Discovery of novel selective inhibitors of Staphylococcus aureus β-ketoacyl acyl carrier protein synthase III

European Journal of Medicinal Chemistry

Volumn 47, Issue 1, 2012, Pages 261-269

  Lee, Jee Young ^a   Jeong, Ki Woong ^a   Shin, Soyoung ^a   Lee, Ju Un ^a   Kim, Yangmee ^a  

^a Konkuk University   (South Korea)

Author keywords

Antibiotics; Fatty acid synthesis; In silico screening; KAS; MRSA

Indexed keywords

[2,4 DICHLORO BENZOIC ACID(2,3,4 TRIHYDROXYBENZYLIDENE)HYDRAZIDE]; [4 [(3 CHLORO PYRAZIN 2 YL)HYDRAZONOMETHYL]BENZENE 1,3 DIOL]; [4 [(5 TRIFLUOROMETHYL PYRIDIN 2 YL)HYDRAZONOMETHYL]BENZENE 1,3 DIOL]; ACYLTRANSFERASE; ACYLTRANSFERASE INHIBITOR; ANTIINFECTIVE AGENT; BETA KETOACYL ACYL CARRIER PROTEIN SYNTHASE 3; THIOLACTOMYCIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIMICROBIAL ACTIVITY; ARTICLE; BINDING AFFINITY; COMPUTER MODEL; CYTOTOXICITY; DRUG BINDING; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; PHARMACOPHORE; PROTEIN EXPRESSION; STAPHYLOCOCCUS AUREUS;

3-OXOACYL-(ACYL-CARRIER-PROTEIN) SYNTHASE; ANIMALS; ANTI-INFECTIVE AGENTS; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MICE; MODELS, MOLECULAR; NIH 3T3 CELLS; PROTEIN CONFORMATION; SPECTROMETRY, FLUORESCENCE; STAPHYLOCOCCUS AUREUS; SUBSTRATE SPECIFICITY;

EID: 84855819579     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.10.052     Document Type: Article

References (48)

