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M5625 Sigma

Menadione

crystalline

Synonym: 2-Methyl-1,4-naphthoquinone, Vitamin K3

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Properties

Related Categories Biochemicals and Reagents, Cell Biology, Cell Signaling and Neuroscience, Cell Stress, Lipids,
form   crystalline
color   yellow
mp   105-107 °C(lit.)
solubility   oil: soluble
Gene Information   human ... NQO1(1728)

Description

Packaging

25, 100 g in glass bottle

Biochem/physiol Actions

Menadione (Vitamin K3) is a synthetic analogue of of 1,4-naphthoquinone with a methyl group in the 2-position. Menadione is used as a phosphatase inhibitor and an inhibitor of mitochondrial DNA polymerase γ (pol γ). Menadione can be used as an oxidative injury (free radical generator) inducing agent.

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Menadione

meets USP testing specifications

Menadione
M0300000Menadione

European Pharmacopoeia (EP) Reference Standard

Menadione
M57405Menadione

98%

Menadione (K3)

analytical standard

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36
WGK Germany 
3
RTECS 
QL9100000

Protocols & Articles

Peer-Reviewed Papers

References

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The metabolism of menadione (2-methyl-1,4-naphthoquinone) by isolated hepatocytes. Thor, H., et al. J. Biol. Chem. 257, 12419-12425, (1982)

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Clinical, histological and genetic characterization of reducing body myopathy caused by mutations in FHL1 Schessl, J., et al. Brain 132, 452-64, (2009)

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Proteomic identification of FHL1 as the protein mutated in human reducing body myopathy Judkins, A.R., et al. J. Clin. Invest. 118, 904-912, (2008)

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Ferroxitosis: A cell death from modulation of oxidative phosphorylation and PKM2-dependent glycolysis in melanoma. Lakhter AJ, Hamilton J, Dagher PC, et al. Oncotarget 5(24), 12694-703, (2014)

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A simple and reproducible 96-well plate-based method for the formation of fungal biofilms and its application to antifungal susceptibility testing. Pierce, C.G., et al. Nat. Protoc. 3, 1494-500, (2008)

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Glial cell type-specific responses to menadione-induced oxidative stress. Hollensworth, S.B., et al. Free Radic. Biol. Med. 28, 1161-1174, (2000)

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Oxidative stress-induced apoptosis of endothelial cells. Warren, M.C., et al. Free Radic. Biol. Med. 29, 537-757, (2000)

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Effects Of Hypothermic Storage On Intracellular Calcium, Reactive Oxygen Species Formation, Mitochondrial Function, Motility, And Plasma Membrane Integrity In Striped Bass (Morone Saxatilis) Sperm. Guthrie, H.D., et al. Theriogenology 75, 951-61, (2011)

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Steatosis reversibly increases hepatocyte sensitivity to hypoxia-reoxygenation injury. Berthiaume, F., et al. J. Surg. Res. 152, 54-60, (2009)

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Inhibitory effect of novel 5-O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response. Maruo S, Kuriyama I, et al Bioorg. Med. Chem. 19, 5803-5812, (2011)

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Free cholesterol accumulation impairs antioxidant activities and aggravates apoptotic cell death in menadione-induced oxidative injury. Lee W, Xu M, Li Y, Gu Y, et al. Arch. Biochem. Biophys. 514, 57-67, (2011)

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Candida albicans viability after exposure to amphotericin B: assessment using metabolic assays and colony forming units. Khot, P.D., et al. J. Microbiol. Methods 72, 268-74, (2008)

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Using Fluorescence-activated Flow Cytometry To Determine Reactive Oxygen Species Formation And Membrane Lipid Peroxidation In Viable Boar Spermatozoa. Guthrie, H.D., and Welch, G.R. Methods Mol. Biol. 594, 163-71, (2010)

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Vitamin K concentrations in the plasma and liver of surgical patients. Usui Y, Tanimura H, Nishimura N, et al. Am. J. Clin. Nutr. 51(5), 846-52, (1990)

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Role of the Mycobacterium tuberculosis P55 efflux pump in intrinsic drug resistance, oxidative stress responses, and growth. Santiago Ramón-García et al Antimicrob. Agents Chemother. 53, 3675-82, (2009)

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Carbonyl reductase provides the enzymatic basis of quinone detoxication in man. Wermuth B, Platts KL, Seidel A, et al. Biochem. Pharmacol. 35(8), 1277-82, (1986)

