Contributions of the 8-methoxy group of gatifloxacin to resistance selectivity, target preference, and antibacterial activity against Streptococcus pneumoniae

Antimicrobial Agents and Chemotherapy

Volumn 45, Issue 6, 2001, Pages 1649-1653

  Fukuda, Hideyuki ^a   Kishii, Ryuta ^a   Takei, Masaya ^a   Hosaka, Masaki ^a  

^a KYORIN PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CIPROFLOXACIN; GATIFLOXACIN;

ANTIBACTERIAL ACTIVITY; ARTICLE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; STREPTOCOCCUS INFECTION; STREPTOCOCCUS PNEUMONIAE; STRUCTURE ACTIVITY RELATION;

ANTI-INFECTIVE AGENTS; DNA GYRASE; DNA TOPOISOMERASE IV; DNA TOPOISOMERASES, TYPE II; DRUG RESISTANCE, MICROBIAL; FLUOROQUINOLONES; MICROBIAL SENSITIVITY TESTS; MUTATION; STREPTOCOCCUS PNEUMONIAE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035023593     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.45.6.1649-1653.2001     Document Type: Article

References (39)

1. Akasaka, T., S. Kurosaka, Y. Uchida, M. Tanaka, K. Sato, and I. Hayakawa. 1998. Antibacterial activities and inhibitory effects of sitafloxacin (DU-6859a) and its optical isomers against type II topoisomerases. Antimicrob. Agents Chemother. 42:1284-1287.
2. Alovero, F. L., X.-S. Pan, J. E. Morris, R. H. Manzo, and L. M. Fisher. 2000. Engineering the specificity of antibacterial fluoroquinolones: benzenesulfonamide modifications at C-7 of ciprofloxacin change its primary target in Streptococcus pneumoniae from topoisomerase IV to gyrase. Antimicrob. Agents Chemother. 44:320-325.
3. Balas, D., E. Fernández-Moreira, and A. G. De La Campa. 1998. Molecular characterization of the gene encoding the DNA gyrase A subunit of Streptococcus pneumoniae. J. Bacteriol. 180:2854-2861.
4. Beyer, R., E. Pestova, J. J. Millichap, V. Stosor, G. A. Noskin, and L. R. Peterson. 2000. A convenient assay for estimating the possible involvement of efflux of fluoroquinolones by Streptococcus pneumoniae and Staphylococcus aureus: evidence for diminished moxifloxacin, sparfloxacin, and trovafloxacin efflux. Antimicrob. Agents Chemother. 44:798-801.
5. Dong, Y., C. Xu, X. Zhao, J. Domagala, and K. Drlica. 1998. Fluoroquinolone action against mycobacteria: effects of C-8 substituents on growth. survival, and resistance. Antimicrob. Agents Chemother. 42:2978-2984.
6. Fu, K. P., S. C. Lafredo, B. Foleno, D. M. Isaacson, J. F. Barrett, A. J. Tobia, and M. E. Rosenthale. 1992. In vitro and in vivo antibacterial activities of levofloxacin (l-ofloxacin), an optically active ofloxacin. Antimicrob. Agents Chemother. 36:860-866.
7. Fukuda, H., S. Hori, and K. Hiramatsu. 1998. Antibacterial activity of gatifloxacin (AM-1155, CG5501, BMS-206584), a newly developed fluoroquinolone, against sequentially acquired quinolone-resistant mutants and the norA transformant of Staphylloccus aureus. Antimicrob. Agents Chemother. 42:1917-1922.
8. Fukuda, H., and K. Hiramatsu. 1999. Primary targets of fluoroquinolones in Streptococcus pneumoniae. Antimicrob. Agents Chemother. 43:410-412.
9. Fukuda, H. 2000. Genetic study of the mechanisms of action of fluoroquinolones in Streptococcus pneumoniae. Jpn. J. Chemother. 48:243-250.
10. Gill, M. N., N. P. Brenwald, and R. Wise. 1999. Identification of efflux pump gene, pmrA, associated with fluoroquinolone resistance in Streptococcus pneumoniae. Antimicrob. Agents Chemother. 43:187-189.
