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Review

Agents that target cysteine residues of biomolecules and their therapeutic potential

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Pages 765-787 | Published online: 25 Feb 2005

Bibliography

  • WOYCECHOWSKY KJ, RAINES RT: Native disulfide bond formation in proteins. CUIT. Opin. Chem. Biol. (2000) 4:533–539.
  • WEDEMEYER WJ, WELKER E, NARAYAN M, SCHERAGA HA: Disulfide bonds and protein folding. Biochemistry (2000) 39:4207–4216.
  • CRAVATT BF, SORENSEN EJ: Chemical strategies for the global analysis of protein function. Curr. Opin. Chem. Biol. (2000) 4:663–668.
  • WILLIAMS DLH: The chemistry of S-nitrosothiols. Acc. Chem Res. (1999) 32:869–876.
  • VINER RI, WILLIAMS TD, SCHONEICH C: Peroxynitrite modification of protein thiols: oxidation, nitrosyla-tion and S-glutathiolation of functionally important cysteine residue(s) in the sarcoplasmic reticulum of Ca-ATP-ase. Biochemistry (1999) 38:12408–12415.
  • VALLEE B, MARET W: Metallothionein III. In: Metallothioneins. Suzuki KT, Imura N, Kimura M (Eds.), Birkhauser, Basel, Switzerland (1993):1–28.
  • BERTINI I, BRIGANTI F, SCOZZAFAVA A: Zinc proteins. In: Handbook of Metal-Ligand Interactions of Biological Fluids. Bertini I (Ed.), VCH, Weinhaim, Germany (1995) :175–191.
  • MOCCHEGIANI E, MUZZIOLI M, GIACCONI R: Zinc and immunoresistance to infection in aging: new biological tools. Trends Pharm. Sci. (2000) 21:205–208.
  • MOCCHEGIANI E, MUZZIOLI M, CIPRIANO C, GIACCONI R: Zinc, T-cell pathways, aging: the role of metallothioneins. Mech. Ageing Dev. (1998) 106:183–204.
  • MOCCHEGIANI E, GIACCONI R, MUZZIOLI M, CIPRIANO C: Zinc, infections and immunosenescence. Mech. Ageing Dev. (2000) 121:21–35.
  • VALEE BL, AULD DS: Zinc coordination, function and structure of zinc enzymes and other proteins. Biochem-istry (1990) 29:5647–5659.
  • •A classical mini-review on zinc enzymes.
  • SUPURAN CT, SCOZZAFAVA A: Carbonic anhydrase inhibitors and their therapeutic potential. Exp. Opin. Ther. Patents (2000) 10:575–600.
  • ••An exhaustive review on the CA inhibitors.
  • SUPURAN CT, SCOZZAFAVA A, MASTROLORENZO A: Bacterial proteases: current therapeutic use and future prospects for the development of new antibiotics. Exp. Opin. Ther. Patents (2001) 11:221–259.
  • ••An exhaustive review on bacterial proteases and theirpotential for the development of new generation antibiotics.
  • SCHAFER SC, DAWES RLF, ELSENHANS B, FORTH W, SCCIMANN K: Metals. In: Toxicology. Marquardt H, Schafer SC, McClellan RD, Welsch F (Eds.), Academic Press (1999):755–804.
  • BOUHOUCHE N, SYVANEN M, KADO CI: The origin of prokaryotic C2H2 zinc finger regulators. Trends Microbiol. (2000) 8 :77–81.
  • COX EH, MCLENDON GL: Zinc-dependent protein folding. Curr. Opin. Chem. Bid (2000) 4:162–165.
  • BUOLAMWINI JK: Novel anticancer drug discovery. Curr. Opin. Chem. Biol. (1999) 3:500–509.
  • OTTO HH, SCHIRMEISTER T: Cysteine proteases and their inhibitors. Chem. Rev. (1997) 97:133–171.
  • ••An excellent review of this family of enzymes and of theirmain types of inhibitors.
  • VELLA S, PALMISANO L: Antiretroviral therapy: state of the HAART. Antiviral Res. (2000) 45:1–7.
  • JOLY V, YENY P: New trends in antiretroviral therapy of HIV infection. Eur.J. Int. Med. (2000) 11:301–308.
  • KAUFMANN GR, COOPER DA: Antiretroviral therapy of HIV-1 infection: established treatment strategies and new therapeutic options. Curr. Opin. Microbiol (2000) 3:508–514.
  • RICE WG, SCHAEFFER CA, HARTEN B et al: Inhibition of HIV infectivity by zinc-ejecting C-nitroso compounds. Nature (1993) 361:473–475.
