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Review Article

Topoisomerase as target for antibacterial and anticancer drug discovery

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Pages 419-435 | Received 29 Dec 2011, Accepted 16 Jan 2012, Published online: 01 Mar 2012

References

  • Wang JC. Cellular roles of DNA topoisomerases: A molecular perspective. Nat Rev Mol Cell Biol 2002;3:430–440.
  • Wang JC. DNA topoisomerases. Annu Rev Biochem 1996;65:635–692.
  • Fritz Boege. Analysis of eukaryotic DNA topoisomerases and topoisomerase-directed drug effects. Eur J Clin Chem Clin Biochem 1996;34:873–888.
  • Merino A, Madden KR, Lane WS, Champoux JJ, Reinberg D. DNA topoisomerase I is involved in both repression and activation of transcription. Nature 1993;365:227–232.
  • Kretzschmar M, Meisterernst M, Roeder RG. Identification of human DNA topoisomerase I as a cofactor for activator-dependent transcription by RNA polymerase II. Proc Natl Acad Sci USA 1993;90:11508–11512.
  • Zhang H, Wang JC, Liu LF. Involvement of DNA topoisomerase I in transcription of human ribosomal RNA genes. Proc Natl Acad Sci USA 1988;85:1060–1064.
  • Lim M, Liu LF, Jacobson-Kram D, Williams JR. Induction of sister chromatid exchanges by inhibitors of topoisomerases. Cell Biol Toxicol 1986;2:485–494.
  • Shuman S. Recombination mediated by vaccinia virus DNA topoisomerase I in Escherichia coli is sequence specific. Proc Natl Acad Sci USA 1991;88:10104–10108.
  • Yeh YC, Liu HF, Ellis CA, Lu AL. Mammalian topoisomerase I has base mismatch nicking activity. J Biol Chem 1994;269:15498–15504.
  • Stevnsner T, Bohr VA. Studies on the role of topoisomerases in general, gene- and strand-specific DNA repair. Carcinogenesis 1993;14:1841–1850.
  • Nitiss JL. Roles of DNA topoisomerases in chromosomal replication and segregation. Adv Pharmacol 1994;29A:103–134.
  • Earnshaw WC, Mackay AM. Role of nonhistone proteins in the chromosomal events of mitosis. FASEB J 1994;8:947–956.
  • Earnshaw WC, Heck MM. Localization of topoisomerase II in mitotic chromosomes. J Cell Biol 1985;100:1716–1725.
  • Earnshaw WC, Halligan B, Cooke CA, Heck MM, Liu LF. Topoisomerase II is a structural component of mitotic chromosome scaffolds. J Cell Biol 1985;100:1706–1715.
  • Jorge BS, Andrzej S. A topological view of the replicon. EMBO reports 2004;5:256–261.
  • Losada A, Hirano T. Shaping the metaphase chromosome: Coordination of cohesion and condensation. Bioessays 2001;23:924–935.
  • Paul MW, Ian DH. Structure and function of type 11 DNA topoisomerases. Biochem J 1994;303:681–695.
  • D’Arpa P, Machlin PS, Ratrie H 3rd, Rothfield NF, Cleveland DW, Earnshaw WC. cDNA cloning of human DNA topoisomerase I: Catalytic activity of a 67.7-kDa carboxyl-terminal fragment. Proc Natl Acad Sci USA 1988;85:2543–2547.
  • Juan CC, Hwang JL, Liu AA, Whang-Peng J, Knutsen T, Huebner K et al. Human DNA topoisomerase I is encoded by a single-copy gene that maps to chromosome region 20q12-13.2. Proc Natl Acad Sci USA 1988;85:8910–8913.
  • Lima CD, Wang JC, Mondragón A. Three-dimensional structure of the 67K N-terminal fragment of E. coli DNA topoisomerase I. Nature 1994;367:138–146.
  • Li TK, Liu LF. Tumor cell death induced by topoisomerase-targeting drugs. Annu Rev Pharmacol Toxicol 2001;41:53–77.
  • David SG. The molecular perspective: DNA topoisomerases 2002;7:381–382.
  • David FF, Clemencia P, Anca MS. New peptide inhibitors of type IB topoisomerases: Similarities and differences inhibitors of tyrosine recombinases. J Mol Biol 2006;363:891–907.
  • Taneja B, Patel A, Slesarev A, Mondragón A. Structure of the N-terminal fragment of topoisomerase V reveals a new family of topoisomerases. EMBO J 2006;25:398–408.
