Genomes and Genes
vitamin k 3
Summary: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.
- Wallace M, Bailey S, Fukuto J, Valentine J, Gralla E. Induction of phenotypes resembling CuZn-superoxide dismutase deletion in wild-type yeast cells: an in vivo assay for the role of superoxide in the toxicity of redox-cycling compounds. Chem Res Toxicol. 2005;18:1279-86 pubmed..Using this method, we analyzed the Parkinsonism-inducing compound 1-methyl-4-phenylpyridinium and found that redox cycling and superoxide toxicity are not the predominant factor in its toxic mechanism. ..
- Baumgartner H, Gerasimenko J, Thorne C, Ashurst L, Barrow S, Chvanov M, et al. Caspase-8-mediated apoptosis induced by oxidative stress is independent of the intrinsic pathway and dependent on cathepsins. Am J Physiol Gastrointest Liver Physiol. 2007;293:G296-307 pubmed
- Eggler A, Liu G, Pezzuto J, van Breemen R, Mesecar A. Modifying specific cysteines of the electrophile-sensing human Keap1 protein is insufficient to disrupt binding to the Nrf2 domain Neh2. Proc Natl Acad Sci U S A. 2005;102:10070-5 pubmed..Based on these results, a model is proposed that should aid in the understanding of Keap1-Nrf2 signaling mechanisms. ..
- Verrax J, Delvaux M, Beghein N, Taper H, Gallez B, Buc Calderon P. Enhancement of quinone redox cycling by ascorbate induces a caspase-3 independent cell death in human leukaemia cells. An in vitro comparative study. Free Radic Res. 2005;39:649-57 pubmed..In conclusion, our results indicate that the cytotoxicity of the association quinone/ascorbate on K562 cancer cells may be predicted on the basis of half-redox potentials of quinones. ..
- Acharya B, Choudhury D, Das A, Chakrabarti G. Vitamin K3 disrupts the microtubule networks by binding to tubulin: a novel mechanism of its antiproliferative activity. Biochemistry. 2009;48:6963-74 pubmed publisher..The obtained data suggested that menadione binds at the colchicine binding site to tubulin. Thus, we can conclude one novel mechanism of inhibition of cancer cell proliferation by menadione is through tubulin binding. ..
- Conde de la Rosa L, Schoemaker M, Vrenken T, Buist Homan M, Havinga R, Jansen P, et al. Superoxide anions and hydrogen peroxide induce hepatocyte death by different mechanisms: involvement of JNK and ERK MAP kinases. J Hepatol. 2006;44:918-29 pubmed..In normal hepatocytes, superoxide anions-induced caspase activation and apoptosis is dependent on JNK activity and totally abolished by superoxide scavengers. ..
- Ogawa M, Nakai S, Deguchi A, Nonomura T, Masaki T, Uchida N, et al. Vitamins K2, K3 and K5 exert antitumor effects on established colorectal cancer in mice by inducing apoptotic death of tumor cells. Int J Oncol. 2007;31:323-31 pubmed
- Mailloux R, Beriault R, Lemire J, Singh R, Chénier D, Hamel R, et al. The tricarboxylic acid cycle, an ancient metabolic network with a novel twist. PLoS ONE. 2007;2:e690 pubmed..These findings uncover an intricate link between TCA cycle and ROS homeostasis and may help explain the ineffective TCA cycle that characterizes various pathological conditions and ageing. ..
- Circu M, Rodriguez C, Maloney R, Moyer M, Aw T. Contribution of mitochondrial GSH transport to matrix GSH status and colonic epithelial cell apoptosis. Free Radic Biol Med. 2008;44:768-78 pubmed publisher..These results support the importance of mitochondrial GSH transport and the mtGSH status in oxidative cell killing. ..
- Matzno S, Yamaguchi Y, Akiyoshi T, Nakabayashi T, Matsuyama K. An attempt to evaluate the effect of vitamin K3 using as an enhancer of anticancer agents. Biol Pharm Bull. 2008;31:1270-3 pubmed..These findings suggest that VK3 induces G2/M arrest by inhibition of cyclin B/cdk1 complex formation, and is thus useful as an enhancer of G2 phase-dependent drugs in hepatic cancer chemotherapy. ..
