Fluoroquinolone and quinazolinedione activities against wild-type and gyrase mutant strains of Mycobacterium smegmatis

Antimicrobial Agents and Chemotherapy

Volumn 55, Issue 5, 2011, Pages 2335-2343

  Malik, Muhammad ^a   Marks, Kevin R ^c   Mustaev, Arkady ^a,b   Zhao, Xilin ^a,b   Chavda, Kalyan ^a   Kerns, Robert J ^c   Drlica, Karl ^a,b  

^a PUBLIC HEALTH RESEARCH INSTITUTE   (United States)

^b RUTGERS NEW JERSEY MEDICAL SCHOOL   (United States)

^c UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORAMPHENICOL; CIPROFLOXACIN; DNA TOPOISOMERASE (ATP HYDROLYSING); MOXIFLOXACIN; QUINAZOLINE DERIVATIVE; QUINOLONE DERIVATIVE;

ANTIBIOTIC SENSITIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; BACTERIOSTASIS; BACTERIUM MUTANT; COMPLEX FORMATION; CONTROLLED STUDY; DNA HELIX; DRUG UPTAKE; EFFUSION; LETHALITY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM SMEGMATIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN SYNTHESIS; STRUCTURE ACTIVITY RELATION; X RAY;

ANTI-BACTERIAL AGENTS; DNA GYRASE; FLUOROQUINOLONES; MICROBIAL SENSITIVITY TESTS; MUTATION; MYCOBACTERIUM SMEGMATIS; QUINAZOLINONES;

EID: 79955546959     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.00033-11     Document Type: Article

References (47)

