Benzimidazole-based compounds kill Mycobacterium tuberculosis

European Journal of Medicinal Chemistry

Volumn 75, Issue , 2014, Pages 336-353

  Gong, Yaling ^a   Somersan Karakaya, Selin ^b   Guo, Xiaoyong ^a   Zheng, Purong ^a   Gold, Ben ^b   Ma, Yao ^a   Little, David ^b   Roberts, Julia ^b   Warrier, Thulasi ^b   Jiang, Xiuju ^b   Pingle, Maneesh ^b   Nathan, Carl F ^b   Liu, Gang ^a,c  

^a INSTITUTE OF MATERIA MEDICA   (China)

^b WEILL CORNELL MEDICAL COLLEGE   (United States)

^c Tsinghua University   (China)

Author keywords

Benzimidazole; Drug; Mycobacterium tuberculosis; Nitrofuran; Tuberculosis

Indexed keywords

BENZIMIDAZOLE; DRUG; MYCOBACTERIUM TUBERCULOSIS; NITROFURAN; TUBERCULOSIS;

ANTITUBERCULAR AGENTS; BENZIMIDAZOLES; CELLS, CULTURED; DRUG DESIGN; HUMANS; MACROPHAGES; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP; TUBERCULOSIS;

EID: 84894228421     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.01.039     Document Type: Article

References (28)

