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Structure-activity relationships of quinolones

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Fluoroquinolone Antibiotics

Part of the book series: Milestones in Drug Therapy ((MDT))

Abstract

The first of the antiinfective agents belonging to the quinolone class was discovered 50 years ago. Since that time many thousands of analogs have been prepared and nearly two dozen examples have found clinical use. New agents are still being introduced at a significant pace and research continues to be intensive in this area. With the passage of time and the accretion of more and more evidence, a deeper understanding of how these agents work and the structural characteristics required for significant activity and freedom from toxicity has been achieved. The purpose of this chapter is to provide a summary view of the present state of the art. It is important, however, to bear in mind that several surprises have upset our confidence in the generality of conventional wisdom. This has occurred already several times in this therapeutic area and constitutes a warning against uncritical reliance on overinterpreted or generalized beliefs.

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References

  1. Teoh-Chan CH, Cowlishaw A, Eley A, Slater G, Greenwood D (1985) Laboratory evaluation of enoxacin: comparison with norfloxacin and nalidixic acid. JAntimicrob Chemother 15: 45–52

    CAS  Google Scholar 

  2. Ohshita Y, Hayashi N, Amano H, Hirao Y, Niino Y, Yazaki A, Kobayashi Y (1998) WQ-3034, A novel acidic fluoroquinolone: in vitro and in vivo antimicrobial activities. 38th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Diego. Poster F-084

    Google Scholar 

  3. Huczko E, Valera L, Conetta B, Stickle T, Macko A, Fung-Tomc J (1999) Susceptibility of bacterial isolates to gatifloxacin and ciprofloxacin from the clinical trails during the 1997–1998 Period. 39th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco. Poster F-0351

    Google Scholar 

  4. Fass RJ (1997) In vitro activity of Bay 12–8038, a new 8-methoxyquinolone. Antimicrob Agts Chemother 41: 1818–1824

    CAS  Google Scholar 

  5. Barry AL, Jones RN (1989) In vitro activities of tmafloxacin, tosufloxacin (A-61827) and five other fluoroquinolone agents. J Antimicrob Chemother 23: 527–35

    CAS  PubMed  Google Scholar 

  6. Wise R, Andrews JM (1999) Gemifloxacin: the in vitro activity and a tentative breakpoint of a new fluoroquinolone. 39th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco. Poster F-2309

    Google Scholar 

  7. Garey KW, Amsden GW (1999) Trovafloxacin: an overview. Pharmacotherapy 19: 21–34

    CAS  PubMed  Google Scholar 

  8. Wise R, Andrews JM, Matthews R, Wolstenholme M (1992) The in vitro activity of two new quinolones: rufloxacin and MF-961. JAntimicrob Chemother 29: 649–660

    CAS  Google Scholar 

  9. Morita S, Otsubo K, Uchida M, Kawabata S, Tamaoka H, Shimizu (1990) A synthesis and antibacterial activity of the metabolites of 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidyl)-5-methyl10-benzo[i.j]quinolizine-2-carboxylic acid (OPC-7251). Chem Pharm Bull 38: 2027–2029

    CAS  Google Scholar 

  10. Albrecht R (1977) Development of antibacterial agents of the nalidixic acid type. Prog Drug Res 21: 9–104

    CAS  PubMed  Google Scholar 

  11. Domegala J, Heifetz C, Siporin (eds) (1990) The new generation of quinolones. Marcel Dekker, Inc., New York

    Google Scholar 

  12. Radl S (1990) Structure-activity relationships in DNA gyrase inhibitors. Pharmac Ther 48: 1–17

    Google Scholar 

  13. Rosen T (1990) The fluoroquinolone antibacterial agents. Prog Med Chem 27: 235–295

    CAS  PubMed  Google Scholar 

  14. Wentland MP (1990) Structure-activity relationships of fluoroquinolones. In: J Domagala, C Heifetz, C Siporin (eds): The new generation of quinolones. Marcel Dekker, Inc., New York, 1–43

    Google Scholar 

  15. Mitscher LA, Devasthale P, Zavod R (1993) Structure-activity relationships. In: JS Wolfson, DC Hooper (eds): Quinolone antibacterial agents, 2nd ed. American Society for Microbiology, Washington, 3–52