1. S. Stefani, and A. Goglio Methicillin-resistant Staphylococcus aureus: related infections and antibiotic resistance Int. J. Infect. Dis. 4 2010 S19 S22
2. E. Tacconelli, G. De Angelis, M.A. Cataldo, E. Pozzi, and R. Cauda Does antibiotic exposure increase the risk of methicillin-resistant Staphylococcus aureus (MRSA) isolation? A systematic review and meta-analysis J. Antimicrob. Chemother. 61 2008 26 38
3. G.C. Schito The importance of the development of antibiotic resistance in Staphylococcus aureus Clin. Microbiol. Infect. 12 2006 3 8
4. E. Turos, K.D. Revell, P. Ramaraju, D.A. Gergeres, K. Greenhalgh, A. Young, N. Sathyanarayan, S. Dickey, D. Lim, M.M. Alhamadsheh, and K. Reynolds Unsymmetric aryl-alkyl disulfide growth inhibitors of methicillin-resistant Staphylococcus aureus and Bacillus anthracis Bioorg. Med. Chem. 16 2008 6501 6508
5. H. Lu, and P.J. Tonge Inhibitors of FabI an enzyme drug target in the bacterial fatty acid biosynthesis pathway Acc. Chem. Res. 41 2008 11 20
6. R.J. Heath, S.W. White, and C.O. Rock Lipid biosynthesis as a target for antibacterial agents Prog. Lipid Res. 40 2001 467 497
7. J.Z. Lu, P.J. Lee, N.C. Waters, and S.T. Prigge Fatty Acid synthesis as a target for antimalarial drug discovery Comb. Chem. High Throughput Screen. 8 2005 15 26
8. C.Y. Lai, and J.E. Cronan Beta-ketoacyl-acyl carrier protein synthase III (FabH) is essential for bacterial fatty acid synthesis J. Biol. Chem. 19 2003 51494 51503
9. R.J. Heath, and C.O. Rock Inhibition of beta-ketoacyl-acyl carrier protein synthase III (FabH) by acyl-acyl carrier protein in Escherichia coli J. Biol. Chem. 3 1996 10996 11000
10. C.E. Christensen, B.B. Kragelund, P. von Wettstein-Knowles, and A. Henriksen Structure of the human beta-ketoacyl [ACP] synthase from the mitochondrial type II fatty acid synthase Protein Sci. 16 2007 261 272
11. Y.M. Zhang, S.W. White, and C.O. Rock Inhibiting bacterial fatty acid synthesis J. Biol. Chem. 281 2006 17541 17544
12. C. Davies, R.J. Heath, S.W. White, and C.O. Rock The 1.8 crystal structure and active-site architecture of beta-ketoacyl-acyl carrier protein synthase III (FabH) from Escherichia coli Structure 8 2000 185 195
13. K.S. Gajiwala, S. Margosiak, J. Lu, J. Cortez, Y. Su, Z. Nie, and K. Appelt Crystal structures of bacterial FabH suggest a molecular basis for the substrate specificity of the enzyme FEBS Lett. 583 2009 2939 2946
14. X. Qiu, A.E. Choudhry, C.A. Janson, M. Grooms, R.A. Daines, J.T. Lonsdale, and S.S. Khandekar Crystal structure and substrate specificity of the beta-ketoacyl-acyl carrier protein synthase III (FabH) from Staphylococcus aureus Protein Sci. 14 2005 2087 2094
15. R.A. Daines, I. Pendrak, K. Sham, G.S. Van Aller, A.K. Konstantinidis, J.T. Lonsdale, C.A. Janson, X. Qiu, M. Brandt, S.S. Khandekar, C. Silverman, and M.S. Head First X-ray cocrystal structure of a bacterial FabH condensing enzyme and a small molecule inhibitor achieved using rational design and homology modeling J. Med. Chem. 46 2003 5 8
16. A.C. Price, K.H. Choi, R.J. Heath, Z. Li, S.W. White, and C.O. Rock Inhibition of beta-ketoacyl-acyl carrier protein synthases by thiolactomycin and cerulenin. Structure and mechanism J. Biol. Chem. 276 2001 6551 6559
17. P. Kim, Y.M. Zhang, G. Shenoy, Q.A. Nguyen, H.I. Boshoff, U.H. Manjunatha, M.B. Goodwin, J. Lonsdale, A.C. Price, D.J. Miller, K. Duncan, S.W. White, C.O. Rock, C.E. Barry 3rd., and C.S. Dowd Structure-activity relationships at the 5-position of thiolactomycin: an intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli J. Med. Chem. 49 2006 159 171
18. J.M. McFadden, S.M. Medghalchi, J.N. Thupari, M.L. Pinn, A. Vadlamudi, K.I. Miller, F.P. Kuhajda, and C.A. Townsend Application of a flexible synthesis of (5R)-thiolactomycin to develop new inhibitors of type I fatty acid synthase J. Med. Chem. 48 2005 946 961
19. Z. Nie, C. Perretta, J. Lu, Y. Su, S. Margosiak, K.S. Gajiwala, J. Cortez, V. Nikulin, K.M. Yager, K. Appelt, and S. Chu Structure-based design, synthesis, and study of potent inhibitors of beta-ketoacyl-acyl carrier protein synthase III as potential antimicrobial agents J. Med. Chem. 48 2005 1596 1609
20. M.M. Alhamadsheh, N.C. Waters, S. Sachdeva, P. Lee, and K.A. Reynolds Synthesis and biological evaluation of novel sulfonyl-naphthalene-1,4-diols as FabH inhibitors Bioorg. Med. Chem. Lett. 18 2008 6402 6405
21. D. Sinha, A.K. Tiwari, S. Singh, G. Shukla, P. Mishra, H. Chandra, and A.K. Mishra Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde Eur. J. Med. Chem. 43 2008 160 165
22. K. Cheng, Q.Z. Zheng, Y. Qian, L. Shi, J. Zhao, and H.L. Zhu Synthesis, antibacterial activities and molecular docking studies of peptide and Schiff bases as targeted antibiotics Bioorg. Med. Chem. 17 2009 7861 7871
23. L. Shi, R.Q. Fang, Z.W. Zhu, Y. Yang, K. Cheng, W.Q. Zhong, and H.L. Zhu Design and synthesis of potent inhibitors of beta-ketoacyl-acyl carrier protein synthase III (FabH) as potential antibacterial agents Eur. J. Med. Chem. 45 2010 4358 4364