  • RICE WG, SUPKO JG, MALSPEIS L et al.: Inhibitors of HIV nucleocapsid protein zinc fingers as candidates for the treatment of AIDS. Science (1995) 270:1194–1197.
  • ••A revolutionary paper on the application of zinc extrusionfrom viral zinc finger proteins, as a novel therapeutic approach for HIV infection.
  • MELY Y, CORNILLE F, FOURNIE-ZALUSKI MC, DARLIX JL, ROQUES BP, GERARD D: Investigation of zinc-binding affinities of Moloney murine leukemia virus nucleo-capsid protein and related zinc finger and modified peptides. Biopolymers (1991) 31:899–906.
  • RAMBOARINA S, MORELLER N, FOURNIE-ZALUSKI MC, ROQUES BP: Structural investigation on the require-ment of CCHFIzinc finger type nucleocapsid protein of human immunodeficiency virus 1. Biochemistry (1999) 38:9600–9607.
  • LOO JA, HOLLER TP, SANCHEZ J, GOGLIOTTI R, MALONEY L, REILY MD: Biophysical characterization of zinc ejection from HIV nucleocapsid protein by anti-HIV 2,2t-dithiobis[benzamides] and benzisothia-zolones. J. Med. Chem. (1996) 39:4313–4320.
  • DOMAGALA JM, BADER JP, GOGLIOTTI R et al.: A new class of anti-HIV agents targeted towards the nucleo-capsid protein NCp7: the 2,2t-dithiobisbenzamides. Bioorg. Med. Chem. (1997) 5:569–579.
  • HUANG M, MAYNARD A, TURPIN JA et al.: Anti-HIV agents that selectively target retroviral nucleocapsid protein zinc fingers without affecting cellular zinc fingers. J. Med. Chem. (1998) 41:1371–1381.
  • ••An excellent paper in which it is shown that zinc extrusionfrom viral zinc finger proteins does not interfere with cellular zinc fingers, validating thus this approach for the treatment of viral diseases.
  • TURPIN JA, SONG Y, INMAN JK et al.: Synthesis and biological properties of novel pyridinioalkanoyl thiolesters (PATE) as anti-HIV-1 agents that target the viral nucleocapsid protein zinc fingers. J. Med. Chem. (1999) 42:67–86.
  • BASRUR V, SONG Y, MAZUR SJ et al.: Inactivation of HIV-1 nucleocapsid protein P7 by pyridinioalkanoyl thiolesters. J. Biol. Chem. (2000) 275:14890–14897.
  • SCOZZAFAVA A, MENABUONI L, MINCIONE F, BRIGANTIF, MINCIONE G, SUPURAN CT: Carbonic anhydrase inhibitors: Perfluoroalkyl/aryl-substituted derivatives of aromatic/heterocyclic sulfonamides as topical intraocular pressure lowering agents with prolonged duration of action. J. Med. Chem. (2000) 43:4542–4551
  • CASINI A, SCOZZAFAVA A, MINCIONE F, MENABUONI L, ILIES MA, SUPURAN CT: Carbonic anhydrase inhibitors: water soluble 4-sulfamoylphenylthioureas as topical intraocular pressure lowering agents with long lasting effects. J. Med. Chem. (2000) 43:4884–4892.
  • FUJITA M., OTSUKA M, SUGIURA Y: Metal-chelating inhibitors of a zinc finger protein HIV-EP1 remarkable potentiation of inhibitory activity by introduction of SH groups. J. Med. Chem. (1996) 39:503–507.
  • ZUTSHI R, CHMIELEWSKI J: Targeting the dimerization interface for irreversible inhibition of HIV-1 protease. Bioorg. Med. Chem. Lett. (2000) 10:1901–1903.
  • WLODAWER A, GUSTCHINA A: Structural and biochemical studies of retroviral proteases. Biochim. Biophys. Acta (2000) 1477: 16–34.
  • ••An excellent paper on the HIV protease and its inhibitors,accounted for by one of the most prominent figures in this research field (AW).
  • FENOUILLET E, BARBOUCHE R, COURAGEOT J, MIQUELIS R: The catalytic activity of protein disulfide isomerase is involved in human immunodeficiency virus envelope-mediated membrane fusion after CD4 cell binding. J. Infect. Dis. (2001) 183:744–752.
  • ••This papers demonstrates the involvement of PDI in HIVentry within the cell and forms the basis for design of novel anti-HIV therapies based on PDI inhibitors.