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Vitamin K status in human tissues: tissue-specific accumulation of phylloquinone and menaquinone-4. Thijssen HH and Drittij-Reijnders MJ Br. J. Nutr. 75(1), 121-7, (1996)

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Genome structure of a Saccharomyces cerevisiae strain widely used in bioethanol production. Argueso JL, Carazzolle MF, Mieczkowski PA, et al. Genome Res. 19(12), 2258-70, (2009)

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Triclosan-induced aminoglycoside-tolerant Listeria monocytogenes isolates can appear as small-colony variants. Kastbjerg VG, Hein-Kristensen L, and Gram L Antimicrob. Agents Chemother. 58(6), 3124-32, (2014)

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Bioactive pyridine-N-oxide disulfides from Allium stipitatum. Gemma O'Donnell et al J. Nat. Prod. 72, 360-5, (2009)

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Bioelectrochemical probing of intracellular redox processes in living yeast cells--application of redox polymer wiring in a microfluidic environment. Heiskanen A, Coman V, Kostesha N, et al. Anal. Bioanal. Chem 405(11), 3847-58, (2013)

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Novel class of quinone-bearing polyamines as multi-target-directed ligands to combat Alzheimer's disease. Maria Laura Bolognesi et al J. Med. Chem. 50, 4882-97, (2007)

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Biotransformation of polymethoxylated flavonoids: access to their 4'-O-demethylated metabolites. Didier Buisson et al J. Nat. Prod. 70, 1035-8, (2007)

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Aldehyde oxidase: an enzyme of emerging importance in drug discovery. David C Pryde et al J. Med. Chem. 53, 8441-60, (2010)

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Crystal structure of Miner1: The redox-active 2Fe-2S protein causative in Wolfram Syndrome 2. Conlan AR J. Mol. Biol. 392(1), 143-53, (2009)

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Time series analysis of oxidative stress response patterns in HepG2: a toxicogenomics approach. Deferme L, Briedé JJ, Claessen SM, et al. Toxicology 306, 24-34, (2013)

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[The role of thiol antioxidants in restoring mitochondrial functions, modified by microbial metabolites]. Fedotcheva NI, Teplova VV, and Beloborodova NV Biofizika 57(5), 820-6, (2012)

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Pharmacokinetics of vitamin K in mothers and children in the perinatal period: transplacental transport of vitamin K2 (MK-4). Iioka H, Moriyama IS, Morimoto K, et al. Asia. Oceania. J. Obstet. Gynaecol. 17(1), 97-100, (1991)

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Identification of the binding domain of Streptococcus oralis glyceraldehyde-3-phosphate dehydrogenase for Porphyromonas gingivalis major fimbriae. Nagata H Infect. Immun. 77(11), 5130-8, (2009)

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Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors. Sanjeev Kumar et al J. Med. Chem. 51, 1706-18, (2008)

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Mechanisms, biology and inhibitors of deubiquitinating enzymes. Kerry Routenberg Love et al Nat. Chem. Biol. 3, 697-705, (2007)

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A non-classical LysR-type transcriptional regulator PA2206 is required for an effective oxidative stress response in Pseudomonas aeruginosa. Reen FJ, Haynes JM, Mooij MJ, et al. PLoS ONE 8(1), e54479, (2013)

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Role of vitamin K2 in the development of hepatocellular carcinoma in women with viral cirrhosis of the liver. Habu D, Shiomi S, Tamori A, et al. JAMA 292(3), 358-61, (2004)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Biomimetic synthesis of zeylanone and zeylanone epoxide by dimerization of 2-methyl-1,4-naphthoquinone. Maruo S, Nishio K, Sasamori T, et al. Org. Lett. 15(7), 1556-9, (2013)

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A surface on the androgen receptor that allosterically regulates coactivator binding. Eva Estébanez-Perpiñá et al Proc. Natl. Acad. Sci. U. S. A. 104, 16074-9, (2007)

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Angiotensin II protects primary rat hepatocytes against bile salt-induced apoptosis. Karimian G, Buist-Homan M, Mikus B, et al. PLoS ONE 7(12), e52647, (2012)

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Developing structure-activity relationships for the prediction of hepatotoxicity. Nigel Greene et al Chem. Res. Toxicol. 23, 1215-22, (2010)

