Discovery of bacterial NAD +-dependent DNA ligase inhibitors: Optimization of antibacterial activity

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 15, 2011, Pages 4556-4560

  Stokes, Suzanne S ^a   Huynh, Hoan ^a   Gowravaram, Madhusudhan ^a   Albert, Robert ^a   Cavero Tomas, Marta ^a   Chen, Brendan ^a   Harang, Jenna ^a   Loch III, James T ^a   Lu, Min ^a   Mullen, George B ^a   Zhao, Shannon ^a   Liu, Ce Feng ^a   Mills, Scott D ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Adenosines; Antibacterial; Bacterial DNA ligase; LigA

Indexed keywords

BACTERIAL DNA LIGASE INHIBITOR; LIGASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG POTENCY; ESCHERICHIA COLI; HAEMOPHILUS INFLUENZAE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE; STRUCTURE ACTIVITY RELATION;

ADENOSINE; ANTI-BACTERIAL AGENTS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; DNA LIGASES; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; MICROBIAL SENSITIVITY TESTS; NAD; PROTEIN STRUCTURE, TERTIARY; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE;

BACTERIA (MICROORGANISMS); LIGA; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE;

EID: 79960374372     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.05.128     Document Type: Article

References (25)

1. D.N. Gilbert, R.J. Guidos, H.W. Boucher, G.H. Talbot, B. Spellberg, J.E. Edwards, W.M. Scheld, J.S. Bradley, and J.G. Bartlett Clin. Infect. Dis. 50 2010 1081
2. S.J. Projan, and P.A. Bradford Curr. Opin. Microbiol. 10 2007 441
3. B. Spellberg, R. Guidos, D. Gilbert, J. Bradley, H. Boucher, W.M. Scheld, J.G. Bartlett, and J. Edwards Jr. Clin. Infect. Dis. 46 2008 155
4. G.H. Talbot, J. Bradley, J.E. Edwards Jr., D. Gilbert, M. Scheld, and J.G. Bartlett Clin. Infect. Dis. 42 2006 657
5. D.J. Payne, M.N. Gwynn, D.J. Holmes, and D.L. Pompliano Nat. Rev. Drug Disc. 6 2007 29
6. I.R. Lehman Science 186 1974 790
7. S. Shuman J. Biol. Chem. 284 2009 17365
8. A.E. Tomkinson, S. Vijayakumar, J.M. Pascal, and T. Ellenberger Chem. Rev. 106 2006 687
9. N. Dwivedi, D. Dube, J. Pandey, B. Singh, V. Kukshal, R. Ramachandran, and R.P. Tripathi Med. Res. Rev. 28 2008 545
10. R.V. Swift, and R.E. Amaro Expert Opin. Drug Discov. 4 2009 1281
11. T.I. Meier, D. Yan, R.B. Peery, K.A. McAllister, C. Zook, S.-B. Peng, and G. Zhao FEBS J. 2008 1
12. H. Brötz-Oesterhelt, I. Knezevic, S. Bartel, T. Lampe, U. Warnecke-Eberz, K. Ziegelbauer, D. Habich, and H. Libischiniski J. Biol Chem. 278 2003 39435
13. G. Ciarrocchi, D.G. MacPhee, L.W. Deady, and L. Tilley Antimicrob. Agents and Chemother. 43 1999 2766
14. Eakin, A.E.; Shapiro, A.; Walkup, G.; Karantzeni, I.; Gao, N.; Yang, W.; Patten, A.; Lahiri, S.; Mills S.D. Presented at the 49th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco, CA, September 2009, abstract F1-1981
15. S.D. Mills, A.E. Eakin, E.T. Buurman, J.V. Newman, N. Gao, H. Huyhn, K.D. Johnson, I. Karantzeni, S. Lahiri, A. Shapiro, G.K. Walkup, W. Yang, and S.S. Stokes Antimirob. Agents and Chemother. 55 2011 1088
16. pH7.4 was determined by a miniaturized shake-flask octanol:water assay using HPLC-UV quantitation. Protein binding was determined by equilibrium dialysis followed by LC-MS/MS quantitation.
17. Stokes, S. S.; Huynh, H.; Gowravaram, M.; Lu, M.; Mullen, G.; Mills, S.D. Presented at the 49th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco, CA, September 2009, abstract F1-1980.
18. -6) Absorption potential 4 0.28 Low 5 3.32 High 6 7.26 High
19. M.R. Singleton, K. Hkansson, D.F. Timson, and D.B. Wigley Structure 7 1999 35
20. K.S. Gajiwala, and C. Pinko Structure 12 2004 1449
21. S.K. Srivastava, B.P. Tripathi, and R. Ramachandran J. Biol. Chem. 280 2005 30273
22. S. Han, J.S. Chang, and M. Griffor Acta Cryst. F65 2009 1078
23. Sequence alignment and similarity determined using ClustalW2. It is made freely available by the European Bioinformatics Institute (EBI) [ http://www.ebi.ac.uk/Tools/msa/clustalw2/ ].
24. Buurman, E.T.; Johnson, K.D.; Laganas, V.; MacCormack, K.; Yang, W.; Mills, S.D. Presented at the 49th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco, CA September, 2009, abstract F1-1982.
25. 1H NMR data, see Cavero-Tomas, M.; Gowravaram, M.; Huynh, H., Ni, H.; Stokes, S. Patent WO 2006040558.