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66-76-2,MFCD00006857
Catalog No.:AA003PB9

66-76-2 | Dicumarol

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1g
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$29.00   $20.00
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5g
98%
in stock  
$54.00   $38.00
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10g
≥98%
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$95.00   $66.00
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25g
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100g
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003PB9
Chemical Name:
Dicumarol
CAS Number:
66-76-2
Molecular Formula:
C19H12O6
Molecular Weight:
336.2950
MDL Number:
MFCD00006857
SMILES:
O=c1oc2ccccc2c(c1Cc1c(=O)oc2c(c1O)cccc2)O
Properties
Properties
 
BP:
620.702°C at 760 mmHg  
Form:
Solid  
MP:
289-291°C  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
605  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
2.6  

Literature

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Journal: Chemical research in toxicology 20180219

Title: Development of pyridine dicoumarols as potent anti HIV-1 leads, targeting HIV-1 associated topoisomeraseIIβ kinase.

Journal: Future medicinal chemistry 20170901

Title: NAD(P)H-dependent quinone oxidoreductase 1 (NQO1) and cytochrome P450 oxidoreductase (CYP450OR) differentially regulate menadione-mediated alterations in redox status, survival and metabolism in pancreatic β-cells.

Journal: Toxicology letters 20161116

Title: Study of Bioreductive Anticancer Agent RH-1-Induced Signals Leading the Wild-Type p53-Bearing Lung Cancer A549 Cells to Apoptosis.

Journal: Chemical research in toxicology 20160119

Title: Arsenic trioxide induces apoptosis in human platelets via C-Jun NH2-terminal kinase activation.

Journal: PloS one 20140101

Title: Areca nut components affect COX-2, cyclin B1/cdc25C and keratin expression, PGE2 production in keratinocyte is related to reactive oxygen species, CYP1A1, Src, EGFR and Ras signaling.

Journal: PloS one 20140101

Title: 6-Bromo-8-(4-[(3)H]methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic Acid: a powerful tool for studying orphan G protein-coupled receptor GPR35.

Journal: Journal of medicinal chemistry 20130912

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Impairment of antioxidant defenses as a contributor to arsenite-induced cell transformation.

Journal: Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine 20121001

Title: Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular generation of superoxide.

Journal: Journal of medicinal chemistry 20120823

Title: Protective effects of nicotine against aminochrome-induced toxicity in substantia nigra derived cells: implications for Parkinson's disease.

Journal: Neurotoxicity research 20120801

Title: NAD(P)H:quinone oxidoreductase 1 is induced by progesterone in cardiomyocytes.

Journal: Cardiovascular toxicology 20120601

Title: Photovoltaic and electrocatalytic properties of novel ball-type phthalocyanines bridged with four dicumarol.

Journal: Dalton transactions (Cambridge, England : 2003) 20120507

Title: Interference of H-bonding and substituent effects in nitro- and hydroxy-substituted salicylaldehydes.

Journal: Journal of molecular modeling 20120101

Title: Melt analysis of mismatch amplification mutation assays (Melt-MAMA): a functional study of a cost-effective SNP genotyping assay in bacterial models.

Journal: PloS one 20120101

Title: [Structure and properties of proprotein convertase inhibitors].

Journal: Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20120101

Title: Discovery of 2-(4-methylfuran-2(5H)-ylidene)malononitrile and thieno[3,2-b]thiophene-2-carboxylic acid derivatives as G protein-coupled receptor 35 (GPR35) agonists.

Journal: Journal of medicinal chemistry 20111027

Title: Cross talk between keratinocytes and dendritic cells: impact on the prediction of sensitization.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20111001

Title: Inhibition of renal NQO1 activity by dicoumarol suppresses nitroreduction of aristolochic acid I and attenuates its nephrotoxicity.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20110801

Title: Xylarenones C-E from an endophytic fungus isolated from Alibertia macrophylla.

Journal: Journal of natural products 20110624

Title: Autophagy protects against aminochrome-induced cell death in substantia nigra-derived cell line.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20110601

Title: In vitro genotoxicity of danthron and its potential mechanism.

Journal: Mutation research 20110518

Title: Genetic evidence for NAD(P)H:quinone oxidoreductase 1-catalyzed quinone reduction on passage through the mouse pulmonary circulation.

Journal: American journal of physiology. Lung cellular and molecular physiology 20110501

Title: Design, synthesis, and evaluation of coumarin-based molecular probes for imaging of myelination.

Journal: Journal of medicinal chemistry 20110414

Title: Comparative genomics and functional analysis of niche-specific adaptation in Pseudomonas putida.

