Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H8I.Cl |
| Molecular Weight | 314.549 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].[I+]1C2=CC=CC=C2C3=C1C=CC=C3
InChI
InChIKey=FCFZKAVCDNTYID-UHFFFAOYSA-M
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
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 | Condition | Potency |
|---|---|---|---|
Target ID: P16435 Gene ID: 5447.0 Gene Symbol: POR Target Organism: Homo sapiens (Human) |
2.8 mM [Ki] | ||
Target ID: CHEMBL2111350 |
|||
Target ID: Q9Y5S8 Gene ID: 27035.0 Gene Symbol: NOX1 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
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| Arrestin regulates MAPK activation and prevents NADPH oxidase-dependent death of cells expressing CXCR2. | 2004 Nov 19 |
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| Comparison of burst of reactive oxygen species and activation of caspase-3 in apoptosis of K562 and HL-60 cells induced by docetaxel. | 2004 Oct 8 |
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| Doxorubicin activates nuclear factor of activated T-lymphocytes and Fas ligand transcription: role of mitochondrial reactive oxygen species and calcium. | 2005 Jul 15 |
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| Hypertonic induction of COX-2 in collecting duct cells by reactive oxygen species of mitochondrial origin. | 2005 Oct 14 |
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| 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 |
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| 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 |
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| Increased RhoA/Rho-kinase signaling mediates spontaneous tone in aorta from angiotensin II-induced hypertensive rats. | 2006 Jul |
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| Elevated concentrations of nonesterified fatty acids increase monocyte expression of CD11b and adhesion to endothelial cells. | 2006 Mar |
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| Notoginsenoside R1 inhibits TNF-alpha-induced fibronectin production in smooth muscle cells via the ROS/ERK pathway. | 2006 May 1 |
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| Crocetin attenuates palmitate-induced insulin insensitivity and disordered tumor necrosis factor-alpha and adiponectin expression in rat adipocytes. | 2007 Jul |
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| Diesel exhaust particles induce matrix metalloprotease-1 in human lung epithelial cells via a NADP(H) oxidase/NOX4 redox-dependent mechanism. | 2007 Jul |
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| Anti-inflammatory effects of the advanced glycation end product inhibitor LR-90 in human monocytes. | 2007 Mar |
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| Paraquat increases cyanide-insensitive respiration in murine lung epithelial cells by activating an NAD(P)H:paraquat oxidoreductase: identification of the enzyme as thioredoxin reductase. | 2007 Mar 16 |
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| Hypoxia stabilizes type 2 deiodinase activity in rat astrocytes. | 2007 Oct |
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| Activation of endothelial cells after exposure to ambient ultrafine particles: the role of NADPH oxidase. | 2009 Apr 15 |
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| Overexpression of HO-1 protects against TNF-alpha-mediated airway inflammation by down-regulation of TNFR1-dependent oxidative stress. | 2009 Aug |
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| Low concentration of arsenic could induce caspase-3 mediated head kidney macrophage apoptosis with JNK-p38 activation in Clarias batrachus. | 2009 Dec 15 |
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| NADPH oxidase and ERK1/2 are involved in cadmium induced-STAT3 activation in HepG2 cells. | 2009 Jun 22 |
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| A benzoxazine derivative induces vascular endothelial cell apoptosis in the presence of fibroblast growth factor-2 by elevating NADPH oxidase activity and reactive oxygen species levels. | 2009 Sep |
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| Cellular mechanisms of IL-17-induced blood-brain barrier disruption. | 2010 Apr |
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| Protection of podocytes from hyperhomocysteinemia-induced injury by deletion of the gp91phox gene. | 2010 Apr 15 |
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| Contribution of reactive oxygen species to migration/invasion of human glioblastoma cells U87 via ERK-dependent COX-2/PGE(2) activation. | 2010 Jan |
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| The role of NOX enzymes in ethanol-induced oxidative stress and apoptosis in mouse embryos. | 2010 Mar 1 |
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| Role and mechanism of arsenic in regulating angiogenesis. | 2011 |
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| Regulation of cyclooxygenase-2 and cytosolic phospholipase A2 gene expression by lipopolysaccharide through the RNA-binding protein HuR: involvement of NADPH oxidase, reactive oxygen species and mitogen-activated protein kinases. | 2011 Aug |
