Identification through structure-based methods of a bacterial NAD +-dependent DNA ligase inhibitor that avoids known resistance mutations

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 1, 2014, Pages 360-366

  Murphy Benenato, Kerry ^a   Wang, Hongming ^a   McGuire, Helen M ^a   Davis, Hajnalka E ^a   Gao, Ning ^a   Prince, D Bryan ^a   Jahic, Haris ^a   Stokes, Suzanne S ^a   Boriack Sjodin, P Ann ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Adenosine; Antibacterial; NAD+ dependent ligase; Resistance; Thienopyridine

Indexed keywords

ADENOSINE; LIGASE INHIBITOR; NICOTINAMIDE ADENINE DINUCLEOTIDE DEPENDENT DNA LIGASE INHIBITOR; POLYDEOXYRIBONUCLEOTIDE SYNTHASE; THIENOPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; ANTIBIOTIC AGENT; BACTERIAL ENZYME;

ARTICLE; BINDING SITE; BIOCHEMISTRY; CRYSTAL STRUCTURE; DRUG STRUCTURE; HYDROGEN BOND; STREPTOCOCCUS PNEUMONIAE; ANTIBACTERIAL ACTIVITY; BACTERIAL MUTATION; CONTROLLED STUDY; DRUG IDENTIFICATION; ENTEROCOCCUS FAECALIS; HAEMOPHILUS INFLUENZAE; HYDROLYSIS; NONHUMAN; RESISTANCE MUTATION; STAPHYLOCOCCUS AUREUS;

BACTERIA (MICROORGANISMS); LIGA; POSIBACTERIA; STREPTOCOCCUS PNEUMONIAE;

ADENOSINE; ANTIBACTERIAL; NAD(+)-DEPENDENT LIGASE; RESISTANCE; THIENOPYRIDINE;

DNA LIGASES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STREPTOCOCCUS PNEUMONIAE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84891558414     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.11.007     Document Type: Article

References (34)