- Gilloteaux J, Jamison J, Neal D, Summers J. Cell death by autoschizis in TRAMP prostate carcinoma cells as a result of treatment by ascorbate: menadione combination. Ultrastruct Pathol. 2005;29:221-35 pubmed..The organelle-free self-excisions caused an extreme reduction in cell size as well as chromatolysis and karyolysis that were consistent with cell death by autoschizis, but not with apoptosis. ..
- von Eiff C, McNamara P, Becker K, Bates D, Lei X, Ziman M, et al. Phenotype microarray profiling of Staphylococcus aureus menD and hemB mutants with the small-colony-variant phenotype. J Bacteriol. 2006;188:687-93 pubmed..Key results of the PM analysis were confirmed in independent growth studies and by using Etest strips for susceptibility testing. PM technology is a new and efficient technology for assessing cellular phenotypes in S. aureus. ..
- Pocsi I, Miskei M, Karanyi Z, Emri T, Ayoubi P, Pusztahelyi T, et al. Comparison of gene expression signatures of diamide, H2O2 and menadione exposed Aspergillus nidulans cultures--linking genome-wide transcriptional changes to cellular physiology. BMC Genomics. 2005;6:182 pubmed
- Lannergård J, von Eiff C, Sander G, Cordes T, Seggewiss J, Peters G, et al. Identification of the genetic basis for clinical menadione-auxotrophic small-colony variant isolates of Staphylococcus aureus. Antimicrob Agents Chemother. 2008;52:4017-22 pubmed publisher..These data show that mutations in menB cause the SCV phenotype in these clinical isolates. This is the first report on the genetic basis of menadione-auxotrophic SCVs determined in clinical S. aureus isolates. ..
- Castro F, Mariani D, Panek A, Eleutherio E, Pereira M. Cytotoxicity mechanism of two naphthoquinones (menadione and plumbagin) in Saccharomyces cerevisiae. PLoS ONE. 2008;3:e3999 pubmed publisher..In addition, the Gtt2 isoform seemed to act as a general protective factor involved in quinone detoxification. ..
- Hegde K, Varma S. Combination of glycemic and oxidative stress in lens: implications in augmentation of cataract formation in diabetes. Free Radic Res. 2005;39:513-7 pubmed..Similarly, the galactosemic lenses were also more susceptible to menadione dependent decrease in ATP and GSH. ..
- Gu M, Imlay J. The SoxRS response of Escherichia coli is directly activated by redox-cycling drugs rather than by superoxide. Mol Microbiol. 2011;79:1136-50 pubmed publisher..Under these conditions SoxRS induction was protective. Thus it is physiologically appropriate that the SoxR protein directly senses redox-cycling drugs rather than superoxide. ..
- Beck R, Pedrosa R, Dejeans N, Glorieux C, Leveque P, Gallez B, et al. Ascorbate/menadione-induced oxidative stress kills cancer cells that express normal or mutated forms of the oncogenic protein Bcr-Abl. An in vitro and in vivo mechanistic study. Invest New Drugs. 2011;29:891-900 pubmed publisher..The mechanism underlying this cytotoxicity involves the oxidative cleavage of Hsp90 with a subsequent loss of its chaperone function thus leading to degradation of wild-type and mutated Bcr-Abl protein. ..
- Baumgartner H, Gerasimenko J, Thorne C, Ferdek P, Pozzan T, Tepikin A, et al. Calcium elevation in mitochondria is the main Ca2+ requirement for mitochondrial permeability transition pore (mPTP) opening. J Biol Chem. 2009;284:20796-803 pubmed publisher..We conclude that elevated Ca2+ in mitochondria is the crucial factor in determining whether cells undergo oxidative stress-induced apoptosis. ..
- Kassouf W, Highshaw R, Nelkin G, Dinney C, Kamat A. Vitamins C and K3 sensitize human urothelial tumors to gemcitabine. J Urol. 2006;176:1642-7 pubmed..3 mm3 daily) (p < 0.05). Vitamins C and K3 have significant antiproliferative and apoptotic effects when used in combination. This combination enhances the efficacy of gemcitabine against bladder cancer in vivo. ..
