3,4-dimethoxyphenyl bis-benzimidazole, a novel DNA topoisomerase inhibitor that preferentially targets Escherichia coli topoisomerase I

Journal of Antimicrobial Chemotherapy

Volumn 67, Issue 12, 2012, Pages 2882-2891

  Bansal, Sandhya ^a,b   Sinha, Devapriya ^a   Singh, Manish ^a,b   Cheng, Bokun ^c   Tse Dinh, Yuk Ching ^c   Tandon, Vibha ^a  

^a UNIVERSITY OF DELHI   (India)

^b UNIVERSITY OF DELHI   (India)

^c NEW YORK MEDICAL COLLEGE   (United States)

Author keywords

DMA; Hoechst 33342; MBCs; MICs; PAEs

Indexed keywords

2 (3,4 DIMETHOXYPHENYL) 5 [5 (4 METHYLPIPERAZIN 1 YL) 1H BENZIMIDAZOL 2 YL] 1H BENZIMIDAZOLE; ANTIBIOTIC AGENT; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE INHIBITOR; ETHIDIUM BROMIDE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; CATALYSIS; CELL VIABILITY; CONTROLLED STUDY; DNA CLEAVAGE; DNA DETERMINATION; DRUG DETERMINATION; DRUG STRUCTURE; ENZYME INHIBITION; ESCHERICHIA COLI; HUMAN; HUMAN CELL; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN;

BENZIMIDAZOLES; DNA TOPOISOMERASES, TYPE I; ESCHERICHIA COLI; HUMANS; MICROBIAL SENSITIVITY TESTS; MICROBIAL VIABILITY; TOPOISOMERASE I INHIBITORS;

EID: 84869436674     PISSN: 03057453     EISSN: 14602091     Source Type: Journal    
DOI: 10.1093/jac/dks322     Document Type: Article

References (37)

