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Diphenyleneiodonium chloride

Names

[ CAS No. ]:
4673-26-1

[ Name ]:
Diphenyleneiodonium chloride

[Synonym ]:
Diphenyleneiodonium chloride
DPI Dibenziodolium chloride
MFCD00214165

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]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel
Research Areas >> Inflammation/Immunology
Research Areas >> Neurological Disease

[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.


[Related Small Molecules]

capsaicin | Capsazepine | EIPA | HC-030031 | SKF-96365 | HC 067047 | AMG 9810 | GSK-1016790A | SAR7334 | PF-4840154 | RN-1734 | AMG-517 | SB-366791 | IcilinAG-3-5 | ML204

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

MSDS

Click to get detail MSDS

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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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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