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D2926

Sigma-Aldrich

Diphenyleneiodonium chloride

≥98%

Synonym(s):

DPI, Dibenziodolium chloride

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About This Item

Empirical Formula (Hill Notation):
C12H8ClI
CAS Number:
Molecular Weight:
314.55
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98%

form

powder

mp

278 °C

solubility

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

storage temp.

room temp

SMILES string

[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

InChI key

FCFZKAVCDNTYID-UHFFFAOYSA-M

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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
  • 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)
  • as an NADPH oxidase (NOX) inhibitor to study its effects on palmitate (PA)-induced sphere-forming ability of HepG2 (hepatocellular carcinoma) cells

Biochem/physiol Actions

A potent and reversible inhibitor of nitric oxide synthetase from macrophages and endothelial cells. Also inhibits other flavoenzymes such as neutrophil NADPH oxidase.
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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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