Effect of N-1/C-8 ring fusion and C-7 ring structure on fluoroquinolone lethality

Antimicrobial Agents and Chemotherapy

Volumn 54, Issue 12, 2010, Pages 5214-5221

  Malik, Muhammad ^b   Marks, Kevin R ^a   Schwanz, Heidi A ^a   German, Nadezhda ^a   Drlica, Karl ^b,c   Kerns, Robert J ^a  

^a UNIVERSITY OF IOWA   (United States)

^b PUBLIC HEALTH RESEARCH INSTITUTE   (United States)

^c RUTGERS NEW JERSEY MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 CYCLOPROPYL 6 FLUORO 1,4 DIHYDRO 8 METHOXY 4 OXO 7 (1 PIPERAZINYL) 3 QUINOLINECARBOXYLIC ACID; 1 CYCLOPROPYL 7 (3 ETHYL 1 PIPERAZINYL) 6 FLUORO 1,4 DIHYDRO 8 METHOXY 4 OXO 3 QUINOLINECARBOXYLIC ACID; 1 CYCLOPROPYL 7 (4 ETHYL 1 PIPERAZINYL) 6 FLUORO 1,4 DIHYDRO 8 METHOXY 4 OXO 3 QUINOLINECARBOXYLIC ACID; CHLORAMPHENICOL; GATIFLOXACIN; LEVOFLOXACIN; MARBOFLOXACIN; MOXIFLOXACIN; PAZUFLOXACIN; QUINOLINE DERIVED ANTIINFECTIVE AGENT; RUFLOXACIN; UIKRM 1025; UIKRM 1029; UIKRM 1033; UING 4255; UING 4257; UNCLASSIFIED DRUG;

ARTICLE; BACTERICIDAL ACTIVITY; BACTERIOSTASIS; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG BINDING; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR INTERACTION; NONHUMAN; PRIORITY JOURNAL; PROTEIN SYNTHESIS; STEREOSPECIFICITY;

ANTI-INFECTIVE AGENTS; CHLORAMPHENICOL; ESCHERICHIA COLI; FLUOROQUINOLONES; OFLOXACIN; OXAZINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78649644723     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.01054-10     Document Type: Article

References (27)

