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Merck

D2926

Diphenyleneiodonium chloride

≥98%, Nitric oxide synthetase inhibitor, powder

Synonym(s):

DPI, Dibenziodolium chloride

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About This Item

Empirical Formula (Hill Notation):
C12H8ClI
CAS Number:
4673-26-1
Molecular Weight:
314.55
UNSPSC Code:
12352200
PubChem Substance ID:
24278032
NACRES:
NA.77
MDL number:
MFCD00214165
Assay:
≥98%
Form:
powder
Quality level:
300

Key Documents

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Product Name

Diphenyleneiodonium chloride, ≥98%

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

assay

≥98%

form

powder

mp

278 °C

solubility

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

storage temp.

room temp

Quality Level

300

Gene Information

human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)
mouse ... Pik3r1(18708)

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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.
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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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

D2926-BULK: + D2926-10MG:4548173990521 + D2926-50MG-PW: + D2926-VAR: + D2926-50MG:4548173990538 + D2926-10MG-PW:

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Certificates of Analysis (COA)

Lot/Batch Number
0000508218
0000508217
0000508217
0000508218
0000383061

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Guei-Sheung Liu et al.
Journal of tissue engineering and regenerative medicine, 10(3), E167-E176 (2013-07-31)
Adipose-derived stem cells (ASCs) show great potentials in applications such as therapeutic angiogenesis, regenerative medicine and tissue engineering. Pharmacological preconditioning of stem cells to boost the release of cytoprotective factors may represent an effective way to enhance their therapeutic efficacy.
Marcin Zawrotniak et al.
Frontiers in cellular and infection microbiology, 7, 414-414 (2017-10-07)
Neutrophils use different mechanisms to cope with pathogens that invade the host organism. The most intriguing of these responses is a release of neutrophil extracellular traps (NETs) composed of decondensed chromatin and granular proteins with antimicrobial activity. An important potential
Clara Angelina et al.
Scientific reports, 7(1), 16867-16867 (2017-12-06)
Relapse-prone, poor prognosis neuroblastoma is frequently characterized by deletion of chr1p36 where tumor suppressor gene KIF1Bβ resides. Interestingly, many 1p36-positive patients failed to express KIF1Bβ protein. Since altered cellular redox status has been reported to be involved in cell death
Ching-Hou Ma et al.
Redox biology, 14, 72-81 (2017-09-05)
Osteoarthritis (OA) is a degenerative joint disease affecting a large population of people. Although the elevated expression of PKR (double stranded RNA-dependent protein kinase) and MMP-13 (collagenase-3) have been indicated to play pivotal roles in the pathogenesis of OA, the
Mito Kanatsu-Shinohara et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(33), 16404-16409 (2019-07-31)
Because spermatogonial stem cells (SSCs) are immortal by serial transplantation, SSC aging in intact testes is considered to be caused by a deteriorated microenvironment. Here, we report a cell-intrinsic mode of SSC aging by glycolysis activation. Using cultured SSCs, we
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