Journal: FEMS microbiology reviews 20110301

Title: Inhibitors of NQO1: identification of compounds more potent than dicoumarol without associated off-target effects.

Journal: Biochemical pharmacology 20110201

Title: Internal mammary artery dilatation in a patient with aortic coarctation, aortic stenosis, and coronary disease. Case report.

Journal: Journal of cardiothoracic surgery 20110101

Title: β-Lapachone induces heart morphogenetic and functional defects by promoting the death of erythrocytes and the endocardium in zebrafish embryos.

Journal: Journal of biomedical science 20110101

Title: Dicoumarol activates Ca2+-permeable cation channels triggering erythrocyte cell membrane scrambling.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20110101

Title: Identification of novel species-selective agonists of the G-protein-coupled receptor GPR35 that promote recruitment of β-arrestin-2 and activate Gα13.

Journal: The Biochemical journal 20101215

Title: Cost-effective interrogation of single nucleotide polymorphisms using the mismatch amplification mutation assay and capillary electrophoresis.

Journal: Electrophoresis 20101201

Title: Protective effect of sulforaphane against cisplatin-induced mitochondrial alterations and impairment in the activity of NAD(P)H: quinone oxidoreductase 1 and γ glutamyl cysteine ligase: studies in mitochondria isolated from rat kidney and in LLC-PK1 cells.

Journal: Toxicology letters 20101110

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: A combined spectroscopic and crystallographic approach to probing drug-human serum albumin interactions.

Journal: Bioorganic & medicinal chemistry 20101101

Title: Prostate cancer radiosensitization through poly(ADP-Ribose) polymerase-1 hyperactivation.

Journal: Cancer research 20101015

Title: Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines.

Journal: Chemico-biological interactions 20101006

Title: Pharmacological inhibitors of NAD(P)H quinone oxidoreductase, NQO1: structure/activity relationships and functional activity in tumour cells.

Journal: Biochemical pharmacology 20101001

Title: Effect of cytochrome P450 and aldo-keto reductase inhibitors on progesterone inactivation in primary bovine hepatic cell cultures.

Journal: Journal of dairy science 20101001

Title: Multiple neurotrophic effects of VEGF on cultured neurons.

Journal: Neuropeptides 20100801

Title: Mechanisms of the different DNA adduct forming potentials of the urban air pollutants 2-nitrobenzanthrone and carcinogenic 3-nitrobenzanthrone.

Journal: Chemical research in toxicology 20100719

Title: Iron deficiency induces changes in riboflavin secretion and the mitochondrial electron transport chain in hairy roots of Hyoscyamus albus.

Journal: Journal of plant physiology 20100715

Title: Dicoumarol enhances gemcitabine-induced cytotoxicity in high NQO1-expressing cholangiocarcinoma cells.

Journal: World journal of gastroenterology 20100521

Title: Evidence for NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated quinone-dependent redox cycling via plasma membrane electron transport: A sensitive cellular assay for NQO1.

Journal: Free radical biology & medicine 20100201

Title: Evaluation of selective competitive binding of basic drugs to alpha1-acid glycoprotein variants.

Journal: Biological & pharmaceutical bulletin 20100101

Title: Finding new enzymes from bacterial physiology: a successful approach illustrated by the detection of novel oxidases in Marinomonas mediterranea.

Journal: Marine drugs 20100101

Title: Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: quinone oxidoreductase-1 (NQO1).

Journal: Journal of medicinal chemistry 20091126

Title: Real-time detection of cofactor availability in genetically modified living Saccharomyces cerevisiae cells--simultaneous probing of different geno- and phenotypes.

Journal: Bioelectrochemistry (Amsterdam, Netherlands) 20090901

Title: Low levels of the air pollutant 1-nitropyrene induce DNA damage, increased levels of reactive oxygen species and endoplasmic reticulum stress in human endothelial cells.

Journal: Toxicology 20090728

Title: The role of aryl hydrocarbon receptor in regulation of enzymes involved in metabolic activation of polycyclic aromatic hydrocarbons in a model of rat liver progenitor cells.

Journal: Chemico-biological interactions 20090715

Title: NAD(P)H quinone oxidoreductase 1 is essential for ozone-induced oxidative stress in mice and humans.

Journal: American journal of respiratory cell and molecular biology 20090701

Title: A new dicoumarin and anticoagulant activity from Viola yedoensis Makino.

Journal: Fitoterapia 20090701

Title: Copper dopamine complex induces mitochondrial autophagy preceding caspase-independent apoptotic cell death.

Journal: The Journal of biological chemistry 20090515

Title: Discovering chemical modifiers of oncogene-regulated hematopoietic differentiation.

