s) :

DPI, Dibenziodolium chloride

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About This Item

Formule empirique (notation de Hill):
C12H8ClI
Numéro CAS:
Poids moléculaire :
314.55
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

Essai

≥98%

Forme

powder

Pf

278 °C

Solubilité

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

Température de stockage

room temp

Chaîne SMILES 

[Cl-].[I+]1c2ccccc2-c3ccccc13

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

Clé InChI

FCFZKAVCDNTYID-UHFFFAOYSA-M

Informations sur le gène

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Application

Diphenyleneiodonium chloride has been used as an NOX inhibitor:
  • to study its effects on the reactive oxygen species (ROS) levels and also its inhibitory effects on killing tumor cells by neutrophils isolated from clinical malignant pleural effusion (MPE) samples[1]
  • as a nicotinamide adenine dinucleotide phosphate (NADPH) oxidase inhibitor to confirm the variation in inflammation was secondary to overproduction of reactive oxygen species (ROS) in cells treated with doxorubicin (DOX) + flagellin (FL)[2]
  • as an NADPH oxidase (NOX) inhibitor to study its effects on palmitate (PA)-induced sphere-forming ability of HepG2 (hepatocellular carcinoma) cells[3]

Actions biochimiques/physiologiques

A potent and reversible inhibitor of nitric oxide synthetase from macrophages and endothelial cells. Also inhibits other flavoenzymes such as neutrophil NADPH oxidase.
A potent reversible nitric oxide synthetase inhibitor from macrophages and endothelial cells.
Diphenyleneiodonium (DPI) can affect mitochondrial function. DPI can block neuron degeneration in Parkinson′s disease. It provides neuroprotection following focal cerebral ischemia. DPI can induce a chemo-quiescence phenotype in cancer stem-like cells, effectively inhibiting their proliferation.[4]

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


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Certificats d'analyse (COA)

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DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Questions

1–5 sur 5 questions  
  1. Will the solution stability of Product No. D2926, Diphenyleneiodonium chloride be extended if kept at -80°C?

    1 réponse
    1. The solution stability at -80°C is not determined.

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  2. What is the solution stability of Product No. D2926, Diphenyleneiodonium chloride?

    1 réponse
    1. A stock solution of D2926 in DMSO can be stored at -20°C for up to 3 months.

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  3. Product No. D2926 is an inhibitor of nitric oxide synthase (NOS). Does Sigma-Aldrich offer any other NOS inhibitors?

    1 réponse
    1. We do offer other inhibitors of NOS, such as Product Nos. M7033 (NG-Methyl-L-arginine) and A7009 (Aminoguanidine).

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  4. What is the Department of Transportation shipping information for this product?

    1 réponse
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  5. How should Product No. D2926, Diphenyleneiodonium chloride be dissolved?

    1 réponse
    1. Product D2926 is soluble in DMSO at a concentration of 10 mg/mL, with strong heating. It is also easily soluble at 2.4 mg/mL in DMSO, in 0.1N NaOH (at 0.5 mg/mL), in 0.1N HCl (at 0.2 mg/mL), in ethanol (at 0.2 mg/mL) or in water (0.2 mg/mL). Stock solutions can be prepared at 10 mM in DMSO, according to O'Donnell, V. B., et al., Studies on the Inhibitory Mechanism of Iodonium Compounds with Special Reference to Neutrophil NADPH Oxidase. Biochem. J., 290(pt 1), 41-49 (1993), or at 3 x 10-8 to 3 x 10-6 M in a 5% glucose solution according to Wang, Y. X., et al., Inhibitory Actions of Diphenyleneiodonium on Endothelium-dependent Vasodilatations In Vitro and In Vivo. Br. J.Pharmacol., 110(3), 1232-1238 (1993).

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