11. Gootz, T. D., R. Zaniewski, S. Haskell, B. Schmieder, J. Tankovic, D. Girard, P. Courvalin, and R. J. Polzer. 1996. Activity of the new fluoroquinolone trovafloxacin (CP-99, 219) against DNA gyrase and topoisomerase IV mutants of Streptococcus pneumoniae selected in vitro. Antimicrob. Agents Chemother. 40:2691-2697.
12. Hosaka, M., T. Yasue, H. Fukuda, H. Tomizawa, H. Aoyama, and K. Hirai. 1992. In vitro and in vivo antibacterial activities of AM-1155, a new 6-fluoro-8-methoxy quinolone. Antimicrob. Agents Chemother. 36:2108-2117.
13. Ince, D., and D. C. Hooper. 2000. Mechanisms and frequency of resistance to premafloxacin in Staphylococcus aureus: novel mutations suggest novel drug-target interactions. Antimicrob. Agents Chemother. 44:3344-3350.
14. Ito, T., M. Matsumoto, and T. Nishino. 1995. Improved bactericidal activity of Q-35 against quinolone-resistant staphylococci. Antimicrob. Agents Chemother. 39:1522-1525.
15. Jones, M. E., D. F. Sahm, N. Martin, S. Scheuring, P. Heisig, C. Thornsberry, K. Köhrer, and F.-J. Schmitz. 2000. Prevalence of gyrA, gyrB, parC, and parE mutations in clinical isolates of Streptococcus pneumoniae with decreased susceptibilities to different fluoroquinolones and originating from worldwide surveillance studies during the 1997-1998 respiratory season. Antimicrob. Agents Chemother. 44:462-466.
16. Junior, C., V. Keller, M.-D. Kitzis, N. J. Moreau, and L. Gutmann. 1996. High-level fluoroquinolone resistance in Streptococcus pneumoniae requires mutations in parC and gyrA. Antimicrob. Agents Chemother. 40:2760-2764.
17. Lu, T., X. Zhao, and K. Drlica. 1999. Gatifloxacin activity against quinolone-resistant gyrase: allele-specific enhancement of bacteriostatic and bactericidal activities by the C-8-methoxy group. Antimicrob. Agents Chemother. 43:2969-2974.
18. Markham, P. N. 1999. Inhibition of the emergence of ciprofloxacin resistance in Streptococcus pneumoniae by the multidrug efflux inhibitor reserpine. Antimicrob. Agents Chemother. 43:988-989.
19. Muñoz, R., and A. G. De la Campa. 1996. ParC subunit of DNA topoisomerase IV of Streptococcus pneumoniae is a primary target of quinolones and cooperates with DNA gyrase A subunit in forming resistant phenotype. Antimicrob. Agents Chemother. 40:2252-2257.
20. Nakamura, S., A. Minami, K. Nakata, N. Kurobe, K. Kouno, Y. Sakaguchi, S. Kashimoto, H. Yoshida, T. Kojima, T. Ohue, K. Fujimoto, M. Nakamura, M. Hashimoto, and M. Shimizu. 1989. In vitro and in vivo antibacterial activities of AT-4140, a new broad-spectrum quinolone. Antimicrob. Agents Chemother. 33:1167-1173.
21. Neu, H. C., A. Novelli, and N.-X. Chin. 1989. Comparative in vitro activity of a new quinolone, AM-1091. Antimicrob. Agents Chemother. 33:1036-1041.
22. Onodera, Y., Y. Uchida, M. Tanaka, and K. Sato. 1999. Dual inhibitory activity of sitafloxacin (DU-6859a) against DNA gyrase and topoisomerase IV of Streptococcus pneumoniae. J. Antimicrob. Chemother. 44:533-536.
23. Pan, X.-S., and L. M. Fisher. 1998. DNA gyrase and topoisomerase IV are dual targets of clinafloxacin action in Streptococcus pneumoniae. Antimicrob. Agents Chemother. 42:2810-2816.
24. Pan, X.-S., J. Ambler, S. Mehter, and L. M. Fisher. 1996. Involvement of topoisomerase IV and DNA gyrase as ciprofloxacin targets in Streptococcus pneumoniae. Antimicrob. Agents Chemother. 40:2321-2326.
