Identification of potent inhibitors for salmonella typhimurium quorum sensing via virtual screening and pharmacophore modeling

Combinatorial Chemistry and High Throughput Screening

Volumn 16, Issue 10, 2013, Pages 826-839

  Gnanendra, Shanmugam ^a,c   Mohamed, Syed ^b   Natarajan, Jeyakumar ^c  

^a Selvam Arts and Science College   (India)

^b Sadakathullah Appa College (Autonomous)   (India)

^c BHARATHIAR UNIVERSITY   (India)

Author keywords

Docking; Pharmacophore; Quorum sensing; Salmonella typhimurium; Virtual screening

Indexed keywords

ANTIBIOTIC AGENT; BTB 02340; BTB 02602; BTB 14180; CD 01374; CD 07607; ESSENTIAL AMINO ACID; GK 00709; HTS 01162; KM 10117; N ACYLHOMOSERINE LACTONE; RG 00117; RJF 00047; TRANSCRIPTION FACTOR; TRANSCRIPTION FACTOR SDIA; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL VIRULENCE; DRUG DESIGN; DRUG POTENCY; HALOGENATION; HIGH THROUGHPUT SCREENING; HYDROGEN BOND; IC 50; MOLECULAR DOCKING; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; QUORUM SENSING; SALMONELLA TYPHIMURIUM;

ANTI-BACTERIAL AGENTS; DATABASES, CHEMICAL; MOLECULAR DOCKING SIMULATION; QUORUM SENSING; SALMONELLA TYPHIMURIUM;

EID: 84893713719     PISSN: 13862073     EISSN: 18755402     Source Type: Journal    
DOI: 10.2174/1386207311301010003     Document Type: Article

References (35)