    Google Scholar 

  16. Wolfson JS, Hooper DC (eds) (1993) Quinolone antibacterial agents, 2nd ed. American Society for Microbiology, Washington

    Google Scholar 

  17. Domagala JM (1994) Structure-activity and structure-side-effect relationships for the quinolone antibacterials. JAntimicrob Chemother 33: 685–706

    CAS  Google Scholar 

  18. Gootz TD, Brighty KE (1996) Fluoroquinolone antibacterials. Med Res Reversus 16: 433–86

    CAS  Google Scholar 

  19. Drlica K, Zhao X, (1997) DNA gyrase, topoisomerase IV, and the 4-quinolones, Microbiol Mol Biol Rev 61: 377–92

    CAS  Google Scholar 

  20. Brighty KE, Gootz TD (1997) The chemistry and biological profile of trovafloxacin. JAntimicrob Chemother 39 Suppl. B: 1–14

    Google Scholar 

  21. Andriole VT (ed) (1998) The Quinolones, 2nd ed. Academic Press, New York

    Google Scholar 

  22. Bonomo RA (1998) Fluoroquinolones. Clinical Microbiology Newsletter 20: 197–201

    Google Scholar 

  23. Blondeau JM (1999) Expanded activity and utility of the new fluoroquinolones: a review. Clin Ther 21: 3–40

    CAS  PubMed  Google Scholar 

  24. Rubenstein E (2001) History of quinolones and their side-effects. Chemotherapy 47, Suppl. 3: 3–8

    Google Scholar 

  25. Takemura M, Hayakawa I (2001) Recent advances in the field of quinolones. Farmaco 56: 37–40

    CAS  PubMed  Google Scholar 

  26. Peterson LR (2001) Quinolone molecular structure-activity relationships: what we have learned about improving antimicrobial activity. Clin Infect Dis 33 Suppl 3: S180–S186

    CAS  PubMed  Google Scholar 

  27. Kim OK, Ohemeng K, Barrett JF (2001) Advances in DNA gyrase inhibitors. Expert Opin Investig Drugs, 10: 199–212

    CAS  PubMed  Google Scholar 

  28. Berger JM, Gamblin SJ, Harrison SC, Wang JC (1996) Structure and mechanism of DNA topoisomerase II, Nature 379: 225–32

    CAS  PubMed  Google Scholar 

  29. Kato J, Nishimura Y, Imamura R, Niki H, Hiraga S, Suzuki H (1990) New topoisomerase essential for chromosome segregation in E. coli. Cell 63: 393–404

    CAS  PubMed  Google Scholar 

  30. Hanessian S, Saladino R, Nunez JC (1996) On the binding site of quinolone antibactrerials. An attempt to probe the Shen model. Biorg Med Chem Lett 6: 2333–8

    CAS  Google Scholar 

  31. Batori S, Timari G, Koczka I, Hermecz I (1996) Synthesis and biological evaluation of N(1-aziridino)-6-fluoroquinolone-3-carboxylic acids. Biorg Med Chem Lett 6: 1507–1510

    CAS  Google Scholar 

  32. Al-Masoudi NA, Al-Soud YA, Eherman M, Clercq ED (1998) Quinolone nucleoside: 6,7-dihalo-N-beta-and alpha-glycosyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids and derivatives. Synthesis, antimicrobial and antiviral activity. Nucleosides, Nucleotides 17: 2255–66

    CAS  Google Scholar 

  33. Al-Masoudi NA, Al-Soud YA, Eherman M, Clercq ED (2000) Synthesis of acyclic 6,7-dihaloquinolone nucleoside analogues as potential antibacterial and antiviral agents. Bioorg Med Chem 8: 1407–13

    CAS  PubMed  Google Scholar 

  34. Kawakami K, Takahashi H, Ohki H, Kimura K, Miyauchi S, Miyauchi R, Takemura M (2000) Studies on 8-methoxyquinolones: synthesis and antibacterial activity of 7-(3-amino-4-substituted)pyrrolidinyl derivatives. Chem Pharm Bull 48: 1667–72

    CAS  Google Scholar 

  35. Hayashi N, Amano H, Ohshita Y, Niino Y, Yoshida J, Yazaki A (1996) In vitro and in vivo activities, pharmacokinetics and toxicity of WQ-2756 and WQ-2765, two novel fluoroquinolones. 36th Interscience Conference on Antimicrobial Agents and Chemotherapy. New Orleans. Abstr. F051