1. Agrawal, D., Z. Udwadia, C. Rodriguez, and A. Mehta. 2009. Increasing incidence of fluoroquinolone-resistant Mycobacterium tuberculosis in Mumbai, India. Int. J. Tuberc. Lung Dis. 13:79-83.
2. Bax, B., et al. 2010. Type IIA topoisomerase inhibition by a new class of antibacterial agents. Nature 19:935-940.
3. Beylin, V., et al. 2007. The preparation of two, preclinical amino-quinazolinediones as antibacterial agents. Org. Process Res. Dev. 11:441-449.
4. Caminero, J., G. Sotgiu, A. Zumla, and G. Migliori. 2010. Best drug treatment for multidrug-resistant and extensively drug-resistant tuberculosis. Lancet Infect. Dis. 10:621-629.
5. 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.
6. Cole, S. T., et al. 1998. Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence. Nature 393:537-544. (Pubitemid 28319235)
7. Critchlow, S. E., and A. Maxwell. 1996. DNA cleavage is not required for the binding of quinolone drugs to the DNA gyrase-DNA complex. Biochemistry 35:7387-7393.
8. 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.
9. Dong, Y., X. Zhao, J. Domagala, and K. Drlica. 1999. Effect of fluoroquinolone concentration on selection of resistant mutants of Mycobacterium bovis BCG and Staphylococcus aureus. Antimicrob. Agents Chemother. 43:1756-1758.
10. Drlica, K., M. Malik, R. J. Kerns, and X. Zhao. 2008. Quinolone-mediated bacterial death. Antimicrob. Agents Chemother. 52:385-392.
11. Ellsworth, E., et al. 2006. 3-Aminoquinazolinediones as a new class of anti-bacterial agents demonstrating excellent antibacterial activity against wild-type and multidrug resistant organisms. J. Med. Chem. 49:6435-6438.
12. German, N., M. Malik, J. Rosen, K. Drlica, and R. Kerns. 2008. Use of gyrase resistance mutants to guide selection of 8-methoxy-quinazoline-2,4- diones. Antimicrob. Agents Chemother. 52:3915-3921.
13. Guillemin, I., V. Jarlier, and E. Cambau. 1998. Correlation between quinolone sensitivity patterns and sequences in the A and B subunits of DNA gyrase in mycobacteria. Antimicrob. Agents Chemother. 42:2084-2088.
14. Guillemin, I., et al. 1999. Purification and inhibition by quinolones of DNA gyrases from Mycobacterium avium, Mycobacterium smegmatis and Mycobacterium fortuitum bv. peregrinum. Microbiology 145:2527-2532. (Pubitemid 29454370)
15. Howard, B. M., R. J. Pinney, and J. T. Smith. 1993. 4-Quinolone bactericidal mechanisms. Arzneimittelforschung 43:1125-1129.
16. Huband, M. D., et al. 2007. In vitro and in vivo activities of PD 0305970 and PD 0326448, new bacterial gyrase/topoisomerase inhibitors with potent antibacterial activities versus multidrug-resistant gram-positive and fastidious organism groups. Antimicrob. Agents Chemother. 51:1191-1201.
17. Hutchings, K., et al. 2008. Synthesis and antibacterial activity of the C-7 side chain of 3-aminoquinazolinediones. Bioorg. Med. Chem. Lett. 18:5087-5090.
18. Jacobs, W. R., et al. 1991. Genetic systems in mycobacteria. Methods Enzymol. 204:537-555.
19. Kampranis, S., and A. Maxwell. 1998. The DNA gyrase-quinolone complex, ATP hydrolysis and the mechanism of DNA cleavage. J. Biol. Chem. 173: 22615-22626.
20. Kimura, Y., S. Atarashi, M. Takahashi, and I. Hayakawa. 1994. Synthesis and structure-activity-relationships of 7-[3-(1-aminoalkyl)pyrrolidinyl] quinolone and 7-[3-(1-aminocycloalkyl)pyrrolidinyl]quinolone antibacterials. Chem. Pharm. Bull. 42:1442-1454.
21. Laponogov, I., et al. 2010. Structural basis of gate-DNA breakage and resealing by type II topoisomerases. PLoS One 5:e11338.
22. Laponogov, I., et al. 2009. Structural insight into the quinolone-DNA cleavage complex of type IIA topoisomerases. Nat. Struct. Mol. Biol. 16:667-669.
23. Linder, J., E. Huang, M. Steinman, R. Gonzales, and R. Stafford. 2005. Fluoroquinolone prescribing in the United States: 1995 to 2002. Am. J. Med. 118:259-268. (Pubitemid 40312637)
24. Liu, Q., and J. Wang. 1998. Identification of active-site residues in the "GyrA" half of yeast DNA topoisomerase II. J. Biol. Chem. 273:20252-20260.
25. Lu, T., X. Zhao, and K. Drlica. 1999. Gatifloxacin activity against quinolone-resistant gyrase: allele-specific enhancement of bacteriostatic and bactericidal activity by the C-8-methoxy group. Antimicrob. Agents Chemother. 43:2969-2974.
26. Malik, M., and K. Drlica. 2006. Moxifloxacin lethality with Mycobacterium tuberculosis in the presence and absence of chloramphenicol. Antimicrob. Agents Chemother. 50:2842-2844.
27. Malik, M., G. Hoatam, K. Chavda, R. Kerns, and K. Drlica. 2010. Novel approach for comparing the abilities of quinolones to restrict the emergence of resistant mutants during quinolone exposure. Antimicrob. Agents Chemother. 54:149-156.
28. Malik, M., S. Hussain, and K. Drlica. 2007. Effect of anaerobic growth on quinolone lethality with Escherichia coli. Antimicrob. Agents Chemother. 51:28-34.
29. Malik, M., et al. 2005. Lethality of quinolones against Mycobacterium smegmatis in the presence or absence of chloramphenicol. Antimicrob. Agents Chemother. 49:2008-2014.
30. Malik, M., et al. 2010. Effect of N-1/c-8 ring fusion and C-7 ring structure on fluoroquinolone lethality. Antimicrob. Agents Chemother. 54:5214-5221.
31. Malik, M., X. Zhao, and K. Drlica. 2006. Lethal fragmentation of bacterial chromosomes mediated by DNA gyrase and quinolones. Mol. Microbiol. 61:810-825.
32. Okada, Y., et al. 2000. Assignment of functional amino acids around the active site of human DNA topoisomerase II alpha. J. Biol. Chem. 275:24630-24638.
33. Oppegard, L., et al. 2010. Comparison of in vitro activities of fluoroquinolone- like 2,4- and 1,3-diones. Antimicrob. Agents Chemother. 54:3011-3014.
34. Pan, X., K. Gould, and L. Fisher. 2009. Probing the differential interactions of quinazolinedione PD 0305970 and quinolones with gyrase and topoisomerase IV. Antimicrob. Agents Chemother. 53:3822-3831.
35. Rosen, J. D., N. German, and R. J. Kerns. 2009. Efficient synthesis of the 2-amino-6-chloro-4-cyclopropyl-7-fluoro-5-methoxy-pyrido[1,2-c]pyrimidine- 1,3-dione core ring system. Tetrahedron Lett. 50:785-789.
36. Rustomjee, R., et al. 2008. A phase II study of the sterilising activities of ofloxacin, gatifloxacin and moxifloxacin in pulmonary tuberculosis. Int. J. Tuberc. Lung Dis. 12:128-138.
37. Schmidt, B., A. Burgin, J. Deweese, N. Osheroff, and J. Berger. 2010. A novel and unified two-metal mechanism for DNA cleavage by type II and IA topoisomerases. Nature 465:641-644.
38. Sieradzki, K., R. Roberts, S. Haber, and A. Tomasz. 1999. The development of vancomycin resistance in a patient with methicillin-resistant Staphylococcus aureus infection. N. Engl. J. Med. 340:517-523.
39. Sindelar, G., et al. 2000. Mutant prevention concentration as a measure of fluoroquinolone potency against mycobacteria. Antimicrob. Agents Chemother. 44:3337-3343.
40. Tran, T., et al. 2007. Structure-activity relationships of 3-aminoquinazolinediones, a new class of bacterial type-2 topoisomerase (DNA gyrase and topo IV) inhibitors. Bioorg. Med. Chem. Lett. 17:1312-1320.
41. Tran, T., et al. 2005. Facile synthesis of substituted 3-amino-1H-quinazoline- 2,4-diones. J. Heterocyclic Chem. 42:669-674. (Pubitemid 40741156)
42. Tretter, E., A. Schoeffler, S. Weisfield, and J. Berger. 2010. Crystal structure of the DNA gyrase GyrA N-terminal domain from Mycobacterium tuberculosis. Proteins 78:492-495.
43. Wohlkonig, A., et al. 2010. Structural basis of quinolone inhibition of type IIA topoisomerases and target-mediated resistance. Nat. Struct. Mol. Biol. 17:1152-1153.
44. Zhao, X., and K. Drlica. 2002. Restricting the selection of antibiotic-resistant mutants: measurement and potential uses of the mutant selection window. J. Infect. Dis. 185:561-565.
45. Zhao, X., et al. 1998. Killing of Staphylococcus aureus by C-8-methoxy fluoroquinolones. Antimicrob. Agents Chemother. 42:956-958.
46. Zhao, X., C. Xu, J. Domagala, and K. Drlica. 1997. DNA topoisomerase targets of the fluoroquinolones: a strategy for avoiding bacterial resistance. Proc. Natl. Acad. Sci. U. S. A. 94:13991-13996.
47. Zhou, J., et al. 2000. Selection of antibiotic resistant bacterial mutants: allelic diversity among fluoroquinolone-resistant mutations. J. Infect. Dis. 182:517-525.