  • Malte W, Etienne W, Alfred ME. Combining EL4-B5-based B-cell stimulation and phage display technology for the successful isolation of human anti-Scl-70 autoantibody fragments. J Immun Method 2003;278:249–259.
  • Willmore E, de Caux S, Sunter NJ, Tilby MJ, Jackson GH, Austin CA et al. A novel DNA-dependent protein kinase inhibitor, NU7026, potentiates the cytotoxicity of topoisomerase II poisons used in the treatment of leukemia. Blood 2004;103:4659–4665.
  • Tan KB, Dorman TE, Falls KM, Chung TD, Mirabelli CK, Crooke ST et al. Topoisomerase II alpha and topoisomerase II beta genes: Characterization and mapping to human chromosomes 17 and 3, respectively. Cancer Res 1992;52:231–234.
  • Liu LF, Liu CC, Alberts BM. Type II DNA topoisomerases: Enzymes that can unknot a topologically knotted DNA molecule via a reversible double-strand break. Cell 1980;19:697–707.
  • Edward G, Karl D. Regulation of bacterial DNA supercoiling: Plasmid linking numbers vary with growth temperature (DNA topology/gel electrophoresis), Biochemistry 1984;81:4046–4050.
  • Raji A, Zabel DJ, Laufer CS, Depew RE. Genetic analysis of mutations that compensate for loss of Escherichia coli DNA topoisomerase I. J Bacteriol 1985;162:1173–1179.
  • Wang JC. Interaction between DNA and an Escherichia coli protein omega. J Mol Biol 1971;55:523–533.
  • Tse-Dinh YC, Wang JC. Complete nucleotide sequence of the topA gene encoding Escherichia coli DNA topoisomerase I. J Mol Biol 1986;191:321–331.
  • Yu CX, Zhu YC, Tse-Dinh Fesik, SW. Solution structure of the C-terminal single-stranded DNA-binding domain of E. coli topoisomerase I. Biochemistry 1995;34:7622–7628.
  • David CH. Bacterial topoisomerases, anti topoisomerases, and anti topoisomerase resistance. Clin Inf Diseases 1998;27 (Suppl 1):S54–63.
  • Changela A, DiGate RJ, Mondragón A. Structural studies of E. coli topoisomerase III-DNA complexes reveal a novel type IA topoisomerase-DNA conformational intermediate. J Mol Biol 2007;368:105–118.
  • Joseph AH. DNA topoisomerases as anticancer drug targets: From the laboratory to the clinic. Curr Med Chem Anticancer Agents 2001;1:1–25.
  • Kato J, Suzuki H, Ikeda H. Purification and characterization of DNA topoisomerase IV in Escherichia coli. J Biol Chem 1992;267:25676–25684.
  • Peng H, Marians KJ. Escherichia coli topoisomerase IV. Purification, characterization, subunit structure, and subunit interactions. J Biol Chem 1993;268:24481–24490.
  • Maxwell A. DNA gyrase as a drug target. Trends Microbiol 1997;5:102–109.
  • Schmutz E, Mühlenweg A, Li SM, Heide L. Resistance genes of aminocoumarin producers: Two type II topoisomerase genes confer resistance against coumermycin A1 and clorobiocin. Antimicrob Agents Chemother 2003;47:869–877.
  • Nelson JM, Chiller TM, Powers JH, Angulo FJ. Fluoroquinolone-resistant Campylobacter species and the withdrawal of fluoroquinolones from use in poultry: A public health success story. Clin Infect Dis 2007;44:977–980.
  • Ivanov DV, Budanov SV. Ciprofloxacin and antibacterial therapy of respiratory tract infection. Antibiot Khimioter 2006;51:29–37.
  • Fisher LM, Pan XS. Methods to assay inhibitors of DNA gyrase and topoisomerase IV activities. Methods Mol Med 2008;142:11–23.
  • Gore J, Bryant Z, Stone MD, Nöllmann M, Cozzarelli NR, Bustamante C. Mechanochemical analysis of DNA gyrase using rotor bead tracking. Nature 2006;439:100–104.
  • Yasuhiro K, Kazuto N. Mechanisms of action of cancer chemo therapeutic agents: Topoisomerase inhibitors. John Wiley & Sons, Ltd. 2002:2–7.
  • Joyce M, Nirmala A. Samundeeswari, Deepa Sankar, P. Natural plant resources in anti-cancer therapy-A review. Research in Plant Biology 2011;1:01–14.
  • Chalet Tan. Topoisomerases inhibitor. PHA 557. HemeOnc, 2009.