Journal: Nature chemical biology 20090401

Title: Energy generation coupled to azoreduction by membranous vesicles from Shewanella decolorationis S12.

Journal: Journal of microbiology and biotechnology 20090101

Title: Analysis of couch position tolerance limits to detect mistakes in patient setup.

Journal: Journal of applied clinical medical physics 20090101

Title: [Cytotoxicity of troglitazone, structural analogue of alpha-tocopherol is mediated by inhibition of NAD(P)H:quinone oxidoreductase].

Journal: Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20090101

Title: Atom- and bond-based 2D TOMOCOMD-CARDD approach and ligand-based virtual screening for the drug discovery of new tyrosinase inhibitors.

Journal: Journal of biomolecular screening 20081201

Title: Synthesis, structure, antimicrobial and antioxidant investigations of dicoumarol and related compounds.

Journal: European journal of medicinal chemistry 20081101

Title: Discovery of novel nitrobenzothiazole inhibitors for Mycobacterium tuberculosis ATP phosphoribosyl transferase (HisG) through virtual screening.

Journal: Journal of medicinal chemistry 20081009

Title: Differential enzymatic reductions governing the differential hypoxia-selective cytotoxicities of phenazine 5,10-dioxides.

Journal: Chemical research in toxicology 20080901

Title: [Metabolism of nicousamide in rat and human liver in vitro].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20080901

Title: Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives.

Journal: European journal of medicinal chemistry 20080401

Title: Contribution of mitochondrial GSH transport to matrix GSH status and colonic epithelial cell apoptosis.

Journal: Free radical biology & medicine 20080301

Title: Regulation of inflammation signalling by resveratrol in human chondrocytes in vitro.

Journal: Biochemical pharmacology 20080201

Title: VKORC1: a warfarin-sensitive enzyme in vitamin K metabolism and biosynthesis of vitamin K-dependent blood coagulation factors.

Journal: Vitamins and hormones 20080101

Title: [Monitoring age-dependent effect of anticoagulation treatment in patients with atrial fibrillation].

Journal: Vnitrni lekarstvi 20080101

Title: The catecholaminergic RCSN-3 cell line: a model to study dopamine metabolism.

Journal: Neurotoxicity research 20080101

Title: NADPH-dependent coenzyme Q reductase is the main enzyme responsible for the reduction of non-mitochondrial CoQ in cells.

Journal: BioFactors (Oxford, England) 20080101

Title: Coumarin-based inhibitors of human NAD(P)H:quinone oxidoreductase-1. Identification, structure-activity, off-target effects and in vitro human pancreatic cancer toxicity.

Journal: Journal of medicinal chemistry 20071213

Title: Capsaicin induces heme oxygenase-1 expression in HepG2 cells via activation of PI3K-Nrf2 signaling: NAD(P)H:quinone oxidoreductase as a potential target.

Journal: Antioxidants & redox signaling 20071201

Title: Syntheses, characterization and fluorescent properties of two triethylene-glycol dicoumarin-3-carboxylates.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20071101

Title: Inhibition of ERK and JNK decreases both osmosensitive taurine release and cell proliferation in glioma cells.

Journal: Neurochemical research 20071101

Title: Role of NAD(P)H:quinone oxidoreductase 1 on tumor necrosis factor-alpha-induced migration of human vascular smooth muscle cells.

Journal: Cardiovascular research 20071101

Title: Inhibition of VMAT-2 and DT-diaphorase induce cell death in a substantia nigra-derived cell line--an experimental cell model for dopamine toxicity studies.

Journal: Chemical research in toxicology 20070501

Title: Synthesis and structure-activity relationships of novel warfarin derivatives.

Journal: Bioorganic & medicinal chemistry 20070315

Title: Lot6p from Saccharomyces cerevisiae is a FMN-dependent reductase with a potential role in quinone detoxification.

Journal: The FEBS journal 20070301

Title: Dicoumarol impairs mitochondrial electron transport and pyrimidine biosynthesis in human myeloid leukemia HL-60 cells.

Journal: Biochemical pharmacology 20070201

Title: Identification of a novel intestinal first pass metabolic pathway: NQO1 mediated quinone reduction and subsequent glucuronidation.

Journal: Current drug metabolism 20070201

Title: [Metabolism of mitomycin C by human liver microsomes in vitro].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20070201

Title: In silico identification and biochemical characterization of novel inhibitors of NQO1.

Journal: Bioorganic & medicinal chemistry letters 20061215

Title: Mitochondrial production of reactive oxygen species mediate dicumarol-induced cytotoxicity in cancer cells.

