Advanced search
Publication Cover
Expert Opinion on Investigational Drugs Volume 5, 1996 - Issue 8
Submit an article Journal homepage
13
Views
2
CrossRef citations to date
0
Altmetric
Original Article

Section Reviews; Anti-infectives: Section Review Anti-infectives: Quinolone antibacterials and derivatives as antineoplastic agents

John F Barrett The RW Johnson Pharmaceutical Research Institute, Raritan, NJ, 08869, USA
Pages 1021-1031 | Published online: 03 Mar 2008

References to Primarv Literature

  • HOOPER DC, WOLFSON JS: Mechanism of quinolone action and bacterial killing. In: Quinolone Antimicrobial Agents, 2nd Edition. Hooper DC, Wolson JS (Eds.), Am. Soc. Micro biol. Washington, DC (1993):53–75.
  • SATO K, HOSHINO K, MITSUHASHI S: Mode of action of new quinolones: the inhibitory activity of DNA gyrase. Proc. Drug. Res. (1992):121–132.
  • GOOTZ TD, BARRETT JF, MCGUIRK PR, HOLDEN HE, RAY VE: Selective toxicity: the activities of 4-quinolones against eukaryotic topoisomerases. In: International Symposium on Quinolone Antibacterials. Crumplin GF (Ed.), Springer-Verlag, London (1990):159–172.
  • GOOTZ TD, BARRETT JF, SUTCLIFFE JA: Inhibitory effects of quinolone antibacterials on eukaryotic topoisom-erases and related test systems. Antimicrob. Agents Chemother. (1990) 34:8–12.
  • HOSHINO K, SATO K, AKAHANE K et al.: Significance ofthe methyl group on the oxazine ring of ofloxacin derivatives in the inhibition of bacterial and mammal-ian type II topoisomerases. Antimicrob. Agents Chenzother. (1991) 35:309–312.
  • BARRETT JF, GOOTZ TD, MCGUIRK PR, FARRELL CA, SOKOLOWSKI SA: Use of in vitro topoisomerase II assays for studying quinolone antibacterial agents. Antimicrob. Agents Chemother. (1989) 33(10):1697–1703.
  • WENTLAND MP, LESHER GY, REUMAN M et al.: Mammal-ian topoisomerase II inhibitory activity of 1-cyclo-pr o py1-6,8-difluor o- 1,4 -dihydr o -7-(2,6-dimethyl-4-pyridiny1)-4-oxo-3-quinollne carbox-ylic acid and related derivatives. J. Med. Chem. (1993) 36:2801–2809.
  • ELSEA SH, MCGUIRK PR, GOOTZ TD, MOYNIHAN MS,OSHEROFF N: Drug features that contribute to the activ-ity of quinolones against mammalian topoisomezase II and cultured cells: correlation between enhancement of enzyme-mediated DNA cleavage in vitro and cyto-toxic potential. Antimicrob. Agents. Chemother, (1993) 37(10):2179–2186.
  • ROBINSON MJ, ELSEA SH, MARTIN BA et al.: A novel quinolone with potent activity against eukaryotic DNA topoisomerase IL Proceedings Int. Symp. Mol. Biol. DNA Topoisomerases Its. Appl. Chemother. Andoh T, Ikeda H, Oguro M (Eds.), CRC Press, Boca Raton, FL (1993):189–198.
  • LIU LF: DNA topoisomerase poisons as antitumor drugs. Ann. Rev. Biochern. (1989) 58:351–375.
  • RADL S, DAX S: Quinolone congeners as mammaliantopoisomerase II inhibitors. Curr. Med. Chem. (1994) 1(4):262–270.
  • BERGEVIN P: New cancer chemotherapeutic agents. Drugs of Today (1987) 23:421–432.
  • FARMER PB: Cancer chemotherapy L Design and mecha-nism of action of cytotoxic drugs. In: The Molecular Basis of Cancer. Farmer PB, Walker JM (Eds.), John Wiley & Sons (1985):259–285.
  • ROSE KM: DNA topoisomerases as targets for chemo-therapy. FASEB J. (1988) 2:2474–2478.
  • PULLMAN B: A few considerations on quinones as anti-tumor agents. Int. J. Quantum Chem. (1986) 13:95–105.