25. Pan, X.-S., and L. M. Fisher. 1996. Cloning and characterization of the parC and parE genes of Streptococcus pneumoniae encoding DNA topoisomerase IV: role in fluoroquinolone resistance. J. Bacteriol. 178:4060-4069.
26. Pan, X.-S., and L. M. Fisher. 1997. Targeting of DNA gyrase in Streptococcus pneumoniae by sparfloxacin: selective targeting of gyrase or topoisomerase IV by quinolones. Antimicrob. Agents Chemother. 41:471-474.
27. Pan, X.-S., and L. M. Fisher. 1999. Streptococcus pneumoniae DNA gyrase and topoisomerase IV: overexpression, purification, and differential inhibition by fluoroquinolones. Antimicrob. Agents Chemother. 43:1129-1136.
28. Pestova, E., J. J. Millichap, G. A. Noskin, and L. R. Peterson. 2000. Intracellular targets of moxifloxacin: a comparison with other fluoroquinolones. J. Antimicrob. Chemother. 45:583-590.
29. Renau, T. E., J. W. Gage, J. A. Dever, G. E. Roland, E. T. Joannides, M. A. Shapiro, J. P. Sanchez, S. J. Gracheck, J. M. Domagala, M. R. Jacobs, and R. C. Reynolds. 1996. Structure-activity relationships of quinolone agents against mycobacteria: effect of structural modifications at the 8 position. Antimicrob. Agents Chemother. 40:2363-2368.
30. Tankovic, J., B. Perichon, J. Duval, and P. Courvalin. 1946. Contribution of mutations in gyrA and parC genes to fluoroquinolone resistance of mutants of Streptococcus pneumoniae obtained in vivo and in vitro. Antimicrob. Agents Chemother. 40:2502-2510.
31. Tsurumaki, Y., H. Manda, M. Takei, and M. Hosaka. 2000. In vitro antimicrobial activity of gatifloxacin against 873 clinical isolates from respiratory tract, urinary tract and surgical infections during 1997-1998 in Japan. J. Antimicrob. Chemother. 45:685-684.
32. Varon, E., C. Janoir, M.-D. Kitzis, and L. Gutmann. 1999. ParC and GyrA may be interchangeable initial targets of some fluoroquinolones in Streptococcus pneumoniae. Antimicrob. Agents Chemother. 43:302-306.
33. Wakebe, H., T. Imada, H. Yoneda, F. Mukai, K. Ohguro, K. Ohmori, H. Tamaoka, and Y. Yabuuchi. 1994. Evaluation of OPC-17116 against important pathogens that cause respiratory tract infections. Antimicrob. Agents Chemother. 38:2340-2345.
34. Woodcock, J. M., J. M. Andrews, F. J. Boswell, N. P. Brenwald, and R. Wise. 1997. In vitro activity of BAY 12-8039, a new fluoroquinolone. Antimicrob. Agents Chemother. 41:101-106.
35. Yoshida, H., M. Bogaki, M. Nakamura, and S. Nakamura. 1990. Quinolone resistance determining region in the DNA gyrase gyrA gene of Escherichia coli. Antimicrob. Agents Chemother. 34:1271-1272.
36. Yoshida, H., M. Bogaki, M. Nakamura, L. M. Yamanaka, and S. Nakamura. 1991. Ouinolone resistance-determining region in the DNA gyrase gyrB gene of Echerichia coli. Antimicrob. Agents Chemother. 35:1647-1650.
37. Zhao B. Y., R. Pine, J. Domagala, and K. Drlica. 1999. Fluoroquinolone action against clinical isolates of Mycobacterium tuberculosis: effects of a C-8 methoxyl group on survival in liquid media and in human macrophages. Antimicrob. Agents Chemother. 43:661-666.
38. Zhao, X., C. Xu, J. Domagala, and K. Drlica. 1997. DNA topoisomerase target of the fluoroquinolones: a strategy for avoiding bacterial resistance. Proc. Natl. Acad. Sci. USA 94:13991-13996.
39. Zhao, X., J.-Y. Wang, C. Xu, Y. Dong, J. Zhou, J. Domagala, and K. Drlica. 1998. Killing of Staphylococcus aureus by C-8-methoxy fluoroquinolones. Antimicrob. Agents Chemother. 42:956-958.