Journal: The Journal of biological chemistry 20061208

Title: From gamma-carboxy-glutamate to protein C.

Journal: Journal of thrombosis and haemostasis : JTH 20061201

Title: [Anaerobic humus respiration by Shewanella cinica D14T].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20061201

Title: Biochemical basis of 4-hydroxyanisole induced cell toxicity towards B16-F0 melanoma cells.

Journal: Cancer letters 20061118

Title: [Proteus penneri].

Journal: Enfermedades infecciosas y microbiologia clinica 20061001

Title: Arsenite pretreatment enhances the cytotoxicity of mitomycin C in human cancer cell lines via increased NAD(P)H quinone oxidoreductase 1 expression.

Journal: Toxicology and applied pharmacology 20060801

Title: Molecular cloning of a novel type of rat cytoplasmic 17beta-hydroxysteroid dehydrogenase distinct from the type 5 isozyme.

Journal: Journal of biochemistry 20060601

Title: The crystal structure of NAD(P)H quinone oxidoreductase 1 in complex with its potent inhibitor dicoumarol.

Journal: Biochemistry 20060523

Title: Dicoumarol potentiates cisplatin-induced apoptosis mediated by c-Jun N-terminal kinase in p53 wild-type urogenital cancer cell lines.

Journal: Oncogene 20060420

Title: Coenzyme Q(1) depletes NAD(P)H and impairs recycling of ascorbate in astrocytes.

Journal: Brain research 20060317

Title: Reduction of nitroaromatic compounds by NAD(P)H:quinone oxidoreductase (NQO1): the role of electron-accepting potency and structural parameters in the substrate specificity.

Journal: Acta biochimica Polonica 20060101

Title: Platelet-rich plasma treatment and hemostasis in patients with hemorrhagic risk.

Journal: Minerva stomatologica 20060101

Title: Aerobic 2- and 4-nitroreduction of CB 1954 by human liver.

Journal: Toxicology 20051215

Title: Heat-induced up-regulation of NAD(P)H:quinone oxidoreductase potentiates anticancer effects of beta-lapachone.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20051215

Title: Biochemical characterization of trinitrotoluene transforming oxygen-insensitive nitroreductases from Clostridium acetobutylicum ATCC 824.

Journal: Archives of microbiology 20051101

Title: Involvement of carbonyl reductase in superoxide formation through redox cycling of adrenochrome and 9,10-phenanthrenequinone in pig heart.

Journal: Chemico-biological interactions 20050815

Title: Mechanism of cell cycle regulation by FIP200 in human breast cancer cells.

Journal: Cancer research 20050801

Title: Xanthohumol isolated from Humulus lupulus Inhibits menadione-induced DNA damage through induction of quinone reductase.

Journal: Chemical research in toxicology 20050801

Title: Human NAD(P)H:quinone oxidoreductase inhibition by flavonoids in living cells.

Journal: Free radical biology & medicine 20050715

Title: Dicoumarol relieves serum withdrawal-induced G0/1 blockade in HL-60 cells through a superoxide-dependent mechanism.

Journal: Biochemical pharmacology 20050601

Title: Enzymatic properties of a member (AKR1C19) of the aldo-keto reductase family.

Journal: Biological & pharmaceutical bulletin 20050601

Title: Environmental pollutant and potent mutagen 3-nitrobenzanthrone forms DNA adducts after reduction by NAD(P)H:quinone oxidoreductase and conjugation by acetyltransferases and sulfotransferases in human hepatic cytosols.

Journal: Cancer research 20050401

Title: 20S proteasomal degradation of ornithine decarboxylase is regulated by NQO1.

Journal: Molecular cell 20050304

Title: Monoamine transporter inhibitors and norepinephrine reduce dopamine-dependent iron toxicity in cells derived from the substantia nigra.

Journal: Journal of neurochemistry 20050301

Title: Dopamine-dependent iron toxicity in cells derived from rat hypothalamus.

Journal: Chemical research in toxicology 20050301

Title: Dicumarol is a potent reversible inhibitor of gap junctional intercellular communication.

Journal: Archives of biochemistry and biophysics 20050215

Title: Enhanced cytotoxicity of bioreductive antitumor agents with dimethyl fumarate in human glioblastoma cells.

Journal: Anti-cancer drugs 20050201

Title: Baicalein protects rat cardiomyocytes from hypoxia/reoxygenation damage via a prooxidant mechanism.

Journal: Cardiovascular research 20050101

Title: Susceptibility of cancer cells to beta-lapachone is enhanced by ionizing radiation.