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| Dual function of protein kinase C (PKC) in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced manganese superoxide dismutase (MnSOD) expression: activation of CREB and FOXO3a by PKC-alpha phosphorylation and by PKC-mediated inactivation of Akt, respectively. | 2011 Aug 26 |
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| Cellular iron depletion weakens induction of heme oxygenase-1 by cadmium. | 2011 Jan |
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| Signaling cascades mediate astrocyte death induced by zinc. | 2011 Jul 28 |
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| Involvement of H-Ras and reactive oxygen species in proinflammatory cytokine-induced matrix metalloproteinase-13 expression in human articular chondrocytes. | 2011 Mar 15 |
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| Lipid raft-dependent death receptor 5 (DR5) expression and activation are critical for ursodeoxycholic acid-induced apoptosis in gastric cancer cells. | 2011 May |
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| Arsenic-induced alteration in intracellular calcium homeostasis induces head kidney macrophage apoptosis involving the activation of calpain-2 and ERK in Clarias batrachus. | 2011 Oct 1 |
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| Time-dependent stabilization of hypoxia inducible factor-1α by different intracellular sources of reactive oxygen species. | 2012 |
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| Cigarette smoke affects keratinocytes SRB1 expression and localization via H2O2 production and HNE protein adducts formation. | 2012 |
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| Activation of CD40 with platelet derived CD154 promotes reactive oxygen species dependent death of human hepatocytes during hypoxia and reoxygenation. | 2012 |
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| Manganese promotes increased formation of hydrogen peroxide by activated human macrophages and neutrophils in vitro. | 2012 Aug |
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| Cadmium increases HIF-1 and VEGF expression through ROS, ERK, and AKT signaling pathways and induces malignant transformation of human bronchial epithelial cells. | 2012 Jan |
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| Cyclooxygenase-2 expression is up-regulated by 2-aminobiphenyl in a ROS and MAPK-dependent signaling pathway in a bladder cancer cell line. | 2012 Mar 19 |
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| TNF-Α may mediate inflammasome activation in the absence of bacterial infection in more than one way. | 2013 |
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| Contribution of NADPH oxidase to membrane CD38 internalization and activation in coronary arterial myocytes. | 2013 |
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| Ethanol increases matrix metalloproteinase-12 expression via NADPH oxidase-dependent ROS production in macrophages. | 2013 Nov 15 |
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| NADPH oxidase/ROS-dependent PYK2 activation is involved in TNF-α-induced matrix metalloproteinase-9 expression in rat heart-derived H9c2 cells. | 2013 Oct 15 |
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| Toll-like receptor 4-mediated ROS signaling pathway involved in Ganoderma atrum polysaccharide-induced tumor necrosis factor-α secretion during macrophage activation. | 2014 Apr |
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| Oxidative stress parameters induced by exposure to either cadmium or 17β-estradiol on Mytilus galloprovincialis hemocytes. The role of signaling molecules. | 2014 Jan |
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| Air pollution upregulates endothelial cell procoagulant activity via ultrafine particle-induced oxidant signaling and tissue factor expression. | 2014 Jul |
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| Purinergic signaling via P2X7 receptor mediates IL-1β production in Kupffer cells exposed to silica nanoparticle. | 2014 Jul 3 |
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| Cadmium induces matrix metalloproteinase-9 expression via ROS-dependent EGFR, NF-кB, and AP-1 pathways in human endothelial cells. | 2015 Dec 2 |
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| Endosulfan induces COX-2 expression via NADPH oxidase and the ROS, MAPK, and Akt pathways. | 2015 Nov |
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| Structurally related ganoderic acids induce apoptosis in human cervical cancer HeLa cells: Involvement of oxidative stress and antioxidant protective system. | 2015 Oct 5 |
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| Enhanced NADPH oxidases and reactive oxygen species in the mechanism of methanol-initiated protein oxidation and embryopathies in vivo and in embryo culture. | 2016 Mar |
Patents
Sample Use Guides
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
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.
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2733504
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DTXSID00196932
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4673-26-1
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7M9D81YZ2N
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77967
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ACTIVE MOIETY
SUBSTANCE RECORD