1. D.J. Payne, M.N. Gwynn, D.J. Holmes, and D.L. Pompliano Nat. Rev. Drug Disc. 6 2007 29
2. L.L. Silver Clin. Microbiol. Rev. 24 2011 71
3. M.N. Alekshun, and S.B. Levy Cell 128 2007 1037
4. I.R. Lehman Science 186 1974 790
5. H. Brötz-Oesterhelt, I. Knezevic, S. Bartel, T. Lampe, U. Warnecke-Eberz, K. Ziegelbauer, D. Häbich, and H. Labischinski J. Biol. Chem. 278 2003 39435
6. T.I. Meier, D. Yan, R.B. Peery, K.A. McAllister, C. Zook, S.-P. Peng, and G. Zhao FEBS J. 275 2008 5258
7. G. Ciarrocchi, D.G. MacPhee, L.W. Deady, and L. Tilley Antimicrob. Agents Chemother. 43 1999 2766
8. S.D. Mills, A.E. Eakin, E.T. Buurman, J.V. Newman, N. Gao, H. Huynh, K.D. Johnson, S. Lahiri, A.B. Shapiro, G.K. Walkup, W. Yang, and S.S. Stokes Antimicrob. Agents Chemother. 55 2011 1088
9. S.S. Stokes, H. Huynh, M. Gowravaram, R. Albert, M. Cavero-Tomas, B. Chen, J. Harang, J.T. Loch, M. Lu, G.B. Mullen, S. Zhao, and C.-F. Liu Bioorg. Med. Chem. Lett. 21 2011 4556
10. R.P. Tripathi, J. Pandey, V. Kukshal, A. Ajay, M. Mishra, D. Dube, D. Chopra, R. Dwivedi, V. Chaturvedi, and R. Ramachandran Med. Chem. Commun. 2 2011 371
11. W. Gu, T. Wang, F. Maltais, B. Ledford, J. Kennedy, Y. Wei, C.H. Gross, J. Parsons, L. Duncan, A.S.J. Ryan, C. Moody, E. Perola, and J. Green Bioorg. Med. Chem. Lett. 22 2012 3693
12. T. Wang, L. Duncan, W. Gu, H. O'Dowd, Y. Wei, E. Perola, J. Parsons, C.H. Gross, C.S. Moody, A.S.J. Ryan, and P.S. Charifson Bioorg. Med. Chem. Lett. 22 2012 3699
13. E.T. Buurman, V.A. Laganas, C.F. Liu, and J.I. Manchester ACS Med. Chem. Lett. 3 2012 663
14. J.-P. Surivet, R. Lange, C. Hubschwerlen, W. Keck, J.-L. Specklin, D. Ritz, D. Bur, H. Locher, P. Seiler, D.S. Strasser, L. Prade, C. Kohl, C. Schmitt, G. Chapoux, E. Ilhan, N. Ekambaram, A. Athanasiou, A. Knezevic, D. Sabato, A. Chambovey, M. Gaertner, M. Enderlin, M. Boehme, V. Sippel, and P. Wyss Bioorg. Med. Chem. Lett. 22 2012 6705
15. A.E. Tomkinson, S. Vijayakumar, J.M. Pascal, and T. Ellenberger Chem. Rev. 106 2012 687
16. S. Shuman J. Biol. Chem. 284 2009 17365
17. L. Silver Nat. Rev. Drug Disc. 6 2007 41
18. H. Jahic, C.F. Liu, J. Thresher, S. Livchak, H. Wang, and D. Ehmann Biochem. Pharmacol. 84 2012 654
19. R.L. van Montfort, and P. Workman Trends Biotechnol. 27 2009 315
20. S.K. Grant Cell Mol. Life Sci. 66 2009 1163
21. J. Singh, R.C. Petter, and A.F. Kluge Curr. Opin. Chem. Biol. 14 2010 475
22. J.R. Miller, S. Dunham, I. Mochalkin, C. Banotai, M. Bowman, S. Buist, B. Dunkle, D. Hanna, J. Harwood, M.D. Huband, A. Karnovsky, M. Kuhn, C. Limberakis, J.Y. Liu, S. Mehrens, W.T. Mueller, L. Narasimhan, A. Ogden, J. Ohren, P.J.V.N. Vara, J.A. Shelly, L. Skerlos, M. Sulavik, V.H. Thomas, S. VanderRoest, L. Wang, Z. Wang, A. Whitton, T. Zhu, and C.K. Stover Proc. Natl. Acad. Sci. U.S.A. 106 2009 1737
23. I. Mochalkin, J.R. Miller, L. Narasimhan, V. Thanabal, P. Erdman, P.B. Cox, J.V.N.V. Prasad, S. Lightle, M.D. Huband, and C.K. Stover ACS Chem. Biol. 4 2009 473
24. J.I. Manchester, D.D. Dussault, J.A. Rose, P.A. Boriack-Sjodin, M. Uria-Nickelsen, G. Ioannidis, S. Bist, P. Fleming, and K.G. Hull Bioorg. Med. Chem. Lett. 22 2012 5150
25. J. Yang, E. Ten, F. Lynn, N. Xuong, and S.S. Taylor J. Mol. Biol. 336 2004 473
26. A.K. Ghose, T. Herbertz, D.A. Pippin, J.M. Salvino, and J.P. Mallamo J. Med. Chem. 5 2008 5149
27. G.E. de Kloe, D. Bailey, R. Leurs, and I.J. de Esch Drug Discovery Today 14 2009 630
28. L. Abbott, P. Betschmann, A. Burchat, D.J. Calderwood, H. Davis, P. Hrnciar, G.C. Hirst, B. Li, M. Morytko, K. Mullen, and B. Yang Bioorg. Med. Chem. Lett. 17 2007 1167
29. Talamas F.X., Wang B. WO2005105809A1, 2005.
30. K.S. Gajiwala, and C. Pinko Structure 12 2004 1449
31. D.C. Rees, M. Congreve, C.W. Murray, and R. Carr Nat. Rev. Drug Disc. 3 2004 660
32. S. Schultes, C. de Graaf, E.E.J. Haasksma, I.J.P. de Esch, R. Leurs, and O. Krämer Drug Discovery Today 7 2010 157
33. Luk K., Mcdermott L.A., Rossman P.L., Wovkulich P.M., Zhang Z. US20050256154A1, 2005.
34. M. Orita, K. Ohno, and T. Niimi Drug Discovery Today 14 2009 321