  • FRATERNALE A, CASABIANCA A, TONELLI A, CHIARAN- TINT L, BRANDI G, MAGNANI M: New drug combination for the treatment of murine AIDS and macrophage protection. Eur.j Clin. Invest. (2001) 31:248–252.
  • ••A novel combination therapy highly effective in thetreatment of murine AIDS, which includes agents able to eradicate the virus from places difficult to access by the enzyme inhibitors used in conventional HAART.
  • AUBORN KJ, CARTER TH: Treatment of papillomavirus gynecologic infections. Clin. Lab. Med. (2000) 20:407–422.
  • MCGLENNEN RC: Human papillomavirus oncogenesis. Clin. Lab. Med. (2000) 20:383–406.
  • HARWOOD CA, SURENTHERAN T, MCGREGOR JM et al.: Human papillomavirus infection and non-melanoma skin cancer in immunosuppressed and immunocom-petent individuals. J Med. Virol. (2000) 61:289–297.
  • ISHIJI T, KAWASE M, HONDA M, NIIMURA M, YOSHIMURA E, MATSUKURA T: Distinctive distribution of human papillomavirus Type 16 and Type 20 in the tonsillar and the skin carcinomas of a patient with epidermodysplasia verruciformis. Br. J. Dermatol (2000) 143:1005–1010.
  • DAHL MV: Irniquimod: an immune response modifier. J. Am. Acad. Dermatol (2000) 43:51–55.
  • TONG X, HOWLEY PM: The bovine papillomavirus E6 oncoprotein interacts with paxillin and disrupts the actin cytoskeleton. Proc. Natl. Acad. Sci. USA (1997) 94:4412–4417.
  • KAO WH, BEAUDENON SL, TALIS AL, HUIBREGTSE JM, HOWLEY PM: Human papillomavirus Type 16 E6 induces self-ubiquitination of the E6AP ubiquitin-pr otein ligase. j Vim/. (2000) 74:6408–6417.
  • SASAGAWA T, MINEMOTO Y, BASHA W et al.: A new PCR-based assay amplifies the E6-E7 genes of most mucosal human papillomaviruses. Virus Res. (2000) 67:127–139.
  • GROSSMAN SR, LAIMINS LA: E6 protein of humanpapillomavirus Type 18 binds zinc. Oncogene (1989) 4:1089–1093.
  • BEERHEIDE W, BERNARD HU, TAN YJ, GANESAN A, RICEWG, TING AE: Potential drugs against cervical cancer: zinc-ejecting inhibitors of human papillomavirus Type 16 E6 oncoprotein. J Natl. Cancer Inst. (1999) 91:1211–1220.
  • BEERHEIDE W, SIM MM, TAN YJ, BERNARD HU, TING AE: Inactivation of the human papillomavirus-16 E6 oncoprotein by organic disulfides. Bioorg. Med. Chem. (2000) 8:2549–2560.
  • ••An excellent paper on compounds producing zinc ejectionfrom HPV zinc fingers, with the possibility to apply such derivatives as a new treatment of papilloma viruses.
  • BAUM EZ, DING WD, SIEGEL MM et al: Flavins inhibit human cytomegalovirus ULSO protease via disulfide bond formation. Biochemistry (1996) 35:5847–5855.
  • BAUM EZ, SIEGEL MM, BEBERNITZ GA et al: Inhibition of human cytomegalovirus ULSO protease by specific intramolecular disulfide bond formation. Biochemistry (1996) 35:5838–5846.
  • ERTL P, COOPER D, ALLEN G, SLATER MJ: 2-Chloro-3-substituted-1,4-naphthoquinone inactivators of human cytomegalovirus ULSO protease. Bioorg. Med. Chem. Lett. (1999) 9:2863–2866.
  • MEDINA JC, SHAN B, BECKMANN H et al: Novel antineo-plastic agents with efficacy against multidrug resistant tumor cells. Bioorg. Med. Chem. Lett. (1998) 8:2653–2656.
  • ••An excellent paper on the design of a new class of antitu-mour drugs, with a completely new mechanism of action.
  • MEDINA JC, ROCHE D, SHAN B et al.: Novel halogenated sulfonamides inhibit the growth of multidrug resistant MCF-7/ADR cancer cells. Bioorg. Med. Chem. Lett. (1999) 9:1843–1846.
  • SHAN B, MEDINA JC, SANTHA E et al.: Selective, covalent modification of I3-tubulin residue Cys-239 by 1138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc. Nati Acad. Sci. USA (1999) 96:5686–5691
  • SCOZZAFAVA A, MASTROLORENZO A, SUPURAN CT: Arylsulfonyl-N,N-diethyl-dithiocarbamates: a novel class of antitumor agents. Bioorg. Med. Chem. Lett. (2000) 10:1887–1891.