- Loor G, Kondapalli J, Schriewer J, Chandel N, Vanden Hoek T, Schumacker P. Menadione triggers cell death through ROS-dependent mechanisms involving PARP activation without requiring apoptosis. Free Radic Biol Med. 2010;49:1925-36 pubmed publisher..These studies suggest that multiple redundant cell death pathways are activated by menadione, but that PARP plays an essential role in mediating each of them. ..
- Beck R, Verrax J, Dejeans N, Taper H, Calderon P. Menadione reduction by pharmacological doses of ascorbate induces an oxidative stress that kills breast cancer cells. Int J Toxicol. 2009;28:33-42 pubmed publisher..This differential sensitivity may have clinical applications. ..
- Chen D, Wilkinson C, Watt S, Penkett C, Toone W, Jones N, et al. Multiple pathways differentially regulate global oxidative stress responses in fission yeast. Mol Biol Cell. 2008;19:308-17 pubmed..These data reveal a considerable plasticity and differential control of regulatory pathways in distinct oxidative stress conditions, providing both specificity and backup for protection from oxidative damage. ..
- Shneyvays V, Leshem D, Shmist Y, Zinman T, Shainberg A. Effects of menadione and its derivative on cultured cardiomyocytes with mitochondrial disorders. J Mol Cell Cardiol. 2005;39:149-58 pubmed
- Azevedo D, Tacnet F, Delaunay A, Rodrigues Pousada C, Toledano M. Two redox centers within Yap1 for H2O2 and thiol-reactive chemicals signaling. Free Radic Biol Med. 2003;35:889-900 pubmed..These data indicate that yeast cells cannot sense these compounds through the same molecular devices, albeit they are all electrophilic. ..
- Chauhan N, Inglis D, Roman E, Pla J, Li D, Calera J, et al. Candida albicans response regulator gene SSK1 regulates a subset of genes whose functions are associated with cell wall biosynthesis and adaptation to oxidative stress. Eukaryot Cell. 2003;2:1018-24 pubmed..Further, SSK1 appears to have a regulatory function in some aspects of cell wall biosynthesis. Thus, the functions of C. albicans SSK1 differ from those of S. cerevisiae SSK1. ..
- Lamson D, Plaza S. The anticancer effects of vitamin K. Altern Med Rev. 2003;8:303-18 pubmed..Tyrosine kinases associated with cyclins have also been shown to be affected by vitamin K, which can lead to cell cycle arrest and cell death. ..
- Verrax J, Cadrobbi J, Delvaux M, Jamison J, Gilloteaux J, Summers J, et al. The association of vitamins C and K3 kills cancer cells mainly by autoschizis, a novel form of cell death. Basis for their potential use as coadjuvants in anticancer therapy. Eur J Med Chem. 2003;38:451-7 pubmed..The aim is to prepare the introduction of the association of vitamins C and K(3) into human clinics as a new, non-toxic adjuvant cancer therapy. ..
- Bates D, von Eiff C, McNamara P, Peters G, Yeaman M, Bayer A, et al. Staphylococcus aureus menD and hemB mutants are as infective as the parent strains, but the menadione biosynthetic mutant persists within the kidney. J Infect Dis. 2003;187:1654-61 pubmed
- Jamison J, Gilloteaux J, Nassiri M, Venugopal M, Neal D, Summers J. Cell cycle arrest and autoschizis in a human bladder carcinoma cell line following Vitamin C and Vitamin K3 treatment. Biochem Pharmacol. 2004;67:337-51 pubmed..These results suggest that Ca(2+) disregulation activates at least one DNase which degrades tumor cell DNA and induces tumor cell death. ..
- Verrax J, Cadrobbi J, Marques C, Taper H, Habraken Y, Piette J, et al. Ascorbate potentiates the cytotoxicity of menadione leading to an oxidative stress that kills cancer cells by a non-apoptotic caspase-3 independent form of cell death. Apoptosis. 2004;9:223-33 pubmed
- Osorio H, Carvalho E, Del Valle M, Günther Sillero M, Moradas Ferreira P, Sillero A. H2O2, but not menadione, provokes a decrease in the ATP and an increase in the inosine levels in Saccharomyces cerevisiae. An experimental and theoretical approach. Eur J Biochem. 2003;270:1578-89 pubmed..The strong decrease in the ATP level upon H2O2 treatment is an important factor to be considered for understanding the response of yeast, and probably other cell types, to oxidative stress. ..