    Google Scholar 

  36. Amano H, Hayashi N, Ohshita Y, Niino Y, Yazaki A (1997) WQ-2724 and WQ-2743, novel fluoroquinolones: in vitro and in vivo activities, pharmacokinetics and toxicity. 37th Interscience Conference on Antimicrobial Agents and Chemotherapy, Toronto. Abstr. F163

    Google Scholar 

  37. Hayashi N, Ohshita Y, Amano H, Hirao Y, Niino Y, Yazaki A (1999) WQ-3330 and WQ-2942, structure-activity relationships of novel 8-methyl quinolones containing an aminophenyl group at the N1-position. 39th Interscience Conference on Antimicrobial Agents and Chemotherapy. San Francisco. Abstr. F557

    Google Scholar 

  38. Hayashi N, Hashimoto K, Yazaki A (2001) A novel substituent at the 1-position markedly decreases the phototoxicity of an 8-chloro fluoroquinolone, WQ-2756, in vivo and in vitro. 41st Interscience Conference on Antimicrobial Agents and Chemotherapy. Chicago. Abstr. F556

    Google Scholar 

  39. Jung J-C, Jung Y-J, Park O-S (2001) Synthesis of 4-hydroxyquinolone-2(1H)-one analogues and 2-substituted quinolone derivatives. J Heterocyclic Chem 38: 61–67

    CAS  Google Scholar 

  40. Matsuoka M, Segawa J, Amimoto I, Masui Y, Tomii Y, Kitano M, Kise M (1999) Synthesis and antibacterial activity of novel 7-substituted-6-fluoro-l-fluoromethyl-4-xox-4H-[1, 3]-thiazeto[3, 2-a]quinoline-3-carboxylic acid derivatives. Chem Phar Bull 47: 1765–1773

    CAS  Google Scholar 

  41. Matsuoka M, Segawa J, Amimoto I, Masui Y, Tomii Y, Kitano M, Kise M (1999) Synthesis and antibacterial activity of novel 7-substituted-6-fluoro-l-methylene-4-xox-4H-[1, 3]-thiazeto[3, 2-a]quinoline-3-carboxylic acid derivatives. Heterocycl 51: 2915–2930

    CAS  Google Scholar 

  42. Cecchetti V, Fravolini A, Lorenzini MC, Tabarrini O, Terni P, Xin T (1996) Studies on 6-aminoquinolones: synthesis and antibacterial evaluation of 6-amino-8-methylquinolones. J Med Chem 39: 436–445

    CAS  PubMed  Google Scholar 

  43. Hong CY, Kim SH, Kim YK (1997) Novel 5-amino-6-methylquinolone antibacterials: a new class of non-6-fluoroquinolones. Bioorg Med Chem Lett 7: 1875–1878

    CAS  Google Scholar 

  44. Gootz TD, McGuirk PR, Moynihan MS, Haskell SL (1994) Placement of alkyl substituents on the c-7 piperizine ring of fluoroquinolones: dramatic differential effects on mammalian topoisomerase II and DNA gyrase. Antimicrob Agents Chemother 38: 130–133

    CAS  PubMed  PubMed Central  Google Scholar 

  45. Renau TE, Sanchez JP, Gage JW, Dever JA, Shapiro MA, Gracheck SJ, Domagala JM (1996) Structure-activity relationships of the quinolone antibacterial against mycobacteria: effect of structural changes at the N-1 and C-7. J Med Chem 39: 729–735

    CAS  PubMed  Google Scholar 

  46. Hong CY, Kim YK, Chang JH, Kim SH, Choi H, Nam H, Kim YZ, Kwak JH (1997) Novel fluoroquinolone antibacterial agents containing oxime-substituted (aminomethyl)pyrrolidines: synthesis and antibacterial activity of 7-(4-(aminomethyl)-3-(methoxyimino)pyrrolidin-1-yl)-1-cyclo-propyl-6-fluoro-4-oxo-l,4-dihydro[1, 8]naphthyridine-3-carboxylic acid (LB20304). J Med Chem 40: 3584–3593