1. Scherer, C.A.; Miller, S.I. Molecular pathogenesis of salmonellae. In: Groisman EA (ed.) Principles of bacterial pathogenesis. Academic, New York, 2001, pp. 266-33.
2. Grein, T.; O'Flanagan, D.; McCarthy, T.; Bauer, D. An outbreak of multidrug-resistant Salmonella typhimurium food poisoning at a wedding reception. Ir. Med. J., 1999, 92, 238-241.
3. Cloeckaert, A.; Chaslus-Dancla, E. Mechanisms of quinolone resistance in Salmonella. Vet. Res., 2001, 32, 291-300.
4. Piddock, L.J. Fluoroquinolone resistance in Salmonella serovars isolated from humans and food animals. FEMS Microbiol. Rev., 2002, 26, 3-16.
5. Russell, A. D. Introduction of biocides into clinical practice and the impact on antibiotic-resistant bacteria. J. Appl. Microbiol. (Suppl.), 2002, 92, 121s-135s.
6. Olson, M. E.; Ceri, H.; Morck, D.W.; Buret, A.G.; Read, R.R. Biofilm bacteria: formation and comparative susceptibility to antibiotics. Can. J. Vet. Res., 2002, 66, 86-92.
7. Fuqua, C.; Parsek, M.R.; Greenberg, E.P. Regulation of gene expression by cell-to-cell communication: acyl-homoserine lactone quorum sensing. Annu. Rev. Genet., 2001, 5, 439-468.
8. Waters, C. M.; Bassler, B.L. Quorum sensing: cell-to-cell communication in bacteria. Annu. Rev. Cell Dev. Biol., 2005, 21, 319-346.
9. Eberhard, A.; Burlingame, A.L.; Eberhard, C.; Kenyon, G.L.; Nealson, H.K.; Oppenheimer, N.J. Structural identification of autoinducer of Photobacterium fischeri luciferase. Biochemistry, 1981, 20, 2444-2449.
10. Marketon, M.M.; Gronquist, M.R.; Eberhard, A.; Gonzalez, J.E. Characterization of the Sinorhizobium meliloti sinR/sinI locus and the production of novel N-acyl homoserine lactones. J. Bacteriol., 2002, 184, 5686-5695.
11. Parsek, M. R.; Greenberg, E.P. Sociomicrobiology: the connections between quorum sensing and biofilms. Trends Microbiol., 2005, 13, 27-33.
12. Michael, B.; Smith, J.N.; Swift, S.; Heffron, F.; Ahmer, B.M. SdiA of Salmonella enterica is a LuxR homolog that detects mixed microbial communities. J. Bacteriol., 2001, 183, 5733-5742.
13. Smith, D.; Wang, J.H.; Swatton, J.E.; Davenport, P.; Price, B.; Mikkelsen, H.; Stickland, H.; Nishikawa, K.; Gardiol, N.; Spring, D.R.; Welch, M. Variations on a theme: diverse N-acyl homoserine lactone-mediated quorum sensing mechanisms in gram-negative bacteria. Sci. Prog., 2006, 89, 167-211.
14. Smith, J.N.; Ahmer, B.M. Detection of other microbial species by Salmonella: expression of the SdiA regulon. J. Bacteriol., 2003, 185, 1357-1366.
15. Defoirdt, T.; Miyamoto, C.M.; Wood, T.K.; Meighen, E.A.; Sorgeloos, P.; Verstraete, W.; Bossier, P. The natural furanone (5Z)-4-bromo-5- (bromomethylene)-3-butyl-2(5H)-furanone disrupts quorum sensing-regulated gene expression in Vibrio harveyi by decreasing the DNA-binding activity of the transcriptional regulator protein luxR. Environ. Microbiol., 2007, 9, 2486-2495.
16. Givskov, M.; de Nys, R.; Manefield, M.; Gram, L.; Maximilien, R.; Eberl, L.; Molin, S.; Steinberg, P.D.; Kjelleberg, S. Eukaryotic interference with homoserine lactone-mediated prokaryotic signalling. J. Bacteriol., 1996, 178, 6618-6622.
17. Joost c.A.Janssens.; Hans steenackers.; Stijn Robijns.; EdithGellens.; Jeremy Levin.; Hui Zhao.; Kim Hermans.; David De coster.; Tine L.Verhoeven.; Kathleen marchal.; Jos Vanderleyden.; dirk E. De Vos; Sigrid c.J.De Keersmaecker. Brominated Furanones inhibit Biofilm Formation by Salmonella enterica Serovar Typhimurium. Appl. Environ. Microbiol., 2008, 74, 6639-6648.
18. Throup, J.P.; Camara, M.; Briggs, G.; Winson, M.K.; Bycroft, B.W.; Williams, P.; Stewart, G.S.A.B. Characterisation of the yenI/yenR locus from Yersinia enterocolitica mediating the synthesis of two quorum sensing signal molecules. Mol. Microbiol., 1995, 17, 345-356.
19. Gnanendra, S.; Anusuya, S.; Natarajan, J. Molecular modeling and active site analysis of SdiA homolog, a putative quorum sensor for Salmonella typhimurium pathogenecity reveals specific binding patterns of AHL transcriptional regulators. J. Mol. Model., 2012, 18, 4709-4719.
20. ACD/ChemSketch Freeware, version 11, Advanced Chemistry Development, Inc., Toronto, ON, Canada, 2006, www.acdlabs.com .
21. Discovery Studio Modeling Environment, Release 2.5, Accelrys Software Inc., San Diego, 2011.
22. Weininger, D. SMILES, a chemical language and information system. Introduction to methodology and encoding rules. J. Chem. Inf. Comput. Sci., 1988, 28, 31-36.
23. Wolf, L.K. Digital briefs: New software and websites for the chemical enterprise. C&EN, 2009, 87, 32.
24. Hans P. Steenackers; Jeremy Levin.; Joost C. Janssens.; Ami De Weerdt.; Jan Balzarini C.; Jos Vanderleyden.; Dirk E. De Vos.; Sigrid C. De Keersmaecker. Structure-activity relationship of brominated 3-alkyl-5-methylene-2(5H)- furanones and alkylmaleic anhydrides as inhibitors of Salmonella biofilm formation and quorum sensing regulated bioluminescence in Vibrio harveyi. Bioorg. Med. Chem., 2010, 18, 5224-5233.
25. Sprague, P.W. Automated chemical hypothesis generation and database searching with catalyst. Perspect. Drug Discov. Des., 1995,3,1-20.
26. Sanam, R.; Vadivelan, S.; Tajne, S.; Narasu, L.; Rambabu, G.; Jagarlapudi, S.A. Discovery of potential ZAP-70 kinase inhibitors: Pharmacophore design, database screening and docking studies. Eur. J. Med. Chem., 2009, 44, 4793-4800
27. Maybridge Database www.maybridge.com/
28. Lipinski, C.A.; Lombardo, F.; Dominy, B.W.; Feeney, P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Del. Rev., 2001, 46, 3-26.
29. Walters, W.P.; Murcko, M.A. Prediction of 'drug-likeness'. Adv. Drug. Deliv. Rev, 2002, 54, 255-271.
30. Rarey, M.; Kramer, B.; Lengauer, T.; Klebe, G. A fast flexible docking method using an incremental construction algorithm. J. Mol. Biol., 1996, 261, 470-89.
31. Stierand, K.; Maab, P.; Rarey, M. Molecular Complexes at a Glance: Automated Generation of two-dimensional Complex Diagrams. Bioinformatics, 2006, 22, 1710-1716.
32. Dyszel, J.L.; Smith, J.N.; Lucas, D.E.; Soares, J.A.; Swearingen, M.C.; Vross, M.A.; Young, G.M.; Ahmer, B.M. Salmonella enteric serovar Typhimurium can detect acyl homoserine lactone production by Yersinia enterocolitica in mice. J. Bacteriol., 2010, 192, 29-37.
33. Smith, J.N.; Dyszel, J.L.; Soares, J.A.; Ellermeier, C.D.; Altier, C.; Lawhon, S.D.; Adams, L.G.; Konjufca, V.; Curtiss III R.; Slauch, J.M.; Ahmer, B.M. SdiA, an N-acylhomoserine lactone receptor, becomes active during the transit of Salmonella enteric through the gastrointestinal tract of turtles. PloS ONE, 2008, 3, e2826.
34. Jiménez-Gómez, P.; Pozuelo de Felipe, M.J.; Llinares Pinell F.; García de los Ríos, J.E. Quorum-sensing in Pseudomonas aeruginosa and Salmonella: Active natural compounds as antagonists. Communicating Current Research and Educational Topics and Trends in Applied Microbiology, 2007, 1, 41-51.
35. de Nys, R.; Wright, A.D.; König, G.M.; Sticher, O. New halogenated furanones from the marine alga Delisea pulchra (cf. fimbriata). Tetrahedron, 1993, 49, 11213-11220.