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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:
4673-26-1
Molecular Weight:
314.55
MDL number:
MFCD00214165
UNSPSC Code:
12352200
PubChem Substance ID:
24278032
NACRES:
NA.77

Quality Level

300

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

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.
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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Certificates of Analysis (COA)

Lot/Batch Number
0000383061
0000383062
0000370620
0000350685
0000350685

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

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

    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. 

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

    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).

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

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

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

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

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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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.
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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
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
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