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Intracellular forms of menadione-dependent small-colony variants of methicillin-resistant Staphylococcus aureus are hypersusceptible to β-lactams in a THP-1 cell model due to cooperation between vacuolar acidic pH and oxidant species. Garcia LG, Lemaire S, Kahl BC, et al. J. Antimicrob. Chemother. 67(12), 2873-81, (2012)

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Toxicity of CuO nanoparticles to yeast Saccharomyces cerevisiae BY4741 wild-type and its nine isogenic single-gene deletion mutants. Kasemets K, Suppi S, Künnis-Beres K, et al. Chem. Res. Toxicol. 26(3), 356-67, (2013)

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Proteome changes associated with Leishmania donovani promastigote adaptation to oxidative and nitrosative stresses. Sardar AH, Kumar S, Kumar A, et al. J. Proteomics 81, 185-99, (2013)

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Measurement of immunoreactive prothrombin, des-gamma-carboxy prothrombin, and vitamin K in human liver tissues: overproduction of immunoreactive prothrombin in hepatocellular carcinoma. Ono M, Ohta H, Ohhira M, et al. Am. J. Gastroenterol. 85(9), 1149-54, (1990)

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Menadione (vitamin K3) is a catabolic product of oral phylloquinone (vitamin K1) in the intestine and a circulating precursor of tissue menaquinone-4 (vitamin K2) in rats. Hirota Y, Tsugawa N, Nakagawa K, et al. J. Biol. Chem. 288(46), 33071-80, (2013)

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A predictive ligand-based Bayesian model for human drug-induced liver injury. Sean Ekins et al Drug Metab. Dispos. 38, 2302-8, (2010)

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Calcineurin-responsive zinc finger transcription factor CRZ1 of Botrytis cinerea is required for growth, development, and full virulence on bean plants. Schumacher J Eukaryotic Cell 7(4), 584-601, (2008)

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Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase. Anita Mahapatra et al Bioorg. Med. Chem. 15, 7638-46, (2007)

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Neurovascular unit and the effects of dosage in VEGF toxicity: role for oxidative stress and thrombin. Sanchez A, Tripathy D, Luo J, et al. J. Alzheimers Dis. 34(1), 281-91, (2013)

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Signaling effects of menadione: from tyrosine phosphatase inactivation to connexin phosphorylation. Abdelmohsen K, Patak P, Von Montfort C, et al. Meth. Enzymol. 378, 258-72, (2004)

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Role of a novel dual flavin reductase (NR1) and an associated histidine triad protein (DCS-1) in menadione-induced cytotoxicity. Kwaśnicka-Crawford DA and Vincent SR Biochem. Biophys. Res. Commun. 336(2), 565-71, (2005)

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Identification of point mutations in clinical Staphylococcus aureus strains that produce small-colony variants auxotrophic for menadione. Dean MA, Olsen RJ, Long SW, et al. Infect. Immun. 82(4), 1600-5, (2014)

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Screening test for rapid food safety evaluation by menadione-catalysed chemiluminescent assay. Yamashoji S, Yoshikawa N, Kirihara M, et al. Food Chem. 138(4), 2146-51, (2013)

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In vitro activities of retigeric acid B alone and in combination with azole antifungal agents against Candida albicans. Lingmei Sun et al Antimicrob. Agents Chemother. 53, 1586-91, (2009)

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QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES. A A Toropov et al Eur. J. Med. Chem. 43, 714-40, (2008)

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Inhibition of polymorphic human carbonyl reductase 1 (CBR1) by the cardioprotectant flavonoid 7-monohydroxyethyl rutoside (monoHER). Vanessa Gonzalez-Covarrubias et al Pharm. Res. 25, 1730-4, (2010)

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Identification of potent virtual leads to design novel indoleamine 2,3-dioxygenase inhibitors: pharmacophore modeling and molecular docking studies. Shalini John et al Eur. J. Med. Chem. 45, 4004-12, (2010)

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Continuous flow-extractive desorption electrospray ionization: analysis from "non-electrospray ionization-friendly" solvents and related mechanism. Li L, Yang SH, Lemr K, et al. Anal. Chim. Acta 769, 84-90, (2013)

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Determination of the urinary aglycone metabolites of vitamin K by HPLC with redox-mode electrochemical detection. Harrington DJ, Soper R, Edwards C, et al. J. Lipid Res. 46(5), 1053-60, (2005)

