Synthesis and kinetic testing of new inhibitors for a metallo-β- lactamase from Klebsiella pneumonia and Pseudomonas aeruginosa

European Journal of Medicinal Chemistry

Volumn 46, Issue 12, 2011, Pages 6075-6082

  Mohamed, Mosaad S ^a   Hussein, Waleed M ^a,b   McGeary, Ross P ^b   Vella, Peter ^b   Schenk, Gerhard ^b,c   Abd El Hameed, Rania H ^a  

^a Ein Helwan   (Egypt)

^b UNIVERSITY OF QUEENSLAND   (Australia)

^c NATIONAL UNIVERSITY OF IRELAND   (Ireland)

Author keywords

Metallo lactamase inhibitors; Pyrrole; Pyrrolo 2,3 d pyrimidine; Structure activity relationship

Indexed keywords

2 [7 (4 METHOXYPHENYL) 5,6 DIPHENYL 7H PYRROLO[2,3 D]PYRIMIDIN 4 YLIDENE]MALONITRILE; 2 AMINO 1 (4 METHOXYPHENYL) 4 PHENYL 1H PYRROLE 3 CARBONITRILE; 2 AMINO 1 (4 METHYLPHENYL) 4 PHENYL 1H PYRROLE 3 CARBONITRILE; 4 CHLORO 7 (4 METHOXYPHENYL) 5,6 DIPHENYL 7H PYRROLO[2,3 D]PYRIMIDINE; 4 CHLORO 7 (4 METHYLPHENYL) 5 PHENYL 7H PYRROLO[2,3 D]PYRIMIDINE; 4 CHLORO 7 (4 METHYLPHENYL) 5,6 DIPHENYL 7H PYRROLO[2,3 D]PYRIMIDINE; 7 (4 METHOXYPHENYL) 5 PHENYL 7H PYRROLO[2,3 D]PYRIMIDIN 4(3H) ONE; 7 (4 METHYLPHENYL) 8,9 DIPHENYL 7H PYRROLO[3,2 E][1,2,4]TRIAZOLO[4,3 C]PYRIMIDINE 3 THIONE; ANTIBIOTIC AGENT; BETA LACTAMASE INHIBITOR; METALLO BETA LACTAMASE; N BENZYLIDENE N' [7 (4 METHYLPHENYL) 5,6 DIPHENYL 7H PYRROLO[2,3 D]PYRAMIDIN 4 YL]HYDRAZINE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG DETERMINATION; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SPECIFICITY; KLEBSIELLA PNEUMONIAE; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; NONHUMAN; PSEUDOMONAS AERUGINOSA;

BETA-LACTAMASES; ENZYME INHIBITORS; HUMANS; KLEBSIELLA INFECTIONS; KLEBSIELLA PNEUMONIAE; PSEUDOMONAS AERUGINOSA; PSEUDOMONAS INFECTIONS; PYRROLES;

EID: 80955151611     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.10.030     Document Type: Article

References (58)