  • MORRISON A, HIGGINS NP, COZZARELLI NR: Interactionbetween DNA gyrase and its cleavage site on DNA. J. Biol. Chem. (1980) 255:2211–2219.
  • BIGIONI M, ZUNINO F, CAPRANICO G: Base mutationanalysis of topoisomerase II-idarubkin-DNA ternary complex formation. Evidence for enzyme subunit co-operativity in DNA cleavage. Nucleic Acid Res. (1994) 22:2274–2281.
  • TEWEY KM, CHEN GL, NELSON EM, LIU LF: Intercalativ-eantitumor drugs interfere with the breakage-reunion reaction of mammalian topoisomerase 11. J. Biol. Chem. (1984) 259:9182–9187.
  • FOSSE P. RENE B, LEBRET M, PAOLETTI C, SAUCIER J-M: Sequence requirements for mammalian topoisomerase II mediated DNA cleavage stimulated by an ellipticine derivative. Nucleic Acid Res. (1991) 19:2861–2868.
  • VOSBERG H-P: DNA topoisomerases: enzymes that con-trol DNA conformation. Curr. Topics Micro biol. Immunol. (1985) 114:19–102.
  • MAXWELL A, GELLERT M. Mechanistic aspects of DNAtopoisomerases. Adv. Prot. Chem. (1986) 38:69–107.
  • NELSON EM, TEWEY KM, LIU LF: Mechanism of antitumordrug action poisoning of mammalian DNA topoisom-erase II on DNA by 4'-(9-acridinylamino)-methanesul-fon-m-anisidide. Proc. Natl, Acad. Sci. USA (1984) 81:1361–1365.
  • LUND K, ANDERSEN AH, CHRISTIANSEN K, SVEJSTRUP JQ,WESTGAARD O: Minimal DNA requirements for topo-isomerase 1I-mediated cleavage in vitro. J. Biol. Chem. (1990) 265:13856–13863.
  • AUSTIN CA, BAROT HA, MARGERRISON EEC et al.: Struc-ture and partial amino acid sequence of calf thymus DNA topoisomerase 11: comparison with other type II enzymes. Biochem. Biophys. Res. Comm. (1990) 170:763–768.
  • FOSSE P, PAOLETTI C, SAUCIER J-M: Pattern of recogni-tion of DNA by mammalian DNA topoisomerase IL Biochem. Biophys. Res. Comm. (1988) 151:1233–1240.
  • SUTO MJ, DOMAGALA JM, ROLAND GE, MAILLOUX GB,COHEN MA: Fluoroquinolones: relationships between structural variations, mammalian cell cytotoxlcity and antimicrobial activity. J. Med. Chem. (1992) 35(25):4745–4750.
  • ANDOII T, SATO M, NARITA T, ISHIDA R: Role of DNA topoisomerase II in chromosome dynamics in mam-malian cells. Biotechnol. Appl. Biochem. (1993) 18:165–174.
  • SUMMER AT: The distribution of topoisomerase 11 on mammalian chromosomes. Chromosome Res. (1996) 4:5–14.
  • DRLICA K: Biology of bacterial deoxyribonucleic acid topoisomerases. Microb. Rev. (1984) 48:273–289.
  • GASSER SM, WALTER R, DANG Q, CARDENAS ME: Topoi-somerase II: its function and phosphorylation. Antonie van Leeuwenhoek (1992) 62:15–24.
  • ROBINSON MJ, OSHEROFF N: Stabilization of the topoi-somerase II-DNA complex by antineoplastic drugs: in-hibition of enzyme-mediated DNA relegation by 4'-(9-acridinylamino)methanesulfon-m-anisidide. Bio-chemistry (1990) 29:2511–2515.
  • PAOLETTI C: The localization of topoisomerase 11 cleavage sites on DNA in the presence of antitumor drugs. Pharmacol. Ther. (1993) 60(2):381–387.
  • HUFF AC, ROBINSON RG, EVANS AC et al.: DNA sequence preferences at sites cleaved by human topoisomerase II in response to novel quinolone derivatives. Anti-Can-cer Drug Des. (1995) 10(3):251–276.
  • OSHEROFF N, CORBETT AH, ELSEA SH, WESTERGARD M: Defining functional drug-interaction domains on topo-isomerase 11 by exploiting mechanistic differences be-tween drug classes. Cancer Chemother. Pharmacol. (1994) 34(Suppl.):S19–S25.