  • Benchokroun Y, Couprie J, Larsen AK. Aurintricarboxylic acid, a putative inhibitor of apoptosis, is a potent inhibitor of DNA topoisomerase II in vitro and in Chinese hamster fibrosarcoma cells. Biochem Pharmacol 1995;49:305–313.
  • Devendra ST. Topoisomerase II inhibitors in cancer treatment. Int J Pharm Sci Nanotechnology 2011;3:1174–1179.
  • Ferrer S, Marce B, Bellosillo N, Villamor F. Activation of mitochondiral apoptotic pathway in mantel cell lymphoma: High sensitivity to mitoxantrone in cases with functional DNA-damage response genes. Oncogene 1991;23:8941–8949.
  • Felix CA. Leukemias related to treatment with DNA topoisomerase II inhibitors. Med Pediatr Oncol 2001;36:525–535.
  • Takimoto CH, Calvo E, Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (eds.) “Principles of Oncologic Pharmacotherapy” in Cancer Management: A Multidisciplinary Approach, 11th edn. 2008.
  • Wall ME, Wani MC, Cook CE, Palmer KH, McPhail AI, Sim GA. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from camptotheca acuminate. J Am Chem Soc 1966;88:3888–3890.
  • Mi Z, Malak H, Burke TG. Reduced albumin binding promotes the stability and activity of topotecan in human blood. Biochemistry 1995;34:13722–13728.
  • Barth, Stephan, Briviba, Esselen. In vivo bioassay to detect irinotecan-stabilized DNA/topoisomerase I complexes in rats. Biotechnology Journal Wiley-VCH 2009:2–26.
  • Yves P. Camptothecins and topoisomerase I: A Foot in the Door, p. 1.
  • Adams DJ. The impact of tumor physiology on camptothecin-based drug development. Curr Med Chem Anticancer Agents 2005;5:1–13.
  • Zunino F, Dallavalleb S, Laccabuea D, Berettaa G, Merlinib L, Pratesi G. Current status and perspectives in the development of camptothecins. Curr Pharm Des 2002;8:2505–2520.
  • Ulukan H, Swaan PW. Camptothecins: A review of their chemotherapeutic potential. Drugs 2002;62:2039–2057.
  • Chung MK, Han SS, Kim JC. Evaluation of the toxic potentials of a new camptothecin anticancer agent CKD-602 on fertility and early embryonic development in rats. Regul Toxicol Pharmacol 2006;45:273–281.
  • Christian B. Homocamptothecins: Potent topoisomerase I inhibitors and promising anticancer drugs. Critical Reviews in Oncology/Hematology 2003;45:91–108.
  • Meng LH, Liao ZY, Pommier Y. Non-camptothecin DNA topoisomerase I inhibitors in cancer therapy. Curr Top Med Chem 2003;3:305–320.
  • Antony S, Jayaraman M, Laco G, Kohlhagen G, Kohn KW, Cushman M, Pommier Y. Progress in nucleic acid research and molecular biology. Cancer Res 2003;63:7428.
  • Cheng P, Zhu L, Guo W, Liu W, Yao J, Dong G, Zhang Y, Zhuang C, Sheng C, Miao Z, Zhang W. Synthesis of novel benzoxanthone analogues as non Camptothecin. J Enzyme Inhib Med Chem 2011;20:1–5.
  • Gerrits CJ, de Jonge MJ, Schellens JH, Stoter G, Verweij J. Topoisomerase I inhibitors: The relevance of prolonged exposure for present clinical development. Br J Cancer 1997;76:952–962.
  • Moore MJ, Siu LL, Oza A et al. 9-aminocamptothecin (9AC) given by 24 hour infusion once weekly. A phase I pharmacokinetic (PK) and pharmacodynamic (PD) study. Proc Am Soc Clin Oncol 1997;16:200a.
  • Reginald B., Ewesuedo, Mark J., Ratain. Topoisomerase I inhibitors. The Oncologist 1997;2:359–364.
  • Kanzawa F, Nishio K, Kubota N, Saijo N. Antitumor activities of a new indolocarbazole substance, NB-506, and establishment of NB-506-resistant cell lines, SBC-3/NB. Cancer Res 1995;55:2806–2813.
  • Ren J, Bailly C, Chaires JB. NB-506, an indolocarbazole topoisomerase I inhibitor, binds preferentially to triplex DNA. FEBS Lett 2000;470:355–359.
  • Ohkubo M, Nishimura T, Honma T, Nishimura I, Ito S, Yoshinari T et al. Synthesis and biological activities of NB-506 analogues: Effects of the positions of two hydroxyl groups at the indole rings. Bioorg Med Chem Lett 1999;9:3307–3312.