1. A. Felici, G. Amicosante, A. Oratore, R. Strom, P. Ledent, B. Joris, L. Fanuel, and J.M. Frere Biochem. J. 291 1993 151 155
2. P. Lassaux, M. Hamel, M. Gulea, H. Delbruck, P.S. Mercuri, L. Horsfall, D. Dehareng, M. Kupper, J.M. Frere, K. Hoffmann, M. Galleni, and C. Bebrone J. Med. Chem. 53 2010 4862 4876
3. S. Ohsuka, Y. Arakawa, T. Horii, H. Ito, and M. Ohta Antimicrob. Agents Chemother. 39 1995 1856 1858
4. C. Bebrone Biochem. Pharmacol. 74 2007 1686 1701
5. M.W. Crowder, J. Spencer, and A.J. Vila Acc. Chem. Res. 39 2006 721 728
6. J. Moran-Barrio, J.M. Gonzalez, M.N. Lisa, A.L. Costello, M. Dal Peraro, P. Carloni, B. Bennett, D.L. Tierney, A.S. Limansky, A.M. Viale, and A.J. Vila J. Biol. Chem. 282 2007 18286 18293
7. R. Paul-Soto, R. Bauer, J.M. Frere, M. Galleni, W. Meyer-Klaucke, H. Nolting, G.M. Rossolini, D. de Seny, M. Hernandez-Valladares, M. Zeppezauer, and H.W. Adolph J. Biol. Chem. 274 1999 13242 13249
8. N. Mitic, S.J. Smith, A. Neves, L.W. Guddat, L.R. Gahan, and G. Schenk Chem. Rev. 106 2006 3338 3363
9. J. Li, R.L. Nation, J.D. Turnidge, R.W. Milne, K. Coulthard, C.R. Rayner, and D.L. Paterson Lancet Infectious Dis. 6 2006 589 601
10. D.M. Livermore Clin. Infect. Dis. 34 2002 634 640
11. A.M. Almerico, P. Diana, P. Barraja, G. Dattolo, F. Mingoia, A.G. Loi, F. Scintu, C. Milia, I. Puddu, and P. La Colla Farmaco 53 1998 33 40
12. D. Baucke, U. Lange, H. Mack, T. Pfeiffer, W. Seitz, T. Zierke, H.W. Hoffken, W. Hornberger, (BASF Aktiengesellschaft, Germany). Application: WO, (1998), 37 pp.
13. T. Iihama, K. Hagiwara, S. Maruge, S. Sano, S. Shimoda, Y. Horikoshi, (Nippon Soda Co., Ltd., Japan). Application: JP, (1998), 48 pp.
14. Y. Mizuno, T. Itoh, K.A. Watanabe, S. Suzaki, and M. Ikehara J. Org. Chem. 28 1963 3329 3331
15. B.L. Reed, R.A. Farlow, (American Cyanamid Co., USA; BASF AG). Application: EP (1999), 12 pp.
16. R.L. Tolman, R.K. Robins, and L.B. Townsend J. Am. Chem. Soc. 91 1969 2102 2108
17. M. Biava, R. Fioravanti, G.C. Porretta, D. Deidda, C. Maullu, and R. Pompei Bioorg. Med. Chem. Lett. 9 1999 2983 2988
18. M. Biava, G.C. Porretta, D. Deidda, R. Pompei, A. Tafi, and F. Manetti Bioorg. Med. Chem. 11 2003 515 520
19. Q. Dang, and J.E. Gomez-Galeno J. Org. Chem. 67 2002 8703 8705
20. A. Gangjee, X. Lin, and S.F. Queener J. Med. Chem. 47 2004 3689 3692
21. G.H. Jana, S. Jain, S.K. Arora, and N. Sinha Bioorg. Med. Chem. Lett. 15 2005 3592 3595
22. S. Petruso, S. Bonanno, S. Caronna, M. Ciofalo, B. Maggio, and D. Schillaci J. Heterocycl. Chem. 31 1994 941 945
23. M.V. Raimondi, S. Cascioferro, D. Schillaci, and S. Petruso Eur. J. Med. Chem 41 2006 1439 1445
24. K.V. Rao J. Med. Chem. 11 1968 939 941
25. D. Schillaci, S. Petruso, and V. Sciortino Int. J. Antimicrob. Agents 25 2005 338 340
26. A. Gangjee, H.D. Jain, and R.L. Kisliuk Bioorg. Med. Chem. Lett. 15 2005 2225 2230
27. H. Kasai, Z. Ohashi, F. Harada, S. Nishimura, N.J. Oppenheimer, P.F. Crain, J.G. Liehr, D.L.V. Minden, and J.A. McCloskey Biochemistry 14 1975 4198 4208
28. R.J. Suhadolnik, Wiley-Interscience, New York, NY (1970).
29. E. Declercq, J. Balzarini, D. Madej, F. Hansske, and M.J. Robins J. Med. Chem. 30 1987 481 486
30. R.A. Finch, G.R. Revankar, and P.K. Chan AntiCancer Drug Des. 12 1997 205 215