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Type II NADH dehydrogenase of the respiratory chain of Plasmodium falciparum and its inhibitors. Carolyn K Dong et al Bioorg. Med. Chem. Lett. 19, 972-5, (2009)

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The 1,4-naphthoquinone scaffold in the design of cysteine protease inhibitors. Cláudia Valente et al Bioorg. Med. Chem. 15, 5340-50, (2007)

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Bioactivities of simplified adociaquinone B and naphthoquinone derivatives against Cdc25B, MKP-1, and MKP-3 phosphatases. Shugeng Cao et al Bioorg. Med. Chem. 17, 2276-81, (2009)

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Effects of glutathione and ascorbic acid on streptomycin sensitivity of Escherichia coli. Manish Goswami et al Antimicrob. Agents Chemother. 51, 1119-22, (2007)

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Characterization of clinical Enterococcus faecalis small-colony variants. Wellinghausen N J. Clin. Microbiol. 47(9), 2802-11, (2009)

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Synthesis and biological evaluation of novel heterocyclic quinones as inhibitors of the dual specificity protein phosphatase CDC25C. Olivier Lavergne et al Bioorg. Med. Chem. Lett. 16, 171-5, (2006)

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Lysosome dysfunction enhances oxidative stress-induced apoptosis through ubiquitinated protein accumulation in Hela cells. Yu C, Huang X, Xu Y, et al. Anat. Rec. (Hoboken.) 296(1), 31-9, (2013)

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Effects of low-dose ionizing radiation and menadione, an inducer of oxidative stress, alone and in combination in a vertebrate embryo model. Bladen CL, Kozlowski DJ, and Dynan WS Radiat. Res. 178(5), 499-503, (2012)

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Alpha-tocopheryl succinate inhibits autophagic survival of prostate cancer cells induced by vitamin K3 and ascorbate to trigger cell death. Tomasetti M, Nocchi L, Neuzil J, et al. PLoS ONE 7(12), e52263, (2012)

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Utilizing mitochondrial events as biomarkers for imaging apoptosis. Yivgi-Ohana N, Eifer M, Addadi Y, et al. Cell Death Dis. 2, e166, (2011)

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A biophysical approach to menadione membrane interactions: relevance for menadione-induced mitochondria dysfunction and related deleterious/therapeutic effects. Monteiro JP, Martins AF, Nunes C, et al. Biochim. Biophys. Acta 1828(8), 1899-908, (2013)

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CR108, a novel vitamin K3 derivative induces apoptosis and breast tumor inhibition by reactive oxygen species and mitochondrial dysfunction. Yang CR, Liao WS, Wu YH, et al. Toxicol. Appl. Pharmacol. 273(3), 611-22, (2013)

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Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models. Naomi L Kruhlak et al Toxicol. Mech. Methods 18, 217-27, (2008)

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S-nitrosoglutathione covalently modifies cysteine residues of human carbonyl reductase 1 and affects its activity. Hartmanová T, Tambor V, Lenčo J, et al. Chem. Biol. Interact. 202(1-3), 136-45, (2013)

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Novel phosphorylation and ubiquitination sites regulate reactive oxygen species-dependent degradation of anti-apoptotic c-FLIP protein. Wilkie-Grantham RP, Matsuzawa S, and Reed JC J. Biol. Chem. 288(18), 12777-90, (2013)

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Activation of a PGC-1-related coactivator (PRC)-dependent inflammatory stress program linked to apoptosis and premature senescence. Gleyzer N and Scarpulla RC J. Biol. Chem. 288(12), 8004-15, (2013)

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Vitamin K deficiency during the perinatal and infantile period. Suzuki S, Iwata G, and Sutor AH Semin. Thromb. Hemost. 27(2), 93-8, (2001)

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Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins. Alfonso Pérez-Garrido et al Bioorg. Med. Chem. 17, 896-904, (2009)

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Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults. Snider BJ, Moss JL, Revilla FJ, et al. Neuroscience 120(3), 617-25, (2003)

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2,3-Dimethoxy-5-methyl-1,4-benzoquinones and 2-methyl-1,4-naphthoquinones: glycation inhibitors with lipid peroxidation activity. Young-Sik Jung et al Bioorg. Med. Chem. Lett. 15, 1125-9, (2005)

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Molecular insights into human monoamine oxidase (MAO) inhibition by 1,4-naphthoquinone: evidences for menadione (vitamin K3) acting as a competitive and reversible inhibitor of MAO. Eduardo Coelho Cerqueira et al Bioorg. Med. Chem. 19, 7416-24, (2011)

