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D2926

Sigma-Aldrich

Diphenyleneiodonium chloride

≥98%

Synonym(s):
DPI, Dibenziodolium chloride
Empirical Formula (Hill Notation):
C12H8ClI
CAS Number:
Molecular Weight:
314.55
MDL number:
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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This Item
54801443088153591
assay

≥98%

assay

≥98%

assay

≥98.0% (AT)

assay

98%

form

powder

form

-

form

-

form

powder

solubility

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

solubility

-

solubility

-

solubility

organic solvents: soluble

storage temp.

room temp

storage temp.

-

storage temp.

-

storage temp.

-

Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

200

mp

278 °C

mp

140-144 °C (lit.)

mp

233-235 °C (subl.) (lit.)

mp

-

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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