    CAS  PubMed  Google Scholar 

  47. Fujita M, Chiba K, Tominaga Y, Hino K (1998) 7-(2-Aminomethyl-l-azetidinyl)-4-oxoquinoline-3-carboxylic acids as potent antibacterial agents: design, synthesis, and antibacterial activity. Chem Pharm Bull 46: 787–796

    CAS  Google Scholar 

  48. Haramura M, Okamachi A, Makino T, Kohda A, Katoh Y, Munemura K, Ito T, Matsumoto M, Kojima K, Yokota T (1994) Synthesis and biological activity of new 8-methoxyquinolones possessing 7-aminoalkyl group. 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Orlando. Abstr. F36

    Google Scholar 

  49. Fujita M, Chiba K, Nakano J, Tominaga Y, Matsumoto J (1998) Synthesis and structure-antibacterial activity relationships of 7-(3-amino-l-propyl and 3-amino-1-propyl)quinolones. Chem Pharm Bull 46: 631–638

    CAS  Google Scholar 

  50. Renau TE, Gage JW, Dever JA, Roland GE, Joannides ET, Shapira MA, Sanchez JP, Gracheck SJ, Domagala JM, Jacobs MR, Reynolds RC (1996) Structure-activity relationships of quinolone agents against mycobacteria: effect of structural modification at the 8 position. Antimicrob Agents Chemother 40: 2363–2368

    CAS  PubMed  PubMed Central  Google Scholar 

  51. Sanchez JP, Gogliotti RD, Domagala JM, Gracheck SJ, Huband MD, Sesnie JA, Cohen MA, Shapiro MA (1995) The synthesis, structure-activity, and structure-side effect relationships of a series of 8-alkoxy-and 5-amino-8-alkoxyquinolone antibacterial agents. J Med Chem 38: 4478–4487

    CAS  PubMed  Google Scholar 

  52. Kitani H, Kurada T, Moriguchi A, An H, Hirayama F, Ikeda Y, Kawakita T (1997) Synthesis and structural optimization of 7-(3,3-disubstituted-l-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acids as antibacterial agents. Bioorg Med Chem Lett 7:515–520

    CAS  Google Scholar 

  53. Hong CY, Kim YK, Chang JH, Kim SH, Choi H, Nam H, Kim YZ, Kwak H (1997) Novel fluoroquinolone antibacterial agents containing oxime-substituted (aminomethyl)pyrrolidines: synthesis and antibacterial activity of 7-(4-(aminomethyl)-3-(methoxyimino)pyrrolidine-l-yl)-1-cyclopropyl-6-fluoro-4-oxo-l,4-dihydro[1, 8]naphthyridine-3-carboxylic acid (LB20304). J Med Chem 40: 3584–3593

    CAS  PubMed  Google Scholar 

  54. Hong CY, Kim YK, Lee YH, Kwak JH (1998) Methyloxime-substituted aminopyrrolidine: a new surrogate for 7-basic group of quinolone. Bioorg Med Chem Lett 8: 221–226

    CAS  PubMed  Google Scholar 

  55. Cecchetti V, Tabarrini O, Sabatini S, Miao H, Filipponi E, Fravolini A (1999) Studies on 6-aminoquinolones: synthesis and antibacterial evaluation of 6-amino-8-ethyl-and 6-amino-8methoxyquinolones. Bioorg Med Chem Lett 7: 2465–2471

    CAS  Google Scholar 

  56. Li Q, Mitscher LA, Shen LL (2000) The 2-pyridone antibacterial agents. Med Res Rev 20: 231–293

    CAS  PubMed  Google Scholar 

  57. Li Q, Chu DTW, Claiborne A, Cooper CS, Lee CM, Raye K, Berst KB, Donner P et al (1996) Synthesis and structure-activity relationships of 2-pyridones: A novel series of potent DNA gyrase inhibitors as antibacterial agents. J Med Chem 39: 3070–3088

    CAS  PubMed  Google Scholar 

  58. Shen LL, Tanaka SK, Chu DTW (1997) Quinolones, 2-pyridones and resistant type II DNA topoisomerases. Current Pharmaceutical Design 3: 169–176

    CAS  Google Scholar 

  59. Saiki AYC, Shen LL, Chen CM, Baranowski J, Lerner CG (1999) DNA Cleavage activities of Staphlococcus aureus gyrase and topoisomerase IV stimulated by quinolones and 2-pyridones. Antimicrob Agents Chemother 43: 1574–1577

