DIPHENYLENEIODONIUM

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H8I
Molecular Weight	279.0964
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

[I+]1C2=CC=CC=C2C3=C1C=CC=C3

InChI

InChIKey=QFXKXRXFBRLLPQ-UHFFFAOYSA-N

InChI=1S/C12H8I/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H/q+1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11577997 | https://www.ncbi.nlm.nih.gov/pubmed/28961864 | https://www.ncbi.nlm.nih.gov/pubmed/28682956

Diphenyleneiodonium chloride is an irreversible inhibitor of nitric oxide synthases, iNOS and eNOS, NADPH cytochrome P450 oxidoreductase and inhibits preferentially the plasma membrane NADH oxidase (NOX) activity. Diphenyleneiodonium chloride exhibits potent antimicrobial activity against non-tuberculous mycobacteria and possesses a potentially new mechanism of action. Besides, experiments on diabetic animal models have shown, that diphenyleneiodonium mitigates sciatic nerve damage by attenuating oxidative stress.

Approval Year

Targets

Primary Target	Pharmacology	Potency
NADPH--cytochrome P450 reductase 2 Target ID: P16435 Gene ID: 5447.0 Gene Symbol: POR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8399148	Inhibitor 8297	2.8 mM [Ki]
Nitric oxide synthase (inducible and endothelial) 9 Target ID: CHEMBL2111350 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11577997	Inhibitor 8297
NADPH oxidase 1 6 Target ID: Q9Y5S8 Gene ID: 27035.0 Gene Symbol: NOX1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11970854	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Non-tuberculous mycobacterial infections 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28961864	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Transcriptional activation of the human manganese superoxide dismutase gene mediated by tetradecanoylphorbol acetate.	1999 Dec 24	10601319
DJ-1 is an indicator for endogenous reactive oxygen species elicited by endotoxin.	2001 Dec	11811539
Proteasome inhibitors stimulate activator protein-1 pathway via reactive oxygen species production.	2002 Aug 28	12208513
Arsenic trioxide-induced apoptosis is independent of stress-responsive signaling pathways but sensitive to inhibition of inducible nitric oxide synthase in HepG2 cells.	2003 Apr 30	12754411
Endothelin-1 increases vascular superoxide via endothelin(A)-NADPH oxidase pathway in low-renin hypertension.	2003 Feb 25	12600921
Redox regulation of HIF-1alpha levels and HO-1 expression in renal medullary interstitial cells.	2003 Jun	12595275
Lipopolysaccharide induces matrix metalloproteinase-9 expression via a mitochondrial reactive oxygen species-p38 kinase-activator protein-1 pathway in Raw 264.7 cells.	2004 Dec 1	15557194
Arrestin regulates MAPK activation and prevents NADPH oxidase-dependent death of cells expressing CXCR2.	2004 Nov 19	15364949
Doxorubicin activates nuclear factor of activated T-lymphocytes and Fas ligand transcription: role of mitochondrial reactive oxygen species and calcium.	2005 Jul 15	15799720
Reactive oxygen species generation is involved in epidermal growth factor receptor transactivation through the transient oxidization of Src homology 2-containing tyrosine phosphatase in endothelin-1 signaling pathway in rat cardiac fibroblasts.	2006 Apr	16391241
Matrix metalloproteinase-2 and -9 are induced differently by doxorubicin in H9c2 cells: The role of MAP kinases and NAD(P)H oxidase.	2006 Feb 15	16213474
c-Jun N-terminal kinase inhibition and alpha-tocopherol protect midbrain dopaminergic neurons from interferon-gamma/lipopolysaccharide-induced injury without affecting nitric oxide production.	2006 Jan	16307444
Notoginsenoside R1 inhibits TNF-alpha-induced fibronectin production in smooth muscle cells via the ROS/ERK pathway.	2006 May 1	16632126
Methylglyoxal-induced fibronectin gene expression through Ras-mediated NADPH oxidase activation in renal mesangial cells.	2007 Aug	17635749
Crocetin attenuates palmitate-induced insulin insensitivity and disordered tumor necrosis factor-alpha and adiponectin expression in rat adipocytes.	2007 Jul	17471172
Homocysteine and copper interact to promote type 5 phosphodiesterase expression in rabbit cavernosal smooth muscle cells.	2008 Nov	18097500
Activation of ROS/NF-kappaB and Ca2+/CaM kinase II are necessary for VCAM-1 induction in IL-1beta-treated human tracheal smooth muscle cells.	2009 May 15	19281832
NADPH oxidase and lipid raft-associated redox signaling are required for PCB153-induced upregulation of cell adhesion molecules in human brain endothelial cells.	2009 Oct 15	19632255
Role and mechanism of arsenic in regulating angiogenesis.	2011	21687637
Cellular iron depletion weakens induction of heme oxygenase-1 by cadmium.	2011 Jan	20934533
Lipid raft-dependent death receptor 5 (DR5) expression and activation are critical for ursodeoxycholic acid-induced apoptosis in gastric cancer cells.	2011 May	21362627
Insulin increases surface expression of TRPC6 channels in podocytes: role of NADPH oxidases and reactive oxygen species.	2012 Feb 1	22031853
Cadmium induces matrix metalloproteinase-9 expression via ROS-dependent EGFR, NF-кB, and AP-1 pathways in human endothelial cells.	2015 Dec 2	26514923

Patents

Sample Use Guides

In Vivo Use Guide

Diabetic Neuropathy Rat Model: diphenyleneiodonium (DPI) chloride (1 mg/kg) was injected subcutaneously 24 hours and 30 minutes before the sciatic block

Route of Administration: Other

In Vitro Use Guide

Diphenyleneiodonium chloride (DPI) effectively inhibited NO production (IC50=0.03+/-0.004 microM), as evaluated by the method of Griess. Nuclear factor-kappa B (NF-kappaB) activation, as evaluated by electrophoretic mobility shift assay, was inhibited by DPI (1-10 microM) in a dose-dependent manner. IL-1-induced ROS production, as evaluated by measurement of dichlorofluorescein fluorescence, was inhibited by DPI at concentrations that also prevented NF-kappaB activation and iNOS expression.

Name

Type

Language

DIPHENYLENEIODONIUM

Common Name

English

DIBENZIODOLIUM

Systematic Name

English

Code System Code Type Description

PUBCHEM

3101