Diphenyleneiodonium chloride

Modify Date: 2024-01-09 16:12:04

Diphenyleneiodonium chloride Structure
Diphenyleneiodonium chloride structure
Common Name Diphenyleneiodonium chloride
CAS Number 4673-26-1 Molecular Weight 314.54900
Density N/A Boiling Point N/A
Molecular Formula C12H8ClI Melting Point 312-322ºC
MSDS Chinese USA Flash Point N/A

 Use of Diphenyleneiodonium chloride


Diphenyleneiodonium chloride is a NADPH oxidase (NOX) inhibitor and also functions as a TRPA1 activator with an EC50 of 1 to 3 μM.

 Names

Name dibenziodolium chloride
Synonym More Synonyms

 Diphenyleneiodonium chloride Biological Activity

Description Diphenyleneiodonium chloride is a NADPH oxidase (NOX) inhibitor and also functions as a TRPA1 activator with an EC50 of 1 to 3 μM.
Related Catalog
Target

NOX[1] EC50: 1 to 3 μM (TRPA1)[1]

In Vitro Diphenyleneiodonium chloride is a NADPH oxidase (NOX) inhibitor and also functions as a TRPA1 activator with an EC50 of 1 to 3 μM. Application of Diphenyleneiodonium chloride to HEK-TRPA1 cells at a concentration ranges of 0.03 to 10 μM effectively induces a Ca2+ response. However, Diphenyleneiodonium chloride fails to evoke a Ca2+ response in control HEK cells, even at a relatively high dose of 10 μM[1]. When Diphenyleneiodonium chloride is included in the co-cultures, lipopolysaccharide (LPS)-induced preOL apoptosis is significantly inhibited. Treatment with Diphenyleneiodonium chloride is found to significantly attenuate the LPS-induced O2- production by 2.0-fold, reducing it to within 27% of the controls[2].
In Vivo Intraplantar injection of 2 mM Diphenyleneiodonium chloride to the hindpaw causes licking or biting behavior[1]. Diphenyleneiodonium chloride treatment immediately or 24 h after lipopolysaccharide (LPS) injection significantly attenuates the LPS-induced loss of O4 positive cells. Treatment with Diphenyleneiodonium chloride either immediately or 24 h after LPS injection significantly ameliorates the LPS-induced disorganization of the white matter nerve fibers. However, treatment with DPI 48 h after LPS injection does not appear to correct the LPS-induced white matter damage. DPI treatment either immediately or 24 h after LPS injection significantly reduces the accumulation of both gp91phox and p67phox in the membrane fraction[2].
Cell Assay Purified microglia and preOLs are co-cultured using a Transwell culture system. Co-cultured cells are divided into three groups: control, lipopolysaccharide (LPS)-activated, and LPS plus Diphenyleneiodonium chloride. Microglia are cultured in Transwells over established preOL layers and exposed to either LPS (100 ng/mL), LPS+Diphenyleneiodonium chloride (10 μM) or untreated. The medium supernatants and cellular protein fractions from the co-cultures are then collected for further analysis after 48 h incubation[2].
Animal Admin The ddy mice (6 to 7 wk of age) are individually placed in transparent cages for 30 min before experiments. An intraplantar injection of 10 μL Diphenyleneiodonium chloride (2 mM, solvent: Kolliphor EL with 20% DMSO) is then injected into the right hindpaw with or without intraperitoneal administration with HC030031 (300 mg/kg at 0.5 h prior to injection of Diphenyleneiodonium chloride; solvent: saline with 0.5% methyl cellulose). The time spent licking or biting the injected paw is recorded for 45 min after injection[1].
References

[1]. Suzuki H, et al. The NADPH oxidase inhibitor diphenyleneiodonium activates the human TRPA1 nociceptor. Am J Physiol Cell Physiol. 2014 Aug 15;307(4):C384-94.

[2]. He YF, et al. Diphenyleneiodonium protects preoligodendrocytes against endotoxin-activated microglial NADPH oxidase-generated peroxynitrite in a neonatal rat model of periventricular leukomalacia. Brain Res. 2013 Jan 25;1492:108-21.

 Chemical & Physical Properties

Melting Point 312-322ºC
Molecular Formula C12H8ClI
Molecular Weight 314.54900
Exact Mass 313.93600
Appearance of Characters Powder | Off-white
Storage condition -20°C

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Risk Phrases 36
Safety Phrases 26
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2903999090

 Synthetic Route

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Diphenyleneiodonium chloride Structure

Diphenyleneiodo...

CAS#:4673-26-1

Literature: Journal of the American Chemical Society, , vol. 74, p. 274

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Diphenyleneiodonium chloride Structure

Diphenyleneiodo...

CAS#:4673-26-1

Literature: Journal of Organic Chemistry, , vol. 34, # 2 p. 456 - 457

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Diphenyleneiodonium chloride Structure

Diphenyleneiodo...

CAS#:4673-26-1

Literature: Chemische Berichte, , vol. 88, p. 268

~%

Diphenyleneiodonium chloride Structure

Diphenyleneiodo...

CAS#:4673-26-1

Literature: Chemische Berichte, , vol. 88, p. 268

 Customs

HS Code 2903999090
Summary 2903999090 halogenated derivatives of aromatic hydrocarbons VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

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 Synonyms

Diphenyleneiodonium chloride
DPI Dibenziodolium chloride
MFCD00214165