    CAS  PubMed  PubMed Central  Google Scholar 

  60. Klein LL, DeGoey DA, Thomas SA, Yeung CM, Leone CL, Grampovnik DJ, Chu DT, Lartey PA (1997) Preparation and antibacterial activity of pyridopyridone analogs: C-1 modifications. Bioorg Med Chem Lett 7: 1167–1170

    CAS  Google Scholar 

  61. Ma Z, Chu DTW, Cooper CS, Li Q, Fung AKL, Wang S, Shen LL, Flamm RK, Nilius AM, Alder JD, Meulbroek JA, Or YS (1999) Synthesis and antimicrobial activity of 4H-4-oxoquinolizine derivatives: Consequences of structural modification at the C-8 position. J Med Chem 42: 4202–4213

    CAS  PubMed  Google Scholar 

  62. Cecchetti V, Fravolini A, Palumbo M, Sissi C, Tabarrini O (1996) Potent 6-desfluoro-8methylquinolones as new lead compounds in antibacterial chemotherapy. J Med Chem 39: 4952–4957

    CAS  PubMed  Google Scholar 

  63. Takahata M, Mitsuyama J, Yamashiro Y, Yonezawa M, Araki H, Todo Y, Minami S, Watanabe Y, Narita H (1999) In vitro and in vivo antimicrobial activities of t-3811me, a novel des-f(6)quinolone. Antimicrob Agents Chemother 43: 1077–1084

    CAS  PubMed  PubMed Central  Google Scholar 

  64. Nagai A, Takahata M, Miyazaki M, Kawamura Y, Kodama T, Todo Y, Watanabe Y, Narita H (1997) T-3811, a novel des-f(6)-quinolone: toxicological evaluation. In: Abstracts of the 37th ICAAC, Toronto Abstract F-162, p.173. American Society for Microbiology, Washington, DC

    Google Scholar 

  65. Murphy VA, Ledoussal B, Renick PJ, Twinem TL, Morris TW (2001) Clastogenicity and human topoisomerase II inhibition profiles of non-fluorinated quinolones (NFQs). 41st Interscience Conference on Antimicrobial Agents and Chemotherapy, Chicago. Abstr. F563

    Google Scholar 

  66. Roychoudhury S, Twinem TL, Makin KM, McIntosh EJ, Ledoussal B, Catrenich CE (2001) Activity of non-fluorinated quinolones (NFQs) against quinolone-resistant Escherichia coli and Streptococcus pneumoniae. JAntimicrob Chemother 48: 29–36

    CAS  Google Scholar 

  67. Roychoudhury S, Catrenich CE, McIntosh EJ, McKeever HD, Makin KM, Koenigs PM, Ledoussal B (2001) Quinolone resistance in staphylococci: activities of new nonfluorinated quinolones against molecular targets in whole cells and clinical isolates. Antimicrob Agents Chemother 45: 1115–1120

    CAS  PubMed  PubMed Central  Google Scholar 

  68. Ledoussal B, Almstead JK, Gallagher CP, Gray JL, Hu XE, Kim NK, Mckeever HD, Taylor CJ, Twinem TL (2001) New 7-piperidinyl non-fluorinated quinolones (NFQs), synthesis and structure-activity relationships. 41st Interscience Conference on Antimicrobial Agents and Chemotherapy, Chicago. Abstr. F564

    Google Scholar 

  69. Takahata M, Mitsuyama J, Yamashiro Y, Yonezawa M, Araki H, Todo Y, Minami S, Watanabe Y, Narita H (1999) In vitro and in vivo antimicrobial activities of T-3811ME, a novel des-F(6)quinolone. Antimicrob Agents Chemother 43: 1077–1084

    CAS  PubMed  PubMed Central  Google Scholar 

  70. Lawrence LE, Wu P, Fan L, Gouveia KE, Card A, Casperson M, Denbleyker K, Barrett JF (2001) The inhibition and selectivity of bacterial topoisomerases by BMS-284756 and its analogues. J Antimicrob Chemother 48: 195–201