1. Kaper JB, Nataro JP, Mobley HL. Pathogenic Escherichia coli. Nat Rev Microbiol 2004; 2: 123-40.
2. Schaeffer AJ, Rajan N, Cao Q et al. Host pathogenesis in urinary tract infections. Int J Antimicrob Agents 2001; 17: 245-51.
3. Biswas D, Gupta P, Prasad R et al. Choice of antibiotic for empirical therapy of acute cystitis in a setting of high antimicrobial resistance. Indian J Med Sci 2006; 60: 53-8.
4. Alt S, Mitchenall LA, Maxwell A et al. Inhibition of DNA gyrase and DNA topoisomerase IV of Staphylococcus aureus and Escherichia coli by aminocoumarin antibiotics. J Antimicrob Chemother 2011; 66: 2061-9.
5. Tse-Dinh YC. Bacterial topoisomerase I as a target for discovery of antibacterial compounds. Nucleic Acids Res 2009; 37: 731-7.
6. Pommier Y, Leo E, Zhang H et al. DNA topoisomerases and their poisoning by anticancer and antibacterial drugs. Chem Biol 2010; 17: 421-33.
7. Wang JC. Cellular roles of DNA topoisomerases: a molecular perspective. Nat Rev Mol Cell Biol 2002; 3: 430-40.
8. Schoeffler AJ, Berger JM. DNA topoisomerases: harnessing and constraining energy to govern chromosome topology. Q Rev Biophys 2008; 41: 41-101.
9. Boege F, Straub T, Kehr A et al. Selected novel flavones inhibit the DNA binding or the DNA religation step of eukaryotic topoisomerase I. J Biol Chem 1996; 271: 2262-70.
10. Bridewell DJ, Finlay GJ, Baguley BC. Differential actions of aclarubicin and doxorubicin: the role of topoisomerase I. Oncol Res 1997; 9: 535-42.
11. Pommier Y. DNA topoisomerase I inhibitors: chemistry, biology, and interfacial inhibition. Chem Rev 2009; 109: 2894-902.
12. Bansal S, Tawar U, Singh M et al. Old class but new dimethoxy analogue of benzimidazole: a bacterial topoisomerase I inhibitor. Int J Antimicrob Agents 2010; 35: 186-90.
13. Singh M, Tandon V. Synthesis and biological activity of novel inhibitors of topoisomerase I: 2-aryl-substituted 2-bis-1H-benzimidazoles. Eur J Med Chem 2011; 46: 659-69.
14. Tawar U, Jain AK, Dwarakanath BS et al. Influence of phenyl ring disubstitution on bisbenzimidazole and terbenzimidazole cytotoxicity: synthesis and biological evaluation as radioprotectors. J Med Chem 2003; 46: 3785-92.
15. Reimer LG, Stratton CW, Reller LB. Minimum inhibitory and bactericidal concentrations of 44 antimicrobial agents against three standard control strains in broth with and without human serum. Antimicrob Agents Chemother 1981; 19: 1050-5.
16. Zhu CX, Tse-Dinh YC. The acidic triad conserved in type IA DNA topoisomerases is required for binding of Mg(II) and subsequent conformational change. J Biol Chem 2000; 275: 5318-22.
17. Domanico PL, Tse-Dinh YC. Mechanistic studies on E. coli DNA topoisomerase I: divalent ion effects. J Inorg Biochem 1991; 42: 87-96.
18. Annamalai T, Dani N, Cheng B et al. Analysis of DNA relaxation and cleavage activities of recombinant Mycobacterium tuberculosis DNA topoisomerase I from a new expression and purification protocol. BMC Biochem 2009; 10: 18.
19. Boger DL, Fink BE, Brunette SR et al. A simple, high-resolution method for establishing DNA binding affinity and sequence selectivity. J Am Chem Soc 2001; 123: 5878-91.
20. Maxwell A, Howells AJ. Overexpression and purification of bacterial DNA gyrase. Methods Mol Biol 1999; 94: 135-44.
21. Deweese JE, Osheroff N. The DNA cleavage reaction of topoisomerase II: wolf in sheep's clothing. Nucleic Acids Res 2009; 37: 738-48.
22. Tse-Dinh YC. Uncoupling of the DNA breaking and rejoining steps of Escherichia coli type I DNA topoisomerase. Demonstration of an active covalent protein-DNA complex. J Biol Chem 1986; 261: 10931-5.
23. Bhat AG, Leelaram MN, Hegde SM et al. Deciphering the distinct role for the metal coordination motif in the catalytic activity of Mycobacterium smegmatis topoisomerase I. J Mol Biol 2009; 393: 788-802.
24. Hsiang YH, Hertzberg R, Hecht S et al. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J Biol Chem 1985; 260: 14873-8.
25. Nelson EM, Tewey KM, Liu LF. Mechanism of antitumor drug action: poisoning of mammalian DNA topoisomerase II on DNA by 4'-(9-acridinylamino)-methanesulfon-m-anisidide. Proc Natl Acad Sci USA 1984; 81: 1361-5.
26. Pommier Y. Topoisomerase I inhibitors: camptothecins and beyond. Nat Rev Cancer 2006; 6: 789-802.
27. Beerman TA, McHugh MM, Sigmund R et al. Effects of analogs of the DNA minor groove binder Hoechst 33258 on topoisomerase II and I mediated activities. Biochim Biophys Acta 1992; 1131: 53-61.
28. Kim JS, Sun Q, Gatto B et al. Structure-activity relationships of benzimidazoles and related heterocycles as topoisomerase I poisons. Bioorg Med Chem 1996; 4: 621-30.
29. Singh MP, Joseph T, Kumar S et al. Synthesis and sequence-specific DNA binding of a topoisomerase inhibitory analog of Hoechst 33258 designed for altered base and sequence recognition. Chem Res Toxicol 1992; 5: 597-607.
30. Sun Q, Gatto B, Yu C et al. Synthesis and evaluation of terbenzimidazoles as topoisomerase I inhibitors. J Med Chem 1995; 38: 3638-44.
31. Liu IF, Sutherland JH, Cheng B et al. Topoisomerase I function during Escherichia coli response to antibiotics and stress enhances cell killing from stabilization of its cleavage complex. J Antimicrob Chemother 2011; 66: 1518-24.
32. Cheng B, Liu IF, Tse-Dinh YC. Compounds with antibacterial activity that enhance DNA cleavage by bacterial DNA topoisomerase I. J Antimicrob Chemother 2007; 59: 640-5.
33. Tang SC, Shapiro TA. Newly identified antibacterial compounds are topoisomerase poisons in African trypanosomes. Antimicrob Agents Chemother 2010; 54: 620-6.
34. Garcia MT, Blazquez MA, Ferrandiz MJ et al. New alkaloid antibiotics that target the DNA topoisomerase I of Streptococcus pneumoniae. J Biol Chem 2011; 286: 6402-13.
35. McHugh MM, Woynarowski JM, Sigmund RD et al. Effect of minor groove binding drugs on mammalian topoisomerase I activity. Biochem Pharmacol 1989; 38: 2323-8.
36. Chen AY, Yu C, Bodley A et al. A new mammalian DNA topoisomerase I poison Hoechst 33342: cytotoxicity and drug resistance in human cell cultures. Cancer Res 1993; 53: 1332-7.
37. Domagala JM, Hanna LD, Heifetz CL et al. New structure-activity relationships of the quinolone antibacterials using the target enzyme. The development and application of a DNA gyrase assay. J Med Chem 1986; 29: 394-404.