Journal: International journal of radiation oncology, biology, physics 20050101

Title: Tanshinone IIA isolated from Salvia miltiorrhiza elicits the cell death of human endothelial cells.

Journal: Journal of biomedical science 20050101

Title: Mechanical valve replacement in congenital heart defects in the era of international normalized ratio self-management.

Journal: ASAIO journal (American Society for Artificial Internal Organs : 1992) 20050101

Title: Mechanism to study 1:1 stoichiometry of NADPH and alkoxyphenoxazones metabolism spectrophotometrically in subcellular biological preparations.

Journal: Biochimica et biophysica acta 20041118

Title: Dietary induction of NQO1 increases the antitumour activity of mitomycin C in human colon tumours in vivo.

Journal: British journal of cancer 20041018

Title: Gene- and cell-type-specific effects of signal transduction cascades on metal-regulated gene transcription appear to be independent of changes in the phosphorylation of metal-response-element-binding transcription factor-1.

Journal: The Biochemical journal 20040815

Title: Gastrodia elata prevents rat pheochromocytoma cells from serum-deprived apoptosis: the role of the MAPK family.

Journal: Life sciences 20040813

Title: Synthesis and urease enzyme inhibitory effects of some dicoumarols.

Journal: Journal of enzyme inhibition and medicinal chemistry 20040801

Title: Treatment of pancreatic cancer cells with dicumarol induces cytotoxicity and oxidative stress.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040701

Title: Dicumarol, an inhibitor of ADP-ribosylation of CtBP3/BARS, fragments golgi non-compact tubular zones and inhibits intra-golgi transport.

Journal: European journal of cell biology 20040701

Title: Cell surface oxygen consumption by mitochondrial gene knockout cells.

Journal: Biochimica et biophysica acta 20040607

Title: Rescue of TNFalpha-inhibited neuronal cells by IGF-1 involves Akt and c-Jun N-terminal kinases.

Journal: Journal of neuroscience research 20040515

Title: JNK activation is a mediator of arsenic trioxide-induced apoptosis in acute promyelocytic leukemia cells.

Journal: Blood 20040501

Title: NAD(P)H:quinone oxidoreductase-1-dependent and -independent cytotoxicity of potent quinone Cdc25 phosphatase inhibitors.

Journal: The Journal of pharmacology and experimental therapeutics 20040401

Title: Geomorphological evolution and environmental reclamation of Fusaro Lagoon (Campania Province, southern Italy).

Journal: Environment international 20040401

Title: Characterization and molecular cloning of a glutathione S-transferase from the whitefly Bemisia tabaci (Hemiptera: Aleyrodidae).

Journal: Insect biochemistry and molecular biology 20040401

Title: Effects of 17-beta estradiol and 4-nonylphenol on phase II electrophilic detoxification pathways in largemouth bass (Micropterus salmoides) liver.

Journal: Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20040301

Title: Dicoumarol alters cellular redox state and inhibits nuclear factor kappa B to enhance arsenic trioxide-induced apoptosis.

Journal: Acta biochimica et biophysica Sinica 20040301

Title: Specific ligand binding on genetic variants of human alpha1-acid glycoprotein studied by circular dichroism spectroscopy.

Journal: Biochemical pharmacology 20040215

Title: Behavioral effects of manganese injected in the rat substantia nigra are potentiated by dicumarol, a DT-diaphorase inhibitor.

Journal: Pharmacology, biochemistry, and behavior 20040201

Title: Quinones and glutathione metabolism.

Journal: Methods in enzymology 20040101

Title: NAD(P)H:quinone oxidoreductase 1 expression, hydrogen peroxide levels, and growth phase in HeLa cells.

Journal: Methods in enzymology 20040101

Title: p53-dependent apoptosis and NAD(P)H:quinone oxidoreductase 1.

Journal: Methods in enzymology 20040101

Title: Effects of the DT-diaphorase inhibitor dicumarol on striatal monoamine levels in L-DOPA and L-deprenyl pre-treated rats.

Journal: Neurotoxicity research 20040101

Title: Inhibition of DT-diaphorase potentiates the in vivo neurotoxic effect of intranigral injection of salsolinol in rats.

Journal: Neurotoxicity research 20040101

Title: [Superior vena cava thrombosis in a patient on hemodialysis].

Journal: Nefrologia : publicacion oficial de la Sociedad Espanola Nefrologia 20040101

Title: P53 hot-spot mutants are resistant to ubiquitin-independent degradation by increased binding to NAD(P)H:quinone oxidoreductase 1.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20031209

Title: Menadione enhances oxyradical formation in earthworm extracts: vulnerability of earthworms to quinone toxicity.

