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Research Article

Evaluation of N-acetyl-S-(p-chlorophenylcarbamoyl)cysteine as an irreversible inhibitor of mammalian thioredoxin reductase1

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Pages 229-235 | Received 10 Nov 2014, Accepted 13 Jan 2015, Published online: 17 Mar 2015

References

  • Xiao GQ, Liang BX, Chen SH, et al. 3-Nitro-2H-chromenes as a new class of inhibitors against thioredoxin reductase and proliferation of cancer cells. Arch Pharm (Weinheim) 2012;345:767–70
  • Liu Y, Li Y, Yu S, Zhao G. Recent advances in the development of thioredoxin reductase inhibitors as anticancer agents. Curr Drug Targets 2012;13:1432–44
  • Navakoski de Oliveira K, Andermark V, von Grafenstein S, et al. Butyltin(IV) benzoates: inhibition of thioredoxin reductase, tumor cell growth inhibition, and interactions with proteins. ChemMedChem 2013;8:256–64
  • Xu J, Arner ES. Pyrroloquinoline quinone modulates the kinetic parameters of the mammalian selenoprotein thioredoxin reductase 1 and is an inhibitor of glutathione reductase. Biochem Pharmacol 2012;83:815–20
  • Wang L, Yang Z, Fu J, et al. Ethaselen: a potent mammalian thioredoxin reductase 1 inhibitor and novel organoselenium anticancer agent. Free Radic Biol Med 2012;52:898–908
  • Arner ES. Focus on mammalian thioredoxin reductases – important selenoproteins with versatile functions. Biochim Biophys Acta 2009;1790:495–526
  • Cai W, Zhang B, Duan D, et al. Curcumin targeting the thioredoxin system elevates oxidative stress in HeLa cells. Toxicol Appl Pharmacol 2012;262:341–8
  • Yoon BI, Kim DY, Jang JJ, Han JH. Altered expression of thioredoxin reductase-1 in dysplastic bile ducts and cholangiocarcinoma in a hamster model. J Vet Sci 2006;7:211–16
  • Berggren M, Gallegos A, Gasdaska JR, et al. Thioredoxin and thioredoxin reductase gene expression in human tumors and cell lines, and the effects of serum stimulation and hypoxia. Anticancer Res 1996;16:3459–66
  • He J, Li D, Xiong K, et al. Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: organoselenium compounds for cancer therapy. Bioorg Med Chem 2012;20:3816–27
  • Fang J, Lu J, Holmgren A. Thioredoxin reductase is irreversibly modified by curcumin: a novel molecular mechanism for its anticancer activity. J Biol Chem 2005;280:25284–90
  • Grogan TM, Fenoglio-Prieser C, Zeheb R, et al. Thioredoxin, a putative oncogene product, is overexpressed in gastric carcinoma and associated with increased proliferation and increased cell survival. Human Pathol 2000;31:475–81
  • Smart DK, Ortiz KL, Mattson D, et al. Thioredoxin reductase as a potential molecular target for anticancer agents that induce oxidative stress. Cancer Res 2004;64:6716–24
  • Yoo MH, Xu XM, Carlson BA, et al. Thioredoxin reductase 1 deficiency reverses tumor phenotype and tumorigenicity of lung carcinoma cells. J Biol Chem 2006;281:13005–8
  • Yoo MH, Xu XM, Carlson BA, et al. Targeting thioredoxin reductase 1 reduction in cancer cells inhibits self-sufficient growth and DNA replication. PLoS One 2007;2:e1112
  • Chen W, Seefeldt T, Young A, et al. Design, synthesis, and biological evaluation of N-acetyl-S-(p-chlorophenylcarbamoyl)cysteine and its analogs as a novel class of anticancer agents. Bioorg Med Chem 2011;19:287–94
  • Hashemy SI, Ungerstedt JS, Zahedi Avval F, Holmgren A. Motexafin gadolinium, a tumor-selective drug targeting thioredoxin reductase and ribonucleotide reductase. J Biol Chem 2006;281:10691–7
  • Mura P, Camalli M, Bindoli A, et al. Activity of rat cytosolic thioredoxin reductase is strongly decreased by trans-[bis(2-amino-5- methylthiazole)tetrachlororuthenate(III)]: first report of relevant thioredoxin reductase inhibition for a ruthenium compound. J Med Chem 2007;50:5871–4
  • Casini A, Gabbiani C, Sorrentino F, et al. Emerging protein targets for anticancer metallodrugs: inhibition of thioredoxin reductase and cathepsin B by antitumor ruthenium(II)-arene compounds. J Med Chem 2008;51:6773–81
  • Arner ES, Holmgren A. Measurement of thioredoxin and thioredoxin reductase. Current protocols in toxicology/editorial board, Mahin D Maines. 2001; chapter 7:Unit 7 4
  • Kitz R, Wilson IB. Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase. J Biol Chem 1962;237:3245–9
  • Rice KP, Klinkerch EJ, Gerber SA, et al. Thioredoxin reductase is inhibited by the carbamoylating activity of the anticancer sulfonylhydrazine drug laromustine. Mol Cell Biochem 2012;370:199–207
  • Chew EH, Lu J, Bradshaw TD, Holmgren A. Thioredoxin reductase inhibition by antitumor quinols: a quinol pharmacophore effect correlating to antiproliferative activity. FASEB J 2008;22:2072–83
  • Fujiwara N, Fujii T, Fujii J, Taniguchi N. Roles of N-terminal active cysteines and C-terminal cysteine-selenocysteine in the catalytic mechanism of mammalian thioredoxin reductase. J Biochem 2001;129:803–12
  • Cai W, Zhang L, Song Y, et al. Small molecule inhibitors of mammalian thioredoxin reductase. Free Radic Biol Med 2012;52:257–65
  • Wessjohann LA, Schneider A, Abbas M, Brandt W. Selenium in chemistry and biochemistry in comparison to sulfur. Biol Chem 2007;388:997–1006

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