  • HUFF AC, KREUZER KN: Evidence for a common mecha-nism of action for antitumor and antibacterial agents that inhibit type 11 DNA topoisomerases. J. Biol. Chem. (1990) 265(33):20496–20505.
  • BREDBERG A, BRANT M, JASZYK M: Ciprolioxacin-in-duced inhibition of topoisomerase II in human lym-phoid cells. Antimicrob. Agents Chemother. (1991) 35(3):448–450.
  • SIOUD M, FORTERRE P: Ciprofloxacin and etoposide (VP-16) produce a similar pattern of DNA cleavage in a plasmid of an archaebacterium. Biochemistty (1989) 28(9):3638–3641.
  • HAILER J, BURGESS R, DAWSON D: Increased cytotoxic-ity of squamous cell carcinoma of the head and neck by combining cisplatin with VP-16 and ciprofloxacin. La-iyngoscope (1993) 103(10):1081–1083.
  • YAMASHITA Y, ASHIZAWA T, MORIMOTO M, HOSOMI J, NAICANO H: Antitumor quinolones with mammalian topoisomerase II mediated DNA cleavage activity. Can. Res. (1992) 52(10):2818–2822.
  • OLMSTEAD ECK, CHOI YS, LEE JO, CHUN MW: Structure-activity relationship studies of cytotoxic 5-hydroxy-4-quinolone. 210th Meeting Am. Chem. Soc. Chicago (August 20–24, 1995).
  • GOOTZ TD, MCGUIRK PR, MOYNIHAN MS, HASKELL SL: Placement of alkyl substituents on the C-7 piperazine ring of fluoroquinolones: dramatic differential effects of mammalian topoisomerase 11 and DNA gyrase. An-timicrob. Agents. Chemother. (1994) 38(1):130–133.
  • FROELICH-AMMON SJ, MCGUIRK PR, GOOTZ TD, JEFSON MR, OHEROFF N: Novel 1-8-bridged chiral quinolones with activity against topoisomerase stereospecificity of the eukaryotic enzyme. Antimicrob. Agents. Chemother. (1993) 37(4):646–651.
  • KO TS, KWON TI, KIM MJ, PARK IH, RYU HW: Transition-metal-mediated cytotoxichy of quinolones to L1210 cells. Korean Chem Soc. (1994) 15(6):442–448.
  • HAMEL E, LIN CM, PLOWMAN J et at: Antitumor 2,3-dihy-dro-2-(ary1)-4(110quinazolinone derivatives. Interac-tions with tubulin. Biochem. Pharmacol. (1996) 51(1):53–59.
  • KUO SC, LEE HZ, JUANG JP et al.: Synthesis and cytotoxic-ity of 1,6,7,8-substituted 2-(4'-substituted phenyl)-4-qui-nolones and related compounds: identification as antimitotic agents interacting with tubulin. J. Med. Chem. (1993) 36(9):1146–1156.
  • LI L, WANG H-K, KUO S-C et al.: Antitumor agents. 155. Synthesis and biological evaluation of 3',6,7-substituted 2-phenyl-4-quinolones as antineoplastic agents. J. Med. Chem. (1994) 37(20):3400–3407.
  • LI L, WANG H-K, KUO S-C et al.: Antitumor agents. 150.2-phenyl-4-quinolones and related compounds: their synthesis, cytotoxlcity, and Inhibition of tubulin polymerization. J. Med. Chem. (1994) 37(8):1126–1 135.
  • CHU DTW, HALLAS R, TANAKA SK et al.: Synthesis and antitumor activities of tetracyclic quinolone antineo-plastic agents. Drugs Exp. Clin. Res. (1994) 20(5):117–183.
  • FAN J-Y, SUN D, YU H, KERWIN SM, HURLEY LH: Self-as-sembly of a quinobenzoxazine-Mg2+ complex on DNA: a new paradigm for the structure of a drug-DNA com-plex and implications for the structure of the quinolone bacterial gyrase-DNA complex. J. Med. Chem. (1995) 38(3):408–424.
  • CHU DTW, HALLAS R, CLEMENT JJ et al.: Synthesis and antinunor activities of quinolone antineoplastic agents. Drugs Exp. Clin. Res. (1992) 18(7):275–282.