1. Tuberculosis 2011 WHO Geneva http://www.who.int/tb/research/en/
2. S.D. Ahuja, D. Ashkin, M. Avendano, R. Banerjee, and M. Bauer et al. Multidrug resistant pulmonary tuberculosis treatment regimens and patient outcomes: an individual patient data meta-analysis of 9153 patients PLoS Med. 9 8 2012 e1001300
3. H.I.M. Boshoffm, and C.E. Barrym III tuberculosis: metabolism and respiration in the absence of growth Nat. Rev. Microbiol. 3 2005 70 80
4. L.G. Wayne, and C.D. Sohaskey Nonreplicating persistence of Mycobacterium tuberculosis Ann. Rev. Microbiol. 55 2001 139 163 (Pubitemid 32978103)
5. World Health Organization Anti-tuberculosis Drug Resistance in the World: Fourth Global Report 2008 WHO Press Geneva, Switzerland
6. S. Claudia, D. Neeraj, C.H. Ruben, Z. Ming, H.H. Young, S. Patricia, and T.C.A. Stewart simple model for testing drugs against non-replicating Mycobacterium tuberculosis Antimicrob. Agents Chemother. 54 10 2010 4150 4158
7. C.V. Smith, V. Sharma, and J.C.D. Sacchettini TB drug discovery: addressing issues of persistence and resistance Tuberculosis 84 2004 45 55 (Pubitemid 38082932)
8. W.R. Bishai, and R.E. Chaisson Short-course chemoprophylaxis for tuberculosis Clin. Chest Med. 18 1 1997 115 122 (Pubitemid 27152508)
9. B. Gold, M. Pingle, S.J. Brickner, N. Shah, and C.F. Nathan et al. Nonsteroidal anti-inflammatory drug sensitizes Mycobacterium tuberculosis to endogenous and exogenous antimicrobials Proc. Natl. Acad. Sci. 109 40 2012 16004 16011
10. V.C. Emery, and A.F. Hassan-Walker Focus on new drugs in development against human cytomegalovirus Drugs 62 2002 1853 1858
11. H. Vanden Bossche, M. Engelen, and F. Rochette Antifungal agents of use in animal health - chemical, biochemical and pharmacological aspects J. Vet. Pharmacol. Ther. 26 2003 5 29 (Pubitemid 36308200)
12. H. Kagechika Novel synthetic retinoids and separation of the pleiotropic retinoidal activities Curr. Med. Chem. 9 2002 591 608 (Pubitemid 34436436)
13. H. Al-Muhaimeed A parallel-group comparison of astemizole and loratadine for the treatment of perennial allergic rhinitis J. Int. Med. Res. 25 1997 175 181 (Pubitemid 27379684)
14. Z. Kazimierczuk, M. Andrzejewska, J. Kaustova, and V. Klimesova Synthesis and antimycobacterial activity of 2-substituted halogenobenzimidazoles Eur. J. Med. Chem. 40 2005 203 208 (Pubitemid 40203161)
15. S.A. Stanley, S.S. Grant, T. Kawate, N. Iwase, M. Shimizu, C. Wivagg, M. Silvis, E. Kazyanskaya, J. Aquadro, A. Golas, M. Fitzgerald, H.Q. Dai, L.X. Zhang, and D.R. Hung Identification of novel inhibitors of M. tuberculosis growth using whole cell based high-throughput screening Chem. Biol. 7 2012 1377 1384
16. L. Li, G. Liu, Z.G. Wang, Y.Y. Yuan, C.X. Zhang, X.H. Wu, and J. Zhang Multi-step parallel synthesis of substituted 5-aminobenzimidazoles in solution-phase J. Comb. Chem. 6 2004 811 821 (Pubitemid 39329438)
17. R.P. Tangallapally, R. Yendapally, R.E. Lee, A.J.M. Lenaerts, and R.E. Lee Synthesis and evaluation of cyclic secondary amine substituted phenyl and benzyl nitrofuranyl amides as novel antituberculosis agents J. Med. Chem. 48 2005 8261 8269 (Pubitemid 43032535)
18. R.P. Tangallapally, Yendapally, K. Hevener, V.C. Jones, A.J.M. Lenaerts, M.R. McNeil, Y.H. Wang, S. Franzblau, and R.E. Lee Synthesis and evaluation of nitrofuranylamides as novel antituberculosis agents J. Med. Chem. 47 21 2004 5276 5283 (Pubitemid 39314926)
19. L.G. Dover, and G.D. Coxon Current status and research strategies in tuberculosis drug development J. Med. Chem. 54 2011 6157 6165
20. L. Zhou, H. Ishizaki, M. Spitzer, K.L. Taylor, N.D. Temperley, S.L. Johnson, P. Brear, P. Gautier, Z. Zeng, A. Mitchell, V. Narayan, E.M. Mcneil, D.W. Melton, T.K. Smith, M. Tyers, N.J. Westwood, and E.E. Patton ALDH2 mediates 5-nitrofuran activity in multiple species Chem. Biol. 19 2012 883 892
21. G. Vogt, and C.F. Nathan In vitro differentiation of human macrophages with enhanced antimycobacterial activity J. Clin. Invest 121 10 2011 3889 3901
22. L. Zolla, and A.M. Timperio Involvement of active oxygen species in protein and oligonucleotide degradation induced by nitrofurans Biochem. Cell. Biol. 83 2005 166 175 (Pubitemid 41113543)
23. M. Vass, K. Hruska, and M. Franek Nitrofuran antibiotics: a review on the application, prohibition and residual analysis Veterinarni Med. 53 9 2008 469 500
24. P. Quillardet, O. Huisman, R. D'ari, and M. Hofnung SOS chromotest, a direct assay of induction of an SOS function in Escherichia coli K-12 to measure genotoxicity Proc. Natl. Acad. Sci. 79 1982 5971 5975 (Pubitemid 13249960)
25. P. Quillardet, and M. Hofnung The SOS chromotest: a review Mutat. Res. Rev. Genet. Toxicol. 297 1993 235 279 (Pubitemid 23287943)
26. P. Quillardet, C.D. Bellecombe, and M. Hofnung The SOS chromotest, a colorimetric bacterial assay for genotoxins: validation study with 83 compounds Mutat. Res. 147 1985 79 95 (Pubitemid 15036828)
27. S. Kevekordes, V. Mersch-Sundermann, C.M. Burghaus, J. Spieberger, H.H. Schmeiser, V.M. Arlt, and H. Dunkelberg SOS induction of selected naturally occurring substances in Escherichia coli (SOS chromotest) Mutat. Res. Genet. Toxicol. Environ. Mutagen. 445 1999 81 91 (Pubitemid 29474936)
28. J. Neuwoehner, A.-K. Reineke, J. Hollender, and A. Eisentrager Ecotoxicity of quinoline and hydroxylated derivatives and their occurrence in groundwater of a tar-contaminated field site Ecotoxicol. Environ. Saf. 72 2009 819 827