  • Kassoum N, Conxiang CZ, Peter R, Guzzo R, Jason H, Denise P, Thomas DF. Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted luotonin A derivatives. Bioorg Med Chem, 2007;15:4237–4246.
  • Renuka D, Nutan M. Furanocoumarins: Novel topoisomerase I inhibitors from Ruta graveolens L. Bioorg Med Chem 2009;17:7052–7055.
  • Kiselev E, DeGuire S, Morrell A, Agama K, Dexheimer TS, Pommier Y et al. 7-azaindenoisoquinolines as topoisomerase I inhibitors and potential anticancer agents. J Med Chem 2011;54:6106–6116.
  • John LN. Targeting DNA topoisomerase II in cancer chemotherapy. Nat Rev Cancer 2009;9:338–350.
  • Stacie J. Froelich-Ammon and Neil Osheroff. Topoisomerase poisons: Harnessing the dark side of enzyme mechanism. J Biol Chem 270:21429–21432.
  • Nitiss JL, Beck WT. Antitopoisomerase drug action and resistance. Eur J Cancer 1996;32A:958–966.
  • Gewirtz DA. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem Pharmacol 1999;57:727–741.
  • Ferreira AL, Matsubara LS, Matsubara BB. Anthracycline-induced cardiotoxicity. Cardiovasc Hematol Agents Med Chem 2008;6:278–281.
  • Roca J, Ishida R, Berger JM, Andoh T, Wang JC. Antitumor bisdioxopiperazines inhibit yeast DNA topoisomerase II by trapping the enzyme in the form of a closed protein clamp. Proc Natl Acad Sci USA 1994;91:1781–1785.
  • Tanabe K, Ikegami Y, Ishida R, Andoh T. Inhibition of topoisomerase II by antitumor agents bis(2,6-dioxopiperazine) derivatives. Cancer Res 1991;51:4903–4908.
  • Patrick C, Joëlle R, Joseph S. Catalytic inhibition of topoisomerase II by a novel rationally designed ATP-competitive purine analogue. BMC Chem Biol 2009;9:1.
  • Collins A. Topoisomerase II can relax; novobiocin is a mitochondrial poison after all. Bioessays 1990;12:493–494.
  • Drake FH, Hofmann GA, Mong SM, Bartus JO, Hertzberg RP, Johnson RK et al. In vitro and intracellular inhibition of topoisomerase II by the antitumor agent merbarone. Cancer Res 1989;49:2578–2583.
  • Chène P, Rudloff J, Schoepfer J, Furet P, Meier P, Qian Z et al. Catalytic inhibition of topoisomerase II by a novel rationally designed ATP-competitive purine analogue. BMC Chem Biol 2009;9:1.
  • Natalya MK, Michael S, Esther P, Ruth R, Eduard B, Mordechai C, Raphael M. HU-331, a novel cannabinoid-based anticancer topoisomerase II inhibitor. Mol cancer Ther 2007;6:173–183.
  • Natalya MK, Michael S, Maximilian P, Gergana M, Ronen B, Raphael M. A cannabinoid anticancer quinone, HU-331, and less is more powerful than cardiotoxic doxorubicin: A comparative in vivo study. J Pharmacol Exp Ther 2007;322:646–653.
  • Zunino F, Gambetta R, DiMarco A, Luoni G, Zaccara A. Effects of the stereochemical configuration on the interaction of some daunomycin derivatives with DNA. Biochem Biophys Res Commun 1976;69:744–750.
  • Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C et al. Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius. Biotechnol Bioeng 1969;11:1101–1110.
  • Sinha BK, Katki AG, Batist G, Cowan KH, Myers CE. Differential formation of hydroxyl radicals by adriamycin in sensitive and resistant MCF-7 human breast tumor cells: Implications for the mechanism of action. Biochemistry 1987;26:3776–3781.
  • Faulds D, Balfour JA, Chrisp P, Langtry HD. Mitoxantrone. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in the chemotherapy of cancer. Drugs 1991;41:400–449.
  • Crespi MD, Ivanier SE, Genovese J, Baldi A. Mitoxantrone affects topoisomerase activities in human breast cancer cells. Biochem Biophys Res Commun 1986;136:521–528.
  • Waksman SA, Woodruff HB. Bacteriostatic and bactericidal substances produced by a soil actinomyces. Proc Soc Exp Biol Med 1940;45:609.
  • Yu C, Tseng YY. NMR study of the solution conformation of actinomycin D. Eur J Biochem 1992;209:181–187.
  • Eric HR, William NH. (2000).Chapter 49 Anthracyclines and DNA Intercalators/Epipodophyllotoxins/DNA Topoisomerases, Cancer Medicine 5th edition. Hamilton, Ontario, Canada: BC Decker Inc.