Journal: Aquatic toxicology (Amsterdam, Netherlands) 20031008

Title: Inhibition of the SAPK/JNK pathway blocks the stimulatory effects of glutamine on fluid secretion by the Malpighian tubules of Rhodnius prolixus.

Journal: Journal of insect physiology 20031001

Title: Studies on the nitroreductase prodrug-activating system. Crystal structures of complexes with the inhibitor dicoumarol and dinitrobenzamide prodrugs and of the enzyme active form.

Journal: Journal of medicinal chemistry 20030911

Title: Dicumarol inhibition of NADPH:quinone oxidoreductase induces growth inhibition of pancreatic cancer via a superoxide-mediated mechanism.

Journal: Cancer research 20030901

Title: Cytotoxicity of RH1 and related aziridinylbenzoquinones: involvement of activation by NAD(P)H:quinone oxidoreductase (NQO1) and oxidative stress.

Journal: Archives of biochemistry and biophysics 20030801

Title: Improving relative bioavailability of dicumarol by reducing particle size and adding the adhesive poly(fumaric-co-sebacic) anhydride.

Journal: Pharmaceutical research 20030701

Title: AMP-activated protein kinase can induce apoptosis of insulin-producing MIN6 cells through stimulation of c-Jun-N-terminal kinase.

Journal: Journal of molecular endocrinology 20030401

Title: Recruitment of the interleukin-1 receptor (IL-1RI)-associated kinase IRAK to the IL-1RI is redox regulated.

Journal: Biological chemistry 20030401

Title: Dicoumarol: a unique microtubule stabilizing natural product that is synergistic with Taxol.

Journal: Cancer research 20030315

Title: Role of NAD(P)H:quinone oxidoreductase in the progression of neuronal cell death in vitro and following cerebral ischaemia in vivo.

Journal: Journal of neurochemistry 20030301

Title: Reactive quinones differentially regulate SAPK/JNK and p38/mHOG stress kinases.

Journal: Antioxidants & redox signaling 20030201

Title: Hepatocyte metabolism of coenzyme Q1 (ubiquinone-5) to its sulfate conjugate decreases its antioxidant activity.

Journal: BioFactors (Oxford, England) 20030101

Title: Antioxidant response induced by serum withdrawal protects HL-60 cells against inhibition of NAD(P)H:quinone oxidoreductase 1.

Journal: BioFactors (Oxford, England) 20030101

Title: MPP(+)-induced degeneration is potentiated by dicoumarol in cultures of the RCSN-3 dopaminergic cell line. Implications of neuromelanin in oxidative metabolism of dopamine neurotoxicity.

Journal: Neurotoxicity research 20030101

Title: Structural and drug-binding properties of alpha(1)-acid glycoprotein in reverse micelles.

Journal: Biochimica et biophysica acta 20021216

Title: A physiological threshold for protection against menadione toxicity by human NAD(P)H:quinone oxidoreductase (NQO1) in Chinese hamster ovary (CHO) cells.

Journal: Biochemical pharmacology 20021201

Title: Insulin-like growth factor-1 activates Akt and Jun N-terminal kinases (JNKs) in promoting the survival of T lymphocytes.

Journal: Immunology 20021201

Title: CNS neurons express two distinct plasma membrane electron transport systems implicated in neuronal viability.

Journal: Journal of neurochemistry 20021101

Title: A novel plasma membrane quinone reductase and NAD(P)H:quinone oxidoreductase 1 are upregulated by serum withdrawal in human promyelocytic HL-60 cells.

Journal: Journal of bioenergetics and biomembranes 20020601

Title: Effect of dicumarol, a Nad(P)h: quinone acceptor oxidoreductase 1 (DT-diaphorase) inhibitor on ubiquinone redox cycling in cultured rat hepatocytes.

Journal: Free radical research 20020401

Title: Enhanced activity of the plasma membrane oxidoreductase in circulating lymphocytes from insulin-dependent diabetes mellitus patients.

Journal: Biochemical and biophysical research communications 20020208

Title: NAD(P)H: quinone oxidoreductase enhances proliferation inhibition by 4-hydroxytamoxifen.

Journal: Anticancer research 20020101

Title: Dicoumarol toxicity in cattle associated with ingestion of silage containing sweet vernal grass (Anthoxanthum odoratum).

Journal: Australian veterinary journal 20020101

Title: Mitomycin C-induced cell death in mouse lens epithelial cells.

Journal: Ophthalmic research 20020101

Title: Expression of NAD(P)H:quinone oxidoreductase 1 in HeLa cells: role of hydrogen peroxide and growth phase.