- Hwang C, Rhie G, Oh J, Huh W, Yim H, Kang S. Copper- and zinc-containing superoxide dismutase (Cu/ZnSOD) is required for the protection of Candida albicans against oxidative stresses and the expression of its full virulence. Microbiology. 2002;148:3705-13 pubmed..Thus, these results suggest that Cu/ZnSOD is required for the protection of C. albicans against oxidative stresses and for the full virulence of the organism to be expressed. ..
- Laux I, Nel A. Evidence that oxidative stress-induced apoptosis by menadione involves Fas-dependent and Fas-independent pathways. Clin Immunol. 2001;101:335-44 pubmed..In addition, the mitochondrial changes coincided with ATP depletion. The failure in ATP production explains the occurrence of Fas-independent death events. ..
- Shapira M, Segal E, Botstein D. Disruption of yeast forkhead-associated cell cycle transcription by oxidative stress. Mol Biol Cell. 2004;15:5659-69 pubmed..The apparent involvement of a forkhead protein in HP-induced cell cycle arrest, similar to that reported for Caenorhabditis elegans and human, describes a potentially novel stress response pathway in yeast. ..
- Gilloteaux J, Jamison J, Arnold D, Taper H, Summers J. Ultrastructural aspects of autoschizis: a new cancer cell death induced by the synergistic action of ascorbate/menadione on human bladder carcinoma cells. Ultrastruct Pathol. 2001;25:183-92 pubmed..1998; 20: 564-575). This morphological characterization of autoschizic cell death confirms and extends the authors previous reports and demonstrates that this cell death is distinct from apoptosis. ..
- Oztopçu P, Kabadere S, Mercangoz A, Uyar R. Comparison of vitamins K1, K2 and K3 effects on growth of rat glioma and human glioblastoma multiforme cells in vitro. Acta Neurol Belg. 2004;104:106-10 pubmed..We concluded that vitamin K3 is more effective than vitamin K2 for inhibition of cancer cell growth, and might have an alternative value as an anticancer drug against glioblastoma multiforme. ..
- Taper H, Jamison J, Gilloteaux J, Summers J, Calderon P. Inhibition of the development of metastases by dietary vitamin C:K3 combination. Life Sci. 2004;75:955-67 pubmed..These results demonstrate that oral vitamin C and K(3) significantly inhibited the metastases of T.L.T. tumors in C3H mice. At least a portion of this inhibition was due to tumor cell death by autoschizis. ..
- Gilloteaux J, Jamison J, Lorimer H, Jarjoura D, Taper H, Calderon P, et al. Autoschizis: a new form of cell death for human ovarian carcinoma cells following ascorbate:menadione treatment. Nuclear and DNA degradation. Tissue Cell. 2004;36:197-209 pubmed..Histochem. Cytochem. 49 (2001) 109] which demonstrated that the VC:VK3 combination induced autoschizic cell death by a series of cytoplasmic excisions without organelles along with specific nuclear ultrastructural damage. ..
- Briere J, Schlemmer D, Chretien D, Rustin P. Quinone analogues regulate mitochondrial substrate competitive oxidation. Biochem Biophys Res Commun. 2004;316:1138-42 pubmed..As a result, idebenone strongly favoured succinate over NADH oxidation. This study therefore suggests that any therapeutic use of quinone analogues should take into account their specific effect on each respiratory chain dehydrogenase. ..
- De Marchi U, Pietrangeli P, Marcocci L, Mondovi B, Toninello A. L-Deprenyl as an inhibitor of menadione-induced permeability transition in liver mitochondria. Biochem Pharmacol. 2003;66:1749-54 pubmed
- Lasalvia Prisco E, Cucchi S, Vazquez J, Lasalvia Galante E, Golomar W, Gordon W. Serum markers variation consistent with autoschizis induced by ascorbic acid-menadione in patients with prostate cancer. Med Oncol. 2003;20:45-52 pubmed..Ascorbic acid-menadione could be emerging as a new antitumoral chemotherapy. ..