  • SCOZZAFAVA A, MASTROLORENZO A, SUPURAN CT: Arylsulfonyl-N,N-dialkyl-dithiocarbamates as tumor cell growth inhibitors: novel agents targeting 13-tubulin?./. Enz. Inhib. (2001) 16:In press.
  • SCOZZAFAVA A, SUPURAN CT: Carbonic anhydrase inhibitors: synthesis of N-morpholylthiocarbonyl sulfenylamino aromatic/heterocyclic sulfonamides and their interaction with isozymes I, II and W. Bioorg. Med. Chem. Lett. (2000) 10:1117–1120.
  • SUPURAN CT, BRIGANTI F, TILLI S, CHEGWIDDEN WR,SCOZZAFAVA A: Carbonic anhydrase inhibitors. Sulfonamides as antitumor agents? Bioorg. Med. Chem. (2001) 9:703–714.
  • WITTINGHOFER A, WALDMANN H: Ras - A molecular switch involved in tumor formation. Angew. Chem. Int. Ed (2000) 39:4192–4214.
  • ••An excellent, comprehensive review on the Ras protein.
  • COHEN LH, PIETERMAN E, VAN LEEUWEN REW et al:Inhibitors of prenylation of Ras and other G-proteins and their applications as therapeutics. Biochem. Pharmacol (2000) 60:1061–1068.
  • HILL BT, PERRIN D, KRUCZYNSKI A: Inhibition ofRas-targeted prenylation: protein farnesyl transferase inhibitors revisited. Grit. Rev. Oncol. Hematol (2000) 33:7–23.
  • HIGHTOWER K, CASEY PJ, FIERKE CA: Farnesylation of nonpeptidic thiol compounds by protein farnesyl-transferase. Biochemistry (2001) 40:1002–1010.
  • MORGAN B, ZAKS A, DODDS DR, LIU J, JAIN R, MEGATI S et al.: Enzymatic kinetic resolution of atropisomers: synthesis of a key intermediate of the farnesyl protein transferase inhibitor 5CH66336. j Org. Chem. (2000) 65:5451–5460.
  • FATOUROS D, GORTZI 0, KLEPETSANIS P, ANTIMISIRIASSG, STUART MCA, BRISSON A, IOANNOU PV: Prepara-tion and properties of arsonolipids containing liposomes. Chem. Phys. Lipids (2001) 109:75–89.
  • SUPURAN CT, SERVES SV, IOANNOU PV: Carbonic anhydrase inhibitors. Part 33 Isozyme II inhibition with 2,3-dihydroxypropylarsonic acids and arsonolipids.j Inorg. Biochem. (1996) 62:207–212.
  • TIMOTHEATOU D, IOANNOU PV, SCOZZAFAVA A, BRIGANTI F, SUPURAN CT: Carbonic anhydrase inhibi-tors. Part 42 Carbonic anhydrase interaction with © Ashley Publications Ltd. All rights reserved.Exp. Opin. Ther. Patents (2001) 11(5) lipothioarsenites: a novel class of isozymes I and II inhibitors. Metal Based Drugs (1996) 3:263–268.
  • IOANNOU PV, KORDALIS NL, SCOZZAFAVA A, SUPURAN CT: Carbonic anhydrase inhibitors. Part 87 Inhibition of carbonic anhydrase isozymes I, II and IV with arsinolipids. Main Group Met. Chem. (1999) 22:693–695.
  • DRINGEN R: Metabolism and functions of glutathione in brain. Progr. Neurobioi (2000) 62:649–671.
  • VAN BLADEREN PJ: Glutathione conjugation as a bioactivation reaction. Chem. Biol. Interact. (2000) 129:61–76.
  • LANDI S: Mammalian class theta GST and differentialsusceptibility to carcinogenesis: a review. Mutation Res. (2000) 463:247–283.
  • CONROY CW, SCHWAM H, MAREN TH: The non-enzymatic displacement of the sulfamoyl group from different classes of aromatic compounds by glutathione and cysteine. Drug Metab. Dispos. (1984) 12:614–618.
  • KISHIDA K, SAIDA N, YAMAMURA N, IWAI Y, SASABE T: cysteine conjugate of methazolamide is metabolized by 13-lyase. j Pharm. Sci. (2001) 90:224–233.
  • SUPURAN CT, SCOZZAFAVA A: Carbonic anhydrase inhibitors. Curr. Med. Chem. (2001):In press.
