3D-QSAR study of synthetic furanones as inhibitors of quorum sensing by using CoMFA and CoMSIA approach

Letters in Drug Design and Discovery

Volumn 6, Issue 8, 2009, Pages 568-574

  Sun, Ping Hua ^a   Yang, Zhao Qi ^a   Li, Mao Kang ^a   Chen, Wei Min ^a   Liu, Qian ^a   Yao, Xin Sheng ^a  

^a JINAN UNIVERSITY   (China)

Author keywords

3D QSAR; CoMFA; CoMSIA; Furanones; Quorum sensing

Indexed keywords

FURANONE DERIVATIVE;

ARTICLE; BIOLOGICAL ACTIVITY; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; DRUG STRUCTURE; MOLECULAR MODEL; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUORUM SENSING; STEREOSPECIFICITY;

EID: 70349194679     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018009789353437     Document Type: Article

References (29)

1. Waters C.M.; Bassler B.L. Quorum sensing: cell-to-cell communication in bacteria. Annu. Rev. Cell Dev. Biol., 2005, 21, 319-346. (Pubitemid 41740638)
2. Hastings J.W.; Greenberg E.P. Quorum sensing: the explanation of a curious phenomenon reveals a common characteristic of bacteria. J. Bacteriol., 1999, 18, 2667-2668.
3. Grant D.G.; Jennifer C.O.; Helen E.B. N-Phenylacetanoyl-Lhomoserine lactones can strongly antagonize or superagonize quorum sensing in Vibrio fischeri. ACS Chem. Biol., 2007, 2, 315-320.
4. Eberhard A.; Widrig C.A.; McBath P. Analogs of the autoinducer of bioluminescence in Vibrio fischeri. Arch. Microbiol., 1986, 146, 35-40. (Pubitemid 17003188)
5. Riedel K.; Hentzer M.; Geisenberger O. N-acylhomoserinelactonemediated communication between Pseudomonas aeruginosa and Burkholderia cepacia in mixed biofilms. Microbiology, 2001, 147, 3249. (Pubitemid 33150331)
6. Grossmann G.; Poncioni M.; Bornand M.; Jolivet B.; Neuburger M.; Séquin U. Bioactive butenolides from Streptomyces antibioticus. Tü99: absolute configurations and synthesis of analogs. Tetrahedron, 2003, 59, 3237-3251. (Pubitemid 36513612)
7. Kline T.; Bowman J.; Iglewski B.H.; de Kievit T.; Kakai Y.; Passador L. Novel synthetic analogs of the Pseudomonas autoinducer. Bioorg. Med. Chem. Lett., 1999, 9, 3447-3452.
8. Martinelli D.; Grossmann G.; Urs Séquin.; Brandl H.; Bachofen R. Effects of natural and chemically synthesized furanones on quorum sensing in Chromobacterium violaceum. BMC Microbiol., 2004, 4, 25-34. (Pubitemid 39319739)
9. Kievit T.R.; Iglewski B.H. Bacterial quorum sensing in pathogenic relationships. Infect. Immun., 2000, 68, 4839-4849. (Pubitemid 30672035)
10. Hentzer M.; Eberl L.; Nielsen J.; Givskov M. Quorum sensing: a novel target for the treatment of biofilm infections. Bio. Drugs, 2003, 17, 241-250. (Pubitemid 36999950)
11. Suga H.; Smith K.M. Molecular mechanisms of bacterial quorum sensing as a new drug target. Curr. Opin. Chem. Biol., 2003, 7, 586-591.
12. Cramer III R.D.; Patterson D.E.; Bunce J.D. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc., 1988, 110, 5959-5967.
13. Yang Z.Q.; Sun P.H. 3D-QSAR study of potent inhibitor of phosphodiesterase- 4 by using CoMFA approach. Int. J. Mol. Sci., 2007, 8, 714-722. (Pubitemid 47205129)
14. Dessalew N.; Bharatam P.V.; Singh S.K. 3D-QSAR CoMFA study on aminothiazole derivatives as cyclin-dependent kinase 2 inhibitors. QSAR Comb. Sci., 2007, 26, 85-91. (Pubitemid 46202940)
15. Yang Z.Q.; Sun P.H.; Chen W.M. 3D-QSAR analysis on pyrrolopyridine analogs as mitogen-activated protein kinase-activated protein kinase 2 (MK-2) inhibitors. Lett. Drug Des. Discov., 2007, 4, 557-561. (Pubitemid 350248373)
16. Totrov M. Atomic Property Fields: Generalized 3D pharmacophoric potential for automated ligand superposition, pharmacophore elucidation and 3D QSAR. Chem. Bio. Drug Des., 2008, 71, 15-27.
17. Klebe G.; Abraham U.; Mietzner T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J. Med. Chem., 1994, 37, 4130-4146. (Pubitemid 24379702)
18. Hou T.J.; Zhu L.L.; Chen L.R.; Xu X.J. Mapping the binding site of a large set of quinazoline type EGF-R inhibitors using molecular field analyses and molecular docking studies. J. Chem. Inf. Comput. Sci., 2003, 43, 273-287.
19. Sybyl 7.0; Tripos Associates Inc.; St Louis, US.
20. Streitwieser A. Molecular Orbital Theory for Organic Chemists, Wiley: New York, 1961.
21. Wang J.; Pullman A. A program for flexible lattice energy minimization (FLATER) and its application to the study of protein-lipid copacking. Inst. Biol. Phys. Chim., 1991, 18, 317-342.
22. Delre G.; Pullman B.; Yonezawa T. Electronic structure of the alpha-amino acids of proteins. 1. charge distributions and proton chemical shifts. Biochim. Biophys. Acta, 1963, 75, 153-182.
23. Halgren T.A. Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J. Comput. Chem., 1996, 17, 490-519.
24. Gasteiger J.; Marsili M. Iterative partial equalization of orbital electronegativity: a rapid access to atomic charges. Tetrahedron, 1980, 36, 3219-3228.
25. Gasteiger J.; Marsili M. A new model for calculating atomic charges in molecules. Tetrahedron Lett., 1978, 34, 3181-3184.
26. Bush B.L.; Nachbar R.B. Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA. J. Comput-Aided Mol. Des., 1993, 7, 587-619.
27. 2. J. Mol. Graph. Model, 2002, 20, 269-276.
28. Hawkins D.M.; Basak S.C.; Mills D. QSAR with few compounds and many features. J. Chem. Inf. Comput. Sci., 2001, 41, 663-670. (Pubitemid 33650264)
29. Xiao A.; Zhang Z.; An L.; Xiang Y. 3D-QSAR and docking studies of 3-arylquinazolinethione derivatives as selective estrogen receptor modulators. J. Mol. Model, 2008, 14(2), 149-159.