- Gerasimenko J, Gerasimenko O, Palejwala A, Tepikin A, Petersen O, Watson A. Menadione-induced apoptosis: roles of cytosolic Ca(2+) elevations and the mitochondrial permeability transition pore. J Cell Sci. 2002;115:485-97 pubmed..These results suggest a twin-track model in which both intracellular release of Ca(2+) and induction of the permeability transition pore are required for initiation of apoptosis. ..
- Okayasu H, Ishihara M, Satoh K, Sakagami H. Cytotoxic activity of vitamins K1, K2 and K3 against human oral tumor cell lines. Anticancer Res. 2001;21:2387-92 pubmed
- Gilloteaux J, Jamison J, Arnold D, Ervin E, Eckroat L, Docherty J, et al. Cancer cell necrosis by autoschizis: synergism of antitumor activity of vitamin C: vitamin K3 on human bladder carcinoma T24 cells. Scanning. 1998;20:564-75 pubmed..This process of cell death induced by oxidative stress was named autoschizis because it showed both apoptotic and necrotic morphologic characteristics. ..
- Simamura E, Shimada H, Ishigaki Y, Hatta T, Higashi N, Hirai K. Bioreductive activation of quinone antitumor drugs by mitochondrial voltage-dependent anion channel 1. Anat Sci Int. 2008;83:261-6 pubmed publisher..In the quinone antitumor drugs, menadione (VK3), adriamycin and mitomycin C, mitochondrial VDAC1 bioreductively activated VK3. These results demonstrate that mitochondrial VDAC1 is a pharmacologic target for the treatment of tumor. ..
- Singh R, Czaja M. Compensatory mechanisms and the type of injury determine the fate of cells with impaired macroautophagy. Autophagy. 2008;4:516-8 pubmed..These findings demonstrate that the effects of a loss of macroautophagy on the cellular death response differ depending on the mechanism of cellular injury and the compensatory changes in other forms of autophagy. ..
- Lanfranchi D, Belorgey D, Müller T, Vezin H, Lanzer M, Davioud Charvet E. Exploring the trifluoromenadione core as a template to design antimalarial redox-active agents interacting with glutathione reductase. Org Biomol Chem. 2012;10:4795-806 pubmed publisher..The resulting trifluoromethyl derivative 5 showed a potent antimalarial activity per se against malarial parasites in culture. ..
- Kasemets K, Suppi S, Künnis Beres K, Kahru A. Toxicity of CuO nanoparticles to yeast Saccharomyces cerevisiae BY4741 wild-type and its nine isogenic single-gene deletion mutants. Chem Res Toxicol. 2013;26:356-67 pubmed publisher..Lastly, as yeast retained its viability in DI even by 24th hour of incubation, the profiling of the acute basal toxicity of chemicals toward yeasts may be conducted in DI. ..
- Guthrie H, Welch G. Determination of high mitochondrial membrane potential in spermatozoa loaded with the mitochondrial probe 5,5',6,6'-tetrachloro-1,1',3,3'-tetraethylbenzimidazolyl-carbocyanine iodide (JC-1) by using fluorescence-activated flow cytometry. Methods Mol Biol. 2008;477:89-97 pubmed publisher..We found that the reactive oxygen species generator, menadione reduced sperm motility and reduced Deltapsi(m) in a dose responsive fashion that was closely correlated with the loss of motility. ..
- Shah M, Stebbins J, Dewing A, Qi J, Pellecchia M, Ronai Z. Inhibition of Siah2 ubiquitin ligase by vitamin K3 (menadione) attenuates hypoxia and MAPK signaling and blocks melanoma tumorigenesis. Pigment Cell Melanoma Res. 2009;22:799-808 pubmed publisher..These findings reveal an efficient platform for the identification of Siah inhibitors while identifying and characterizing MEN as Siah inhibitor that attenuates hypoxia and MAPK signaling, and inhibits melanoma tumorigenesis. ..