  • WOLTERSDORF W, SCHWAM H, BICKING JB et al.: Topically active carbonic anhydrase inhibitors. 1 O-Acyl derivatives of hydroxybenzothiazole-2-sulfonamide. J Med. Chem. (1989) 32:2486–2492.
  • IM WB, SIH JC, BLAKEMAN DP, MCGRATH JP: Omepra-zole, a specific inhibitor of gastric 11±/K+-ATP-ase, is an Htactivated oxidizing agent of sulfhydryls groups. J Biol. Chem. (1985) 260:4591–4597.
  • SACHS G, SHIN JM, BRIVING C, WALLMARK B, HERSEY S: The pharmacology of the gastric acid pump: the H+/K+-ATP-ase. Ann. Rev. Pharmacol. Toxicol. (1995) 35:277–305.
  • SUPURAN CT, BRIGANTI F, SCOZZAFAVA A: Sulfenamido-sulfonamides as inhibitors of carbonic anhydrase isozymes I, II and IV. J Enz. Inhib. (1997) 12:175–190.
  • SCOZZAFAVA A, SUPURAN CT: Carbonic anhydrase inhibitors. Novel compounds containing S-NH moieties in their molecule: sulfenamido-sulfonamides, sulfenimido-sulfon amides and their interaction with isozymes I, II and IV. J Enz. Inhib. (1998) 13:419–442.
  • MALLIS RJ, POLAND BW, CHATTERJEE TK et al.: Crystal structure of S-glutathiolated carbonic anhydrase III. FEBS Lett. (2000) 482:237–241.
  • ANDERSON PM, KORTE JJ, HOLCOMB TA, CHO YG, SON CM, SUNG YC: Formation of intersubunit disulfide bonds and properties of the single histidine and cysteine residues in each subunit relative to the decameric structure of cyanase. J Biol. Chem. (1994) 269:15036–15045.
  • SHARMA HK: The fast-reacting sulfhydryl group of ratmuscle phosphoglycerate kinase is necessary for activity and maintenance of tertiary structure. Biochemistry (1982) 21:6661–6668.
  • CZERSKI L, SANDERS CR: Thiol modifications ofdiacylglycerol kinase: dependence upon site membrane disposition and reagent hydrophobicity. FEBS Lett. (2000) 472:225–229.
  • REDDY S, JONES AD, CROSS CE, WONG PS, VAN DERVLIET A: Inactivation of creatine kinase by 5-glutathiolation of the active site cysteine residue. Biochem. J. (2000) 347:821–827.
  • FENG YH, SAAD Y, KARNIK SS: Reversible inactivation of AT2 angiotensin II receptor from cysteine-disulfide bond exchange. FEBS Lett. (2000) 484:133–138.
  • HASHIMOTO M, MAJIMA E, HATANAKA T et al.: Irreversible extrusion of the first loop facing the matrix of the bovine heart mitochondrial ADP/ATP carrier by labeling Cys56 residue with the SH reagent methyl methanethiosulfonate. J. Biochem. (Tokyo) (2000) 127:443–449.
  • LOO TW, CLARKE DM: Blockage of drug resistance in vitro by disulfiram, a drug used to treat alcoholism. J Nati Cancer Inst. (2000) 92:898–902.
  • LOO TVV, CLARKE DM: Determining the structure and mechanism of the human multidrug resistance P-glycoprotein using cysteine-scanning mutagenesis and thiol modifications techniques. Biochim. Biophys. Acta (1999) 1461:315–325.
  • MALLIS RJ, THOMAS JA: Effect of 5-nitrosothiols on cellular glutathione and reactive protein sulfhydryls. Arch. Biochem. Biophys. (2000) 383:60–69.
  • SHEN XM, DRYHURST G: Influence of glutathione on the oxidation chemistry of 5-S-cysteinyldopamine: potentially neuroprotective reactions of relevance to Parkinson's disease. Tetrahedron (2001) 57:393–405.
  • NAISBITT DJ, VILAR FJ, STALFORD AC, WILKINS EGL,PIRMOHAMED M, PARK BK: Plasma cysteine deficiency and decreased reduction of nitrososulfamethoxazole in HIV infection. AIDS Res. Hum. Retrov. (2000) 16:1929–1938.
  • CAVALLINI L, ALEXANDRE A: Oral N-acetylcysteineincreases the production of anti-HIV chemokines in peripheral blood mononuclear cells. Life Sci. (2000) 67:147–154.
  • SENGLE G, JENNE A, ARORA PS et al.: Synthesis,incorpo-ration efficiency and stability of disulfide bridged functional groups at RNA 5'-ends. Bioorg. Med. Chem. (2000) 8:1317–1329.

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