Journal: The Journal of biological chemistry 20011130

Title: Phosphorylation is involved in the activation of metal-regulatory transcription factor 1 in response to metal ions.

Journal: The Journal of biological chemistry 20011109

Title: The oral anticoagulant saga: past, present, and future.

Journal: Clinical and applied thrombosis/hemostasis : official journal of the International Academy of Clinical and Applied Thrombosis/Hemostasis 20011001

Title: Concerted action of DT-diaphorase and superoxide dismutase in preventing redox cycling of naphthoquinones: an evaluation.

Journal: Free radical research 20010801

Title: beta-Lapachone-induced apoptosis in human prostate cancer cells: involvement of NQO1/xip3.

Journal: Experimental cell research 20010701

Title: Piperidinium 3-[(4-hydroxy-5-dimethyl-2-oxo-2H-chromen-3-yl)-phenylmethyl]-5,7-dimethyl-2-oxo-2H-chromen-4-olate.

Journal: Acta crystallographica. Section C, Crystal structure communications 20010701

Title: Bioreductive metabolism of mitomycin C in EMT6 mouse mammary tumor cells: cytotoxic and non-cytotoxic pathways, leading to different types of DNA adducts. The effect of dicumarol.

Journal: Biochemical pharmacology 20010615

Title: Transient activation of Jun N-terminal kinases and protection from apoptosis by the insulin-like growth factor I receptor can be suppressed by dicumarol.

Journal: The Journal of biological chemistry 20010601

Title: Possible role of salsolinol quinone methide in the decrease of RCSN-3 cell survival.

Journal: Biochemical and biophysical research communications 20010525

Title: The role of glutathione reductase in the cytotoxicity of chromium (VI) in isolated rat hepatocytes.

Journal: Chemico-biological interactions 20010416

Title: Copper neurotoxicity is dependent on dopamine-mediated copper uptake and one-electron reduction of aminochrome in a rat substantia nigra neuronal cell line.

Journal: Journal of neurochemistry 20010401

Title: Effects of modulation of tissue activities of DT-diaphorase on the toxicity of 2,3-dimethyl-1,4-naphthoquinone to rats.

Journal: Chemico-biological interactions 20010314

Title: Reactive oxygen species from NAD(P)H:quinone oxidoreductase constitutively activate NF-kappaB in malignant melanoma cells.

Journal: American journal of physiology. Cell physiology 20010301

Title: Reactive oxygen species regulate signaling pathways induced by M1 muscarinic receptors in PC12M1 cells.

Journal: Journal of neurochemistry 20010301

Title: [Incidence of tumors after treatment with oral anticoagulants].

Journal: Strahlentherapie und Onkologie : Organ der Deutschen Rontgengesellschaft ... [et al] 20010201

Title: Inhibition of trans-membrane hexacyanoferrate III reductase activity and proton secretion of maize (Zea mays L.) roots by thenoyltrifluoroacetone.

Journal: Protoplasma 20010101

Title: Interaction between electron transport at the plasma membrane and nitrate uptake by maize (Zea mays L.) roots.

Journal: Protoplasma 20010101

Title: NAD(P)H:quinone oxidoreductase (NQO1) protects astroglial cells against L-dopa toxicity.

Journal: Advances in experimental medicine and biology 20010101

Title: NRH:quinone oxidoreductase2 (NQO2).

Journal: Chemico-biological interactions 20001201

Title: Coumarin derivatives and breast-feeding.

Journal: Obstetrics and gynecology 20000601

Title: Chromium (VI)-induced cytotoxicity to osteoblast-derived cells.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 19991201

Title: Quinone reductase inhibitors block SAPK/JNK and NFkappaB pathways and potentiate apoptosis.

Journal: The Journal of biological chemistry 19991029

Title: Modulation of halobenzene-induced hepatotoxicity by DT-diaphorase modulators, butylated hydroxyanisole and dicoumarol: evidence for possible involvement of quinone metabolites in the toxicity of halobenzenes.

Journal: Toxicology letters 19990308

Title: Fulminant hepatic failure associated with dicoumarol therapy.

Journal: Liver 19980201

Title: Enhanced renal vitamin-K-dependent gamma-glutamyl carboxylase activity in experimental rat urolithiasis.

Journal: European urology 19980101

Title: The role of NAD(P)H:quinone oxidoreductase in quinone-mediated p21 induction in human colon carcinoma cells.

Journal: Archives of biochemistry and biophysics 19971015

Title: Roles of DT diaphorase in the genotoxicity of nitroaromatic compounds in human and fish cell lines.