  • PERMANA PA, SNAPKA RM, SHEN LL et al.: Quinoben-zoxazines: a class of novel antitumor quinolones and potent mammalian DNA topoisomerase II catalytic in-hibitors. Biochemistry (1994) 33(37):11333–11339.
  • KOHLBRENNER WE, WIDEBURG N, WEIGL D, SALDIVAR A, CHU DTW: Induction of calf thymus topoisomerase II-mediated DNA breakage by the antibacterial isothia-zoloquinolones A-65281 and A-65282. Antimicrvb. Agents Chemother. (1992) 36(1):81–86.
  • CLEMENT JJ, BURRES N, JARVIS K et al.: Biological char-acterization of a novel antitumor quinolone. CancerRes. (1995) 55(4):830–835.
  • YOSHINARI T, MANO E, ARAKAWAH et al.: Stereo (C7)-dependent topoisomerase II inhibition and tumour growth suppression by new quinolone, BO-2367. jpn. J. Cancer Res. (1993) 84(7):800–806.
  • SPITZNER JR, CHUNG IK, GOOTZ TD, MCGUIRK PR, MULLER MT: Analysis of eukaryotic topoisomerase II cleavage sites in the presence of the quinolone CP-115,953 reveals drug-dependent and -independent rec-ognition elements. MoL Pharrnacol. (1995) 48(2):238–249.
  • ROBINSON MJ, MARTIN BA, GOOTZ TD, MCGUIRK PR, OSHEROFF N: Effects of novel ftuoroquinolones on the catalytic activities of eukaryotic topoisomerase II: influ-ence of the C-8 fluorine group. Antimicn9b. Agents Chemother. (1992) 36(4) :751–756 .
  • ROBINSON MJ, MARTIN BA, GOOTZ TD et al.: Effects ofquinolone derivatives on eukaryotic topoisomerase 11. A novel mechanism for enhancement of enzyme-me-diated DNA cleavage. J. Biol. Chem. (1991) 266(22):14585–14592.
  • CORBETT All, GUERRY P, PFLIEGER P, OSHEROFF N: Apyrimido[1,6-a]benzimidazole that enhances DNA cleavage mediated by eukaryotic topoisomerase II: a novel class of topoisomerase II-targeted drugs with cytotoxic potential. Antimicrob. Agents Chemother. (1993) 37:2599–2605.
  • COUGHLIN SA, DANZ DW, ROBINSON RG et al.: Mecha-nism of action and antitumor activity of (S)-10-(2,6-di-methy1-4-pyridinyl) -9-fluoro-3-methy1-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-d,e111,4]benzothiazine-6-carb-oxylic add (WIN 58161). Biochem. Pharmacol. (1995) 50(1):111–122.
  • EISSENSTAT MA, KUO G-H, WEAVER JD III et al.: 3-Benzyl-quinolones: novel, potent inhibitors of mammalian topoisomerase IL Bioorg. Med. Chem. Lett. (1995) 5(9):1021–1026.

References to Primarv Literature

  • LEE KH, KUO SC, WU TS et al. (GENELABS TECHNOLOGIES, INC., THE UNIVERSITY OF NORTH CAROLINA): 2-ary1-4-quinolones as antitumor compounds. W09402145-A (1994)
  • EISSENSTAT MA, WEAVER JD III, KUO GH, WENTLAND MP (STERLING WINTHROP, INC.): 1-Cyclopropy1-4-pyridyl-quinolones. US5330992-A (1992).
  • ITO Y, KATO H, YASUDA S et al. (HOKURIKU PHARMA-CEUTICALS): Preparation of 7-(5-azaspiro12,41heptan-5-y1)-8-alkoxyquinolone-3-carboxylic acids as pharmaceuticals. JP06049059-A (1992).
  • ITO Y, KATO H, YASHUDA S et al. (HOKURIKU PHARMA-CEUTICALS) Preparation of 7-(4,4-dialky1-3-aminopyr-rolidinyl)quinolone-3-carboxylic acids as pharmaceuticals. JP05345777-A (1992).
  • NAKANO H, YAMASHITA N, ASHIZAWA T et al. (KYORIN PHARMACEUTICAL CO.) Anticancer agents containing quinolonecarboxylic adds. JP03024013-A (1989).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.