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M5750 Sigma

Menadione sodium bisulfite

≥95% (TLC)

Synonym: 2-Methyl-1,4-naphthoquinone sodium bisulfite

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Description

Other Notes

Water soluble vitamin K3.

Biochem/physiol Actions

Menadione sodium bisulfite is a water-soluble form of menadione, which belongs to the Vitamin K class of compounds. These are necessary for the biosynthesis of prothrombin and other blood clotting factors. Menadione is a prothrombogenic compound and is used as a model quinone in cell culture and in vivo investigations.

Menadione has been shown to affect gap-junctional intercellular communication by mediation of tyrosine phosphorylation. Menadione has demonstrated cytotoxic activity against a variety of cell lines and can induce apoptosis in cultured cells, such as osteoclasts and osteoblasts, via elevation of peroxide and superoxide radical levels.

An HPLC method for detection of menadione sodium bisulfite in multivitamin formulations has been published. A chemiluminescence assay for menadione sodium bisulfite in pharmaceutical preparations and biological fluids has been reported.

Features and Benefits

This compound was developed by Eli Lilly. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Risk Statements (Europe) 
Safety Statements (Europe) 
24/25-60-61
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

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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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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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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Determination of menadione sodium hydrogen sulphite and nicotinamide in multivitamin formulations by high-performance liquid chromatography Sadlej-Sosnowska, N., et al. J. Chromatogr. A 1st ed., 357, 227-232, (1986)

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

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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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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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[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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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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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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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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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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Farnesol Misplaces Tip-localized Rho Proteins And Inhibits Cell Wall Integrity Signalling In Aspergillus Fumigatus. Dichtl, K., et al. Mol. Microbiol. 76, 1191-204, (2010)

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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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2-Methyl-1,4-naphthoquinone, vitamin K3, decreases gap-junctional intercellular communication via activation of the epidermal growth factor receptor/extracellular signal-regulated kinase cascade Klotz, L.O., et al. Cancer Res. 17th ed., 62, 4922-4928, (2002)

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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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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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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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Cytotoxic activity of vitamins K1, K2 and K3 against human oral tumor cell lines Okayasu, H. et al. Anticancer Res. 4Ath ed., 21, 2387-2392, (2001)

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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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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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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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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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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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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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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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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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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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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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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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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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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

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