Journal: Journal of toxicology and environmental health 19971010

Title: Coumarin-based inhibitors of HIV integrase.

Journal: Journal of medicinal chemistry 19970117

Title: Induction of p21 mediated by reactive oxygen species formed during the metabolism of aziridinylbenzoquinones by HCT116 cells.

Journal: The Journal of biological chemistry 19961213

Title: Inhibition kinetics of camel lens zeta-crystallin: multiple inhibition studies.

Journal: Journal of enzyme inhibition 19960801

Title: Antiretroviral agents as inhibitors of both human immunodeficiency virus type 1 integrase and protease.

Journal: Journal of medicinal chemistry 19960621

Title: Discovery of novel, non-peptide HIV-1 protease inhibitors by pharmacophore searching.

Journal: Journal of medicinal chemistry 19960510

Title: Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations.

Journal: British journal of cancer 19950401

Title: Aspirin-like drugs can protect human T lymphocytes against benzoquinone cytotoxicity: evidence for a NAD(P)H:quinone reductase-dependent mechanism.

Journal: Archives of toxicology 19950101

Title: Reduction of chromium(VI) to chromium(V) by rat liver cytosolic and microsomal fractions: is DT-diaphorase involved?

Journal: Carcinogenesis 19920701

Title: [Fatal cerebral hemorrhage caused by overdose of dicumarol, report of a case].

Journal: Anales de medicina interna (Madrid, Spain : 1984) 19920201

Title: Identification and characterization of the enzymatic activity of zeta-crystallin from guinea pig lens. A novel NADPH:quinone oxidoreductase.

Journal: The Journal of biological chemistry 19920105

Title: Dicoumarol and warfarin.

Journal: British heart journal 19910801

Title: Metabolism of mitomycin C by DT-diaphorase: role in mitomycin C-induced DNA damage and cytotoxicity in human colon carcinoma cells.

Journal: Cancer research 19901201

Title: Activation and deactivation of quinones catalyzed by DT-diaphorase. Evidence for bioreductive activation of diaziquone (AZQ) in human tumor cells and detoxification of benzene metabolites in bone marrow stroma.

Journal: Free radical research communications 19900101

Title: In-vivo effects of itraconazole on hepatic mixed-function oxidase.

Journal: The Journal of antimicrobial chemotherapy 19880201

Title: Spontaneous anticoagulant-induced hemopericardium with tamponade.

Journal: Acta haematologica 19820101

Title: Disseminated intravascular coagulation induced by progesterone in the pregnant rat. Prevention by estogens.

Journal: The American journal of pathology 19770301

Title: Pineal apoplexy associated with anticoagulant therapy. Case report.

Journal: Journal of neurosurgery 19760801

Title: Comparison of graphical and computerized methods for calculating binding parameters for two strongly bound drugs to human serum albumin.

Journal: Journal of pharmaceutical sciences 19760801

Title: Impotence in patients treated with clofibrate.

Journal: Atherosclerosis 19750101

Title: Management of thrombo-embolism after aortic valve replacement with the Björk-Shiley tilting disc valve. Medicamental prevention with dicumarol in comparison with dipyridamole - acetylsalicylic acid. Surgical treatment of prosthetic thrombosis.

Journal: Scandinavian journal of thoracic and cardiovascular surgery 19750101

Title: Intraocular hemorrhage and blindness associated with systemic anticoagulation.

Journal: JAMA 19720605

Title: Unusual gastrointestinal reaction to bishydroxycoumarin(Dicumarol).

Journal: American heart journal 19680701

Title: Urinary tract complications of anticoagulation therapy; 'pseudotumour' of the kidney.

Journal: The British journal of radiology 19680301

Title: Antagonism of anticoagulants dicoumarol, tromexan, and phenylindandione by vitamin K.

Journal: British medical journal 19520927

Title: Bian J, et al. Affinity-based small fluorescent probe for NAD(P)H:quinone oxidoreductase 1 (NQO1). Design, synthesis and pharmacological evaluation. Eur J Med Chem. 2017 Feb 15;127:828-839.

Title: Zhang W, et al. Dicumarol inhibits PDK1 and targets multiple malignant behaviors of ovarian cancer cells. PLoS One. 2017 Jun 15;12(6):e0179672.

Title: Fiorillo M, et al. Mitochondrial "power" drives tamoxifen resistance: NQO1 and GCLC are new therapeutic targets in breast cancer. Oncotarget. 2017 Mar 2;8(12):20309-20327.

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Tags:66-76-2 Molecular Formula|66-76-2 MDL|66-76-2 SMILES|66-76-2 Dicumarol