Optimization of pyrrolamides as mycobacterial gyrb atpase inhibitors: Structure-activity relationship and in vivo efficacy in a mouse model of tuberculosis

Antimicrobial Agents and Chemotherapy

Volumn 58, Issue 1, 2014, Pages 61-70

  Shahul, Hameed P ^a   Solapure, Suresh ^a   Mukherjee, Kakoli ^a   Nandi, Vrinda ^a   Waterson, David ^a   Shandil, Radha ^a   Balganesh, Meenakshi ^a   Sambandamurthy, Vasan K ^a   Raichurkar, Anand Kumar ^a   Deshpande, Abhijeet ^a   Ghosh, Anirban ^a   Awasthy, Disha ^a   Shanbhag, Gajanan ^a   Sheikh, Gulebahar ^a   McMiken, Helen ^a   Puttur, Jayashree ^a   Reddy, Jitendar ^a   Werngren, Jim ^b   Read, Jon ^a   Kumar, Mahesh ^a   Manjunatha, R ^a   Chinnapattu, Murugan ^a   Madhavapeddi, Prashanti ^a   Manjrekar, Praveena ^a   Basu, Reetobrata ^a   Gaonkar, Sheshagiri ^a   Sharma, Sreevalli ^a   Hoffner, Sven ^a   Humnabadkar, Vaishali ^a   Subbulakshmi, Venkita ^a   Panduga, Vijender ^a   more..

^a ASTRAZENECA   (United Kingdom)

^b SWEDISH INSTITUTE FOR INFECTIOUS DISEASE CONTROL   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATASE INHIBITOR; DNA TOPOISOMERASE (ATP HYDROLYSING) B; GYRB ATPASE INHIBITOR; PYRROLE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIBIOTIC RESISTANCE; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DNA SUPERCOILING; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG POTENCY; DRUG PROTEIN BINDING; ENZYME ACTIVITY; ENZYME PURIFICATION; GENE MAPPING; IC 50; IN VIVO STUDY; MINIMUM INHIBITORY CONCENTRATION; MOUSE; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; POINT MUTATION; PRIORITY JOURNAL; PROTEIN DOMAIN; STRUCTURAL HOMOLOGY; STRUCTURE ACTIVITY RELATION; TUBERCULOSIS;

ANIMALS; ANTITUBERCULAR AGENTS; CELL LINE; HUMANS; MICE; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP; TUBERCULOSIS;

EID: 84891510270     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.01751-13     Document Type: Article

References (25)