24. A. Ashek, and S.J. Cho A combined approach of docking and 3D QSAR study of beta-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors Bioorg. Med. Chem. 14 2006 1474 1482
25. A. Ashek, A.A. San Juan, and S.J. Cho HQSAR study of beta-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors J. Enzym. Inhib. Med. Chem. 22 2007 7 14
26. S. Singh, L.K. Soni, M.K. Gupta, Y.S. Prabhakar, and S.G. Kaskhedikar QSAR studies on benzoylaminobenzoic acid derivatives as inhibitors of beta-ketoacyl-acyl carrier protein synthase III Eur. J. Med. Chem. 43 2008 1071 1080
27. J.Y. Lee, K.W. Jeong, J.U. Lee, D.I. Kang, and Y. Kim Novel E. coli beta-ketoacyl-acyl carrier protein synthase III inhibitors as targeted antibiotics Bioorg. Med. Chem. 17 2009 1506 1513
28. J.Y. Lee, K.W. Jeong, S. Shin, J.U. Lee, and Y. Kim Antimicrobial natural products as beta-ketoacyl-acyl carrier protein synthase III inhibitors Bioorg. Med. Chem. 17 2009 5408 5413
29. CATALYST Version 4.10 Software 2000 Accelrys Inc San Diego, CA
30. N.W. Murrall, and E.K. Davies Conformational freedom in 3-D databases. 1. Techniques J. Chem. Inf. Comput. Sci. 30 1990 312 316
31. P. Purushottamachar, A. Khandelwal, P. Chopra, N. Maheshwari, L.K. Gediya, T.S. Vasaitis, R.D. Bruno, O.O. Clement, and V.C. Njar First pharmacophore-based identification of androgen receptor down-regulating agents: discovery of potent anti-prostate cancer agents Bioorg. Med. Chem. 15 2007 3413 3421
32. K.W. Jeong, J.Y. Lee, D.I. Kang, J.U. Lee, S.Y. Shin, and Y. Kim Screening of flavonoids as candidate antibiotics against Enterococcus faecalis J. Nat. Prod. 72 2009 719 724
33. J.D. MacLowry, M.J. Jaqua, and S.T. Selepak Detailed methodology and implementation of a semiautomated serial dilution microtechnique for antimicrobial susceptibility testing Appl. Microbiol. 20 1970 46 53
34. S. Dixson, W. Brumfitt, and J.M. Hamilton-Miller In vitro activity of six antibiotics against multiresistant staphylococci and other gram-positive cocci Eur. J. Clin. Microbiol. 4 1985 19 23
35. S.C. Park, M.H. Kim, M.A. Hossain, S.Y. Shin, Y. Kim, L. Stella, J.D. Wade, Y. Park, and K.S. Hahm Amphipathic alpha-helical peptide, HP (2-20), and its analogues derived from Helicobacter pylori: pore formation mechanism in various lipid compositions Biochim. Biophys. Acta 1778 2008 229 241
36. A. Risso, M. Zanetti, and R. Gennaro Cytotoxicity and apoptosis mediated by two peptides of innate immunity Cell. Immunol. 189 1998 107 115
37. H. Suttmann, M. Retz, F. Paulsen, J. Harder, U. Zwergel, J. Kamradt, B. Wullich, G. Unteregger, M. Stöckle, and J. Lehmann Antimicrobial peptides of the Cecropin-family show potent antitumor activity against bladder cancer cells BMC Urol. 8 2008 5
38. X. Qiu, C.A. Janson, W.W. Smith, M. Head, J. Lonsdale, and A.K. Konstantinidis Refined structures of beta-ketoacyl-acyl carrier protein synthase III J. Mol. Biol. 307 2001 341 356
39. V. Aparna, G. Rambabu, S.K. Panigrahi, J.A. Sarma, and G.R. Desiraju Virtual screening of 4-anilinoquinazoline analogues as EGFR kinase inhibitors: importance of hydrogen bonds in the evaluation of poses and scoring functions J. Chem. Inf. Model. 45 2005 725 738
40. C.M. Venkatachalam, X. Jiang, T. Oldfield, and M. Waldman LigandFit: a novel method for the shape-directed rapid docking of ligands to protein active sites J. Mol. Graph. Model. 21 2003 289 307
41. B.F. Jensen, H.H.F. Refsgaardb, R. Broc, and P.B. Brockhoff Classification of membrane permeability of drug candidates: a methodological investigation QSAR Comb. Sci. 24 2005 449 457
42. D.F. Veber, S.R. Johnson, H.Y. Cheng, B.R. Smith, K.W. Ward, and K.D. Kopple Molecular properties that influence the oral bioavailability of drug candidates J. Med. Chem. 45 2002 2615 2623
43. B. Mishra, A. Barik, K.I. Priyadarsini, and H. Mohan Fluorescence spectroscopic studies on binding of a flavonoid antioxidant quercetin to serum albumins J. Chem. Sci. 117 2005 641 647
44. S. Rollas, and G.S. Küükgüzel Biological activities of hydrazone derivatives Molecules 12 2007 1910 1939
45. F.R. Pavan, P.I. da, S. Maia, S.R. Leite, V.M. Deflon, A.A. Batista, D.N. Sato, S.G. Franzblau, and C.Q. Leite Thiosemicarbazones semicarbazones dithiocarbazates and hydrazide/hydrazones: anti-Mycobacterium tuberculosis activity and cytotoxicity Eur. J. Med. Chem. 45 2010 1898 1905
46. P. Sensi, N. Maggi, S. Furesz, and G. Maffii Chemical modifications and biological properties of rifamycins Antimicrob. Agents Chemother. (Bethesda) 6 1966 699 714
47. R.C. Moellering Jr. , and M.N. Swartz Drug therapy: the newer cephalosporins N. Engl. J. Med. 294 1976 24 28
48. G.J. Todaro, and H. Green Quantitative studies of the growth of mouse embryo cells in culture and their development into established lines J. Cell Biol. 17 1963 299 313