31. P.K. Gupta, S. Daunert, M.R. Nassiri, L.L. Wotring, J.C. Drach, and L.B. Townsend J. Med. Chem. 32 1989 402 408
32. M.K. Kim, Y.H. Cho, J.M. Kim, M.W. Chun, and C.H. Lee J. Microbiol. Biotechnol. 13 2003 607 612
33. S.H. Krawczyk, M.R. Nassiri, L.S. Kucera, E.R. Kern, R.G. Ptak, L.L. Wotring, J.C. Drach, and L.B. Townsend J. Med. Chem. 38 1995 4106 4114
34. L. Sverak, R.A. Bonar, A.J. Langlois, and J.W. Beard BBA Nucleic Acids Protein Synth. 224 1970 441 450
35. W.L. Wilson Cancer Chemother. Rep. 52 1968 301 303
36. G. Dannhardt, W. Kiefer, G. Kramer, S. Maehrlein, U. Nowe, and B. Fiebich Eur. J. Med. Chem. 35 2000 499 510
37. E. Fernandes, D. Costa, S.A. Toste, J. Lima, and S. Reis Free Radical Bio. Med. 37 2004 1895 1905
38. S.E. de Laszlo, C. Hacker, B. Li, D. Kim, M. MacCoss, N. Mantlo, J.V. Pivnichny, L. Colwell, G.E. Koch, M.A. Cascieri, and W.K. Hagmann Bioorg. Med. Chem. Lett. 9 1999 641 646
39. A. Goel, N. Agarwal, F.V. Singh, A. Sharon, P. Tiwari, M. Dixit, R. Pratap, A.K. Srivastava, P.R. Maulik, and V.J. Ram Bioorg. Med. Chem. Lett. 14 2004 1089 1092
40. S. Fukigai, J. Alba, S. Kimura, T. Iida, N. Nishikura, Y. Ishii, and K. Yamaguchi Int. J. Antimicrob. Agents 29 2007 306 310
41. K.G. Kerr, and A.M. Snelling J. Hosp. Infect. 73 2009 338 344
42. A.P. Penteado, M. Castanheira, A.C.C. Pignatari, T. Guimaraes, E.M. Mamizuka, and A.C. Gales Diagn. Micr. Infec. Dis. 63 2009 87 91
43. P. Vella, W.M. Hussein, E.W.W. Leung, D. Clayton, D.L. Ollis, N. Mitic, G. Schenk, and R.P. McGeary Bioorg. Med. Chem. Lett. 21 2011 3282 3285
44. S. Ktari, G. Arlet, B. Mnif, V. Gautier, F. Mahjoubi, M. Ben Jmeaa, M. Bouaziz, and A. Hammami Antimicrob. Agents Chemother. 50 2006 4198 4201
45. B. Libisch, M. Gacs, K. Csiszar, M. Muzslay, L. Rokusz, and M. Fuzi Antimicrob. Agents Chemother. 48 2004 3576 3578
46. J.H. Toney, G.G. Hammond, P.M.D. Fitzgerald, N. Sharma, J.M. Balkovec, G.P. Rouen, S.H. Olson, M.L. Hammond, M.L. Greenlee, and Y.D. Gao J. Biol. Chem. 276 2001 31913 31918
47. M.S. Mohamed, R.A. El-Domany, and R.H. Abd El-Hameed Acta Pharmacol. 59 2009 145 158
48. M.S. Mohamed, A.E. Rashad, M.E.A. Zaki, and S.S. Fatahala Acta Pharm. (Zagreb, Croatia) 55 2005 237 249
49. C.G. Dave, and R.D. Shah J. Heterocycl. Chem. 35 1998 1295 1300
50. A. Jorgensen, K.A. El-Bayouki, and E.B. Pedersen J. Heterocycl. Chem. 22 1985 859 869
51. A.E. Rashad, M.E.A. Zaki, S.S. Fatahalla, and M.S. Mohamed Arch. Pharmaz. Chem. Life Sci. 339 2006 662 669
52. A. El-Ghanam Phosphorus Sulfur 178 2003 863 868
53. O.A. Fathalla, I.F. Zeid, M.E. Haiba, A.M. Soliman, Sh.I. Abd-Elmoez, and W.S. El-Serwy World J. Chem. 4 2009 127 132
54. M.I. Hossain, and M.M.H. Bhuiyan J. Sci. Res. 1 2009 317 325
55. C. Bebrone, C. Moali, F. Mahy, S. Rival, J.D. Docquier, G.M. Rossolini, J. Fastrez, R.F. Pratt, J.M. Frere, and M. Galleni Antimicrob. Agents Chemother. 45 2001 1868 1871
56. A.W. Schuttelkopf, and D.M.F. van Aalten Acta Crystallogra D 60 2004 1355 1363
57. N. Laraki, N. Franceschini, G.M. Rossolini, P. Santucci, C. Meunier, E. de Pauw, G. Amicosante, J.M. Frere, and M. Galleni Antimicrob. Agents Chemother. 43 1999 902 906
58. I.H. Segel Enzyme Kinetics: Behaviour and Analysis of Rapid Equilibria and Steady-state Equilibria 1993 John Wiley and Sons New York