1. World Health Organization. 2010. World Health Organization tuberculosis fact sheet no. 104. World Health Organization, Geneva, Switzerland. http://www.who.int/mediacentre/factsheets/fs104/en.
2. World Health Organization. 2010. World Health Organization multidrug and extensively drug-resistant TB (M/XDR-TB): 2010 global report on surveillance andresponse.WorldHealthOrganization,Geneva,Switzerland.http://www.who.int/tb/ publications/2010/978924599191/en/index.html.
3. Glaziou P, Floyd K, Korenromp EL, Sismanidis C, Bierrenbach AL, Williams BG, Atun R, Raviglione M. 2011. Lives saved by tuberculosis control and prospects for achieving the 2015 global target for reducing tuberculosis mortality. Bull. World Health Organ. 89:573-582. http://dx.doi.org/10.2471/BLT. 11.087510.
4. Zignol M, van Gemert W, Falzon D, Sismanidis C, Glaziou P, Floyd K, Raviglione MS. 2012. Feb; Surveillance of anti-tuberculosis drug resistance in the world: an updated analysis, 2007 to 2010. Bull. World Health Organ. 90:111-119D. http://dx.doi.org/10.2471/BLT.11.092585.
5. Grosset JH, Singer TG, Bishai WR. 2012. New drugs for the treatment of tuberculosis: hope and reality. Int. J. Tuberc. Lung Dis. 16:1005-1014. http://dx.doi.org/10.5588/ijtld.12.0277.
6. Koul A, Arnoult E, Lounis N, Guillemont J, Andries K. 2011. The challenge of new drug discovery for tuberculosis. Nature 469:483-490. http://dx.doi.org/10.1038/nature09657.
7. Maxwell A. 1997. DNA gyrase as a drug target. Trends Microbiol. 5:102- 109. http://dx.doi.org/10.1016/S0966-842X(96)10085-8.
8. Cole ST, Brosch R, Parkhill J, Garnier T, Churcher C, Harris D, Gordon SV, Eiglmeier K, Gas S, Barry CE, III, Tekaia F, Badcock K, Basham D, Brown D, Chillingworth T, Connor R, Davies R, Devlin K, Feltwell T, Gentles S, Hamlin N, Holroyd S, Hornsby T, Jagels K, Krogh A, McLean J, Moule S, Murphy L, Oliver K, Osborne J, Quail MA, Rajandream MA, Rogers J, Rutter S, Seeger K, Skelton J, Squares R, Squares S, Sulston JE, Taylor K, Whitehead S, Barrell BG. 1998. Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence. Nature 393:537-544. http://dx.doi.org/10.1038/31159.
9. Champoux JJ. 2001. DNA topoisomerases: structure, function, and mechanism. Annu. Rev. Biochem. 70:369-413. http://dx.doi.org/10.1146/annurev. biochem.70.1.369.
10. Corbett KD, Berger JM. 2004. Structure, molecular mechanisms, and evolutionary relationships in DNA topoisomerases. Annu. Rev. Biophys. Biomol. Struct. 33:95-118. http://dx.doi.org/10.1146/annurev.biophys.33.110502.140357.
11. Gellert M, Mizuuchi K, O'Dea MH, Nash HA. 1976. DNA gyrase: an enzyme that introduces superhelical turns into DNA. Proc. Natl. Acad. Sci. U. S. A. 73:3872-3876. http://dx.doi.org/10.1073/pnas.73.11.3872.
12. Levine C, Hiasa H, Marians KJ. 1998. DNA gyrase and topoisomerase IV: biochemical activities, physiological roles during chromosome replication, and drug sensitivities. Biochim. Biophys. Acta 1400:29-43. http://dx.doi.org/10. 1016/S0167-4781(98)00126-2.
13. Eakin AE, Green O, Hales N, Walkup GK, Bist S, Singh A, Mullen G, Bryant J, Embrey K, Gao N, Breeze A, Timms D, Andrews B, Uria- Nickelsen M, Demeritt J, Loch JT, III, Hull K, Blodgett A, Illingworth RN, Prince B, Boriack-Sjodin PA, Hauck S, MacPherson LJ, Ni H, Sherer B. 2012. Pyrrolamide DNA gyrase inhibitors: fragment-based nuclear magnetic resonance screening to identify antibacterial agents. Antimicrob. Agents Chemother. 56:1240-1246.
14. Jayaram R, Gaonkar S, Kaur P, Suresh BL, Mahesh BN, Jayashree R, Nandi V, Bharat S, Shandil RK, Kantharaj E, Balasubramanian V. 2003. Pharmacokinetics-pharmacodynamics of rifampin in an aerosol infection model of tuberculosis. Antimicrob. Agents Chemother. 47:2118-2124. http://dx.doi.org/10. 1128/AAC.47.7.2118-2124.2003.
15. Madhusudan K, Nagaraja V. 1996. Alignment and phylogenetic analysis of type II topoisomerases. J. Biosci. 21:613-629. http://dx.doi.org/10.1007/ BF02703140.
16. Franzblau SG, Witzig RS, McLaughlin JC, Torres P, Madico G, Hernandez A, Degnan MT, Cook MB, Quenzer VK, Ferguson RM, Gilman RH. 1998. Rapid, low-technology MIC determination with clinical Mycobacteriumtuberculosis isolates by using the microplate Alamar Blue assay. J. Clin. Microbiol. 36:362-366.
17. Sherer BA, Hull K, Green O, Basarab G, Hauck S, Hill P, Loch JT, III, Mullen G, Bist S, Bryant J, Boriack-Sjodin A, Read J, DeGrace N, Uria-Nickelsen M, Illingworth RN, Eakin AE. 2011. Pyrrolamide DNA gyrase inhibitors: optimization of antibacterial activity and efficacy. Bioorg. Med. Chem. Lett. 21:7416-7420. http://dx.doi.org/10.1016/j.bmcl.2011.10.010.
18. Karkare S, Chung TT, Collin F, Mitchenall LA, McKay AR, Greive SJ, Meyer JJ, Lall N, Maxwell A. 2013. The naphthoquinone diospyrin is aninhibitor of DNA gyrase with a novel mechanism of action. J. Biol. Chem.288:5149-5156. http://dx.doi.org/10.1074/jbc.M112.419069.
19. Aubry A, Fisher LM, Jarlier V, Cambau E. 2006. First functional characterization of a singly expressed bacterial type II topoisomerase: the enzyme from Mycobacterium tuberculosis. Biochem. Biophys. Res. Commun. 348:158-165. http://dx.doi.org/10.1016/j.bbrc.2006.07.017.
20. Aubry A, Pan XS, Fisher LM, Jarlier V, Cambau E. 2004. Mycobacterium tuberculosisDNAgyrase: interaction with quinolones and correlation with antimycobacterial drug activity. Antimicrob. Agents Chemother. 48: 1281-1288. http://dx.doi.org/10.1128/AAC.48.4.1281-1288.2004.
21. Onodera Y, Tanaka M, Sato K. 2001. Inhibitory activity of quinolones against DNA gyrase of Mycobacterium tuberculosis. J. Antimicrob. Chemother. 47:447-450. http://dx.doi.org/10.1093/jac/47.4.447.
22. Shirude PS, Madhavapeddi P, Tucker JA, Murugan K, Patil V, Basavarajappa H, Raichurkar AV, Humnabadkar V, Hussein S, Sharma S, Ramya VK, Narayan CB, Balganesh TS, Sambandamurthy VK. 2013. Aminopyrazinamides: novel and specific GyrB inhibitors that kill replicating and nonreplicating Mycobacterium tuberculosis. ACS Chem. Biol. 8:519-523. http://dx.doi.org/10.1021/cb300510w.
23. Roue M, Agrawal A, Volker C, Mossakowska D, Mayer C, Bax BD. 2013. Purification, crystallization and preliminary X-ray crystallographicstudies of the Mycobacterium tuberculosis DNA gyrase ATPase domain. Acta Crystallogr. Sect F Struct. Biol. Cryst Commun. 69:679-682.
24. Chopra S, Matsuyama K, Tran T, Malerich JP, Wan B, Franzblau SG, Lun S, Guo H, Maiga MC, Bishai WR, Madrid PB. 2012. Evaluation of gyrase B as a drug target in Mycobacterium tuberculosis. J. Antimicrob.Chemother. 67:415-421. http://dx.doi.org/10.1093/jac/dkr449.
25. Shandil RK, Jayaram R, Kaur P, Gaonkar S, Suresh BL, Mahesh BN, Jayashree R, Nandi V, Bharath S, Balasubramanian V. 2007. Moxifloxacin, ofloxacin, sparfloxacin, and ciprofloxacin against Mycobacterium tuberculosis: evaluation of in vitro and pharmacodynamic indices that best predict in vivo efficacy. Antimicrob. Agents Chemother. 51:576-582. http://dx.doi.org/10.1128/AAC.00414- 06.