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Menadione and ethacrynic acid inhibit the hypoxia-inducible factor (HIF) pathway by disrupting HIF-1α interaction with p300. Na YR, Han KC, Park H, et al. Biochem. Biophys. Res. Commun. 434(4), 879-84, (2013)

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Differences in gene expression profiles in dermal fibroblasts from control and patients with age-related macular degeneration elicited by oxidative injury. Strunnikova N, Hilmer S, Flippin J, et al. Free Radic. Biol. Med. 39(6), 781-96, (2005)

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MicroRNAs differentially regulate carbonyl reductase 1 (CBR1) gene expression dependent on the allele status of the common polymorphic variant rs9024. Kalabus JL, Cheng Q, and Blanco JG PLoS ONE 7(11), e48622, (2012)

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Vitamins K interact with N-terminus α-synuclein and modulate the protein fibrillization in vitro. Exploring the interaction between quinones and α-synuclein. da Silva FL, Coelho Cerqueira E, de Freitas MS, et al. Neurochem. Int. 62(1), 103-12, (2013)

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5-Substituted [1]pyrindine derivatives with antiproliferative activity. Stéphanie Kolb et al Eur. J. Med. Chem. 45, 896-901, (2010)

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Superoxide dismutases and glutaredoxins have a distinct role in the response of Candida albicans to oxidative stress generated by the chemical compounds menadione and diamide. Chaves GM and da Silva WP Mem. Inst. Oswaldo Cruz 107(8), 998-1005, (2012)

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Antimutagenic and antioxidant properties of plumbagin and other naphthoquinones. Kumar S, Gautam S, and Sharma A Mutat. Res. 755(1), 30-41, (2013)

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In silico and in vitro characterization of anti-amyloidogenic activity of vitamin K3 analogues for Alzheimer's disease. Huy PD, Yu YC, Ngo ST, et al. Biochim. Biophys. Acta 1830(4), 2960-9, (2013)

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Species differences in response to photohemolytic agents. Robertson DG, Bailey DL, and Martin RA Photochem. Photobiol. 53(4), 455-61, (1991)

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ompW is cooperatively upregulated by MarA and SoxS in response to menadione. Collao B, Morales EH, Gil F, et al. Microbiology 159(Pt 4), 715-25, (2013)

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Novel insights into the antiproliferative effects and synergism of quercetin and menadione in human leukemia Jurkat T cells. Baran I, Ionescu D, Filippi A, et al. Leuk. Res. 38(7), 836-49, (2014)

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Vitamin K4 induces tumor cytotoxicity in human prostate carcinoma PC-3 cells via the mitochondria-related apoptotic pathway. Jiang Y, Yang J, Yang C, et al. Pharmazie 68(6), 442-8, (2013)

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Serum markers variation consistent with autoschizis induced by ascorbic acid-menadione in patients with prostate cancer. Lasalvia-Prisco E, Cucchi S, Vázquez J, et al. Med. Oncol. 20(1), 45-52, (2003)

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Menadione. Hassan GS Profiles Drug Subst. Excip. Relat. Methodol. 38, 227-313, (2013)

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The phosphatase inhibitor menadione (Vitamin K3) protects cells from EGFR inhibition by erlotinib and cetuximab. Perez-Soler R, Zou Y, et al. Clin. Cancer Res. 17(21), 6766-77, (2011)

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Inhibitory effects of vitamin K3 derivatives on DNA polymerase and inflammatory activity. Aoganghua A, Nishiumi S, et al. Int. J. Mol. Med. 28(6), 937-45, (2011)

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On methods for the detection of reactive oxygen species generation by human spermatozoa: analysis of the cellular responses to catechol oestrogen, lipid aldehyde, menadione and arachidonic acid. Aitken RJ, Smith TB, Lord T, et al. Andrology, (2013)

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Merck 14,5831

Beil. 7,IV,2430

Corp MSDS 1 (2), 2385:D / FT-IR 1 (2), 79:C / FT-IR 2 (2), 2484:C / IR-Spectra (3), 896:H / IR-Spectra (2), 784:E / NMR-Reference 2 (2), 85:B / RegBook 1 (2), 1683:H / Sax 6, 1882 / Sigma FT-IR 1 (2), 699:B / Structure Index 1, 267:B:1

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