    CAS  PubMed  Google Scholar 

  71. Hayashi K, Todo Y, Hamamoto S, Ojima K, Yamada M, Kito T, Takahata M, Watanabe Y, Narita H (1997) T-3811, a novel des-F(6)-quinolones: synthesis and in vitro activity of 7-(isoindolin-5yl) derivatives. 37th Interscience Conference on Antimicrobial Agents and Chemotherapy, Toronto. Abstr. F158

    Google Scholar 

  72. Tabart M, Picaut G, Berthaud N, Desconclois J-F (2000) Synthesis and biological evaluation of RP60556A, a new tropical antibacterial agent. 40th Interscience Conference on Antimicrobial Agents and Chemotherapy, Toronto. Abstr. 1512

    Google Scholar 

  73. Berthaud N, Dutka-Malen S, Boisrobert V, Efremenko F, Gouin A-M, Martin J, Rousseau J, Desnottes J-F (2000) RP60556A, a new tropical benzonaphthyridone derivative: in vitro bacteriostatic activity against Gram-positive cocci resistant to quinolones. 40th Interscience Conference on Antimicrobial Agents and Chemotherapy, Toronto, Abstr. 1514

    Google Scholar 

  74. Sraga J, Guerry P, Kompis I (1994) Synthesis and biological activity of tetrahydropyrido[2’, 3’: 4, 5]imidazo[1, 2-clpyrimidine-6,8-diones. Heiv Chim Acta 77: 1057–1064

    CAS  Google Scholar 

  75. Cecchetti V, Fravolini A, Sabatini S, Tabarrini O, Xin T (1998) Dibenzo[1, 6]naphthyridiones as modified quinolone antibacterials. Eur J Med Chem 33: 899–903

    CAS  Google Scholar 

  76. Tabarrini O, Cecchetti V, Fravolini A, Nocentini G, Barzi A, Sabatini S, Miao H, Sissi C (1999) Design and synthesis of modified quinolones as antitumoral acridones. J Med Chem 42: 2136–2144

    CAS  PubMed  Google Scholar 

  77. Sui Z, Altom J, Nguyen VN, Fernandez J, Bernstein JI, Hiliard JJ, Barrett JF, Podlogar BL, Ohemeng KA (1998) Synthesis and inhibitory activity of novel tri-and tetracyclic quinolines against topoisomerases. Bioorg Med Chem 6: 735–742

    CAS  PubMed  Google Scholar 

  78. Fujita M, Egawa H, Miyamoto T, Nakano J, Matsumoto J (1996) Pyrroloquinolones and pyrrazoloquinolones as potential antibacterial agents. synthesis and antibacterial activity. Eur J Med Chem 31: 981–988

    CAS  Google Scholar 

  79. Abdelal AM, Gineinah MM, Kheira MM (1999) Synthesis and antibacterial activity of 2-[4-(4-fluorophenyl)piperizin-l-yl]-4-substituted-4,7-dihydro-7-oxo-1,2,4-triazolo[1, 5-a]pyrimidine-6carboxylic acids and its analogs. Med Chem Res 9: 277–290

    CAS  Google Scholar 

  80. Chung S-K, Lee JW, Shim NY, Kwon TW (1996) p-Quinone methides as geometric analogues of quinolone carboxylate antibacterials. Bioorg Med Chem Lett 6: 1309–1312

    CAS  Google Scholar 

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Authors and Affiliations

  1. Medicinal Chemistry Department, Kansas University, 4010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, KS, 66045-7582, USA

    Lester A. Mitscher

  2. Cumbre Inc., 1502 Viceroy Drive, Dallas, TX, 75235-2304, USA

    Zhenkun Ma

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  1. Lester A. Mitscher
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  2. Zhenkun Ma
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Editors and Affiliations

  1. Faculty of Medicine, The University of Manitoba, 409 Tacho Avenue, Winnipeg, Manitoba, R2H 2A6, Canada

    Allan R. Ronald

  2. Microbiology Laboratory, Mt. Sinai Hospital, 600 University Avenue, Toronto, Ontario, M5G 1X5, Canada

    Donald E. Low

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Mitscher, L.A., Ma, Z. (2003). Structure-activity relationships of quinolones. In: Ronald, A.R., Low, D.E. (eds) Fluoroquinolone Antibiotics. Milestones in Drug Therapy. Birkhäuser, Basel. https://doi.org/10.1007/978-3-0348-8103-6_2

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  • DOI: https://doi.org/10.1007/978-3-0348-8103-6_2

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