1. Burkhardt, O., and T. Welte. 2009. 10 years' experience with the pneumococcal quinolone moxifloxacin. Expert Rev. Anti Infect. Ther. 7:645-668.
2. Chen, C.-R., M. Malik, M. Snyder, and K. Drlica. 1996. DNA gyrase and topoisomerase IV on the bacterial chromosome: quinolone-induced DNA cleavage. J. Mol. Biol. 258:627-637.
3. Deitz, W. H., T. M. Cook, and W. A. Goss. 1966. Mechanism of action of nalidixic acid on Escherichia coli. III. Conditions required for lethality. J. Bacteriol. 91:768-773.
4. Drlica, K., H. Hiasa, R. Kerns, M. Malik, A. Mustaev, and X. Zhao. 2009. Quinolones: action and resistance updated. Curr. Top. Med. Chem. 9:981-998.
5. Goss, W., W. Deitz, and T. Cook. 1965. Mechanism of action of nalidixic acid on Escherichia coli. II. Inhibition of deoxyribonucleic acid synthesis. J. Bacteriol. 89:1068-1074.
6. Howard, B. M., R. J. Pinney, and J. T. Smith. 1993. 4-Quinolone bactericidal mechanisms. Arzneimittelforschung 43:1125-1129.
7. Ito, T., M. Matsumoto, and T. Nishino. 1995. Improved bactericidal activity of Q-35 against quinolone-resistant staphylococci. Antimicrob. Agents Chemother. 39:1522-1525.
8. Kampranis, S. C., and A. Maxwell. 1998. The DNA gyrase-quinolone complex, ATP hydrolysis and the mechanism of DNA cleavage. J. Biol. Chem. 273:22615-22626.
9. Kuramoto, Y., Y. Ohshita, J. Yoshida, A. Yazaki, M. Shiro, and T. Koike. 2003. A novel antibacterial 8-chloroquinolone with a distorted orientation of the N-1-(5-amino-2.4-difluorophenyl) group. J. Med. Chem. 46:1905-1917.
10. Lamb, E. 1 May 2008 posting date. Top 200 prescription drugs of 2007. Pharm. Times. http://www.pharmacytimes.com/issue/pharmacy/2008/2008-05/2008-05- 8520.
11. Laponogov, I., M. Sohi, D. Veselkov, X. Pan, R. Sawhney, A. Thompson, K. McAuley, L. Fisher, and M. Sanderson. 2009. Structural insight into the quinolone-DNA cleavage complex of type IIA topoisomerases. Nat. Struct. Mol. Biol. 16:667-669.
12. Lewin, C. S., and S. G. B. Amyes. 1989. The bactericidal activity of R-3355, an optically active isomer of ofloxacin. J. Med. Microbiol. 30:227-231.
13. Lewin, C. S., and S. G. B. Amyes. 1990. Conditions required for the bactericidal activity of fleroxacin and pefloxacin against Escherichia coli KL16. J. Med. Microbiol. 32:83-86.
14. Lewin, C. S., S. G. B. Amyes, and J. T. Smith. 1989. Bactericidal activity of enoxacin and lomefloxacin against Escherichia coli KL16. Eur. J. Clin. Microbiol. Infect. Dis. 8:731-733.
15. Louie, A., H. Heine, K. Kim, D. Brown, B. VanScoy, W. Liu, M. Kinzig-Schippers, F. Sörgel, and G. Drusano. 2008. Use of an in vitro pharmacodynamic model to derive a linezolid regimen that optimizes bacterial kill and prevents emergence of resistance in Bacillus anthracis. Antimicrob. Agents Chemother. 52:2486-2496.
16. Malik, M., and K. Drlica. 2006. Moxifloxacin lethality with Mycobacterium tuberculosis in the presence and absence of chloramphenicol. Antimicrob. Agents Chemother. 50:2842-2844.
17. Malik, M., G. Hoatam, K. Chavda, R. Kerns, and K. Drlica. 2010. Novel approach for comparing quinolones for emergence of resistant mutants during quinolone exposure. Antimicrob. Agents Chemother. 54:149-156.
18. Malik, M., S. Hussain, and K. Drlica. 2007. Effect of anaerobic growth on quinolone lethality with Escherichia coli. Antimicrob. Agents Chemother. 51:28-34.
19. Malik, M., T. Lu, X. Zhao, A. Singh, C. Hattan, J. Domagala, R. Kerns, and K. Drlica. 2005. Lethality of quinolones against Mycobacterium smegmatis in the presence or absence of chloramphenicol. Antimicrob. Agents Chemother. 49:2008-2014.
20. Malik, M., X. Zhao, and K. Drlica. 2006. Lethal fragmentation of bacterial chromosomes mediated by DNA gyrase and quinolones. Mol. Microbiol. 61:810-825.
21. Manes, S. H., G. J. Pruss, and K. Drlica. 1983. Inhibition of RNA synthesis by oxolinic acid is unrelated to average DNA supercoiling. J. Bacteriol. 155:420-423.
22. Miller, J. 1972. Experiments in molecular genetics. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
23. Pohlhaus, J., and K. N. Kreuzer. 2005. Norfloxacin-induced DNA gyrase cleavage complexes block Escherichia coli replication forks, causing double-stranded breaks in vivo. Mol. Microbiol. 56:1416-1429.
24. Sternglanz, R., S. DiNardo, K. A. Voelkel, Y. Nishimura, Y. Hirota, A. K. Becherer, L. Zumstein, and J. C. Wang. 1981. Mutations in the gene coding for Escherichia coli DNA topoisomerase I affecting transcription and transposition. Proc. Natl. Acad. Sci. U. S. A. 78:2747-2751.
25. Wang, X., X. Zhao, M. Malik, and K. Drlica. 2010. Contribution of reactive oxygen species to pathways of quinolone-mediated bacterial cell death. J. Antimicrob. Chemother. 65:520-524.
26. Wohlkonig, A., P. F. Chan, A. P. Fosberry, P. Homes, J. Huang, M. Kranz, V. R. Leydon, T. J. Miles, N. D. Pearson, R. L. Perera, A. J. Shillings, M. N. Gwynn, and B. D. Bax. 2010. Structural basis of quinolone inhibition of type IIA topoisomerases and target-mediated resistance. Nat. Struct. Mol. Biol. 17:1152-1153.
27. 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.