  • Gordaliza M, García PA, del Corral JM, Castro MA, Gómez-Zurita MA. Podophyllotoxin: Distribution, sources, applications and new cytotoxic derivatives. Toxicon 2004;44:441–459.
  • Amy MW, Ryan PB, Murrell G, Sungjo C. Topoisomerase II-drug interaction domains: Identification of substituents on etoposide that interact with the enzyme. Biochemistry 2007;46:8217–8225.
  • Jinzhong L, Wantao C, Ping Z, Ningyi L. Topoisomerase II trapping agent teniposide induces apoptosis and G2/M or S phase arrest of oral squamous cell carcinoma. World J Surg Oncol 2006;4:41.
  • John DB, Eng SH. Two specific topoisomerase I inhibitors prevent replication of human cytomegalovirus DNA: An implied role in replication of the viral genome. J Virolog 1988;4797–4800.
  • Jo Ann WB, Susan DC, Teruhiro U. DNA topoisomerase II as the target for the anticancer drug TOP-53:  Mechanistic basis for drug action. Biochemistry 2001;40:712–718.
  • Rachael EH, David ES, Jo Ann WB. Voreloxin is an anticancer quinolone derivative that intercalates DNA and poisons topoisomerase II, PLoS ONE 2010;5:1–10.
  • Susan DC, Timothy LM, Neil O. Azatoxin is a mechanistic hybrid of the topoisomerase II-targeted anticancer drugs etoposide and ellipticine. Biochemistry 1997;36:13095–13101.
  • Pritam T, Radha K, Hoyoung C, Jae HC, Eung-Seok L et al. Synthesis of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure activity relationship. Bioorg Med Chem 2010;18:2245–2254.
  • Arjun B, Pritam T, Radha K, Hoyoung C, Jae Hun Choi Eung-Seok Lee et al. 2,6-Dithienyl-4-furyl pyridines: synthesis, topoisomerase I and II inhibition, cytotoxicity, structure–activity relationship, and docking study. Bioorg Med Chem Lett 2010;20:42–47.
  • Pritam T, Radha K, Uttam T, Yurngdong J, Eung-Seok L et al. 2-Thienyl-4-furyl-6-aryl pyridine derivatives: synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship study. Bioorg Med Chem 2010;18:377–386.
  • Radha K, Pritam T, Mi JK, Tae CJ, Jung MN, Eung-Seok L et al. Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure activity relationship study of hydroxylated 2,4-diphenyl-6-aryl pyridines. Bioorg Med Chem 2010;18:3066–3077.
  • Arjun B, Pritam T, Radha K, Chong-Soon L, Eung-Seok L et al. 2,4,6-Trisubstituted pyridines: synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship. Bioorg Med Chem 2007;15:4351–4359.
  • Al-Trawneh SA, El-Abadelah MM, Zahra JA, Al-Taweel SA, Zani F, Incerti M et al. Synthesis and biological evaluation of tetracyclic thienopyridones as antibacterial and antitumor agents. Bioorg Med Chem 2011;19:2541–2548.
  • Al-Trawneh SA, Zahra JA, Kamal MR, El-Abadelah MM, Zani F, Incerti M et al. Synthesis and biological evaluation of tetracyclic fluoroquinolones as antibacterial and anticancer agents. Bioorg Med Chem 2010;18:5873–5884.
  • Shi DK, Zhang W, Ding N, Li M, Li YX. Design, synthesis and biological evaluation of novel glycosylated diphyllin derivatives as topoisomerase II inhibitors. Eur J Med Chem 2012;47:424–431.
  • Kawatani M, Takayama H, Muroi M, Kimura S, Maekawa T, Osada H. Identification of a small-molecule inhibitor of DNA topoisomerase II by proteomic profiling. Chem Biol 2011;18:743–751.
  • Masashi Y, Ken-Ichiro H, Hiroshi H, Shogo I, Takuji H, Ken T et al. Stilbenoids of Kobresia nepalensis (Cyperaceae) exhibiting DNA topoisomerase II inhibition, Phytochemistry 2006;67:307–313.
  • Bensasson RV, Zoete V, Jossang A, Bodo B, Arimondo PB, Land EJ. Potency of inhibition of human DNA topoisomerase I by flavones assessed through physicochemical parameters. Free Radic Biol Med 2011;51:1406–1410.
  • Denny WA, Baguley BC. Dual topoisomerase I/II inhibitors in cancer therapy. Curr Top Med Chem 2003;3:339–353.

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