Zinc complexes with 1,2,4-triazole functionalized amino acid derivatives: Synthesis, structure and β-lactamase assay

Inorganica Chimica Acta

Volumn 368, Issue 1, 2011, Pages 21-28

  Naik, Anil D ^a   Beck, Joséphine ^a   Dîrtu, Marinela M ^a   Bebrone, Carine ^b   Tinant, Bernard ^a   Robeyns, Koen ^a   Marchand Brynaert, Jacqueline ^a   Garcia, Yann ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

1,2,4 Triazole; Amino acids; Trinuclear complex; Zinc complexes; Lactamase

Indexed keywords

AMINO ACIDS; BACILLUS CEREUS; BACTERIOLOGY; COMPLEX NETWORKS; CRYSTAL STRUCTURE; ENZYME INHIBITION; HYDROGEN BONDS; IONS; LIGANDS; MOLECULES; SYNTHESIS (CHEMICAL);

1 ,2 ,4-TRIAZOLE; AMINO ACID DERIVATIVES; GLYCINE ETHYL ESTERS; LACTAMASES; OCTAHEDRALLY COORDINATED; SUPRAMOLECULAR NETWORKS; TRINUCLEAR COMPLEX; ZINC COMPLEX;

ZINC COMPOUNDS;

EID: 79952005460     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2010.12.017     Document Type: Article

References (56)

1. E. Boldyreva, Crystalline Amino Acids, a Link between Chemistry, Materials Science and Biology, Springer, Netherlands, 2008. p. 167.
2. S. Pizzarello, A.L. Weber, Science 303 (2004) 1151.
3. S.J. Zuend, M.P. Coughlin, M.P. Lalonde, E.N. Jacobsen, Nature 461 (2009) 968.
4. J.N. Rebilly, J. Bacsa, M.J. Rosseinsky, Chem. Asian J. 4 (2009) 892.
5. L.F. Ma, X.K. Huo, L.Y. Wang, J.G. Wang, Y.T. Fan, J. Solid State Chem. 180 (2007) 1648.
6. M.J. Ingleson, J. Bacsa, M.J. Rosseinsky, Chem. Comm. (2007) 3036.
7. (a) J-J. Zhang, T-L. Sheng, S-M. Hu, S-Q. Xia, G. Leibeling, F. Meyer, Z-Y. Fu, L. Chen, R-B. Fu, X-T. Wu, Chem. Eur. J. 10 (2004) 3963;
8. (b) J.D. Ranford, J.J. Vittal, D. Wu, X. Yang, Angew. Chem., Int. Ed. 23 (1999) 3498;
9. (c) E.V. Anokhina, A.J. Jacobson, J. Am. Chem. Soc. 126 (2004) 3044;
10. (d) A.D. Cutland-Van Noord, J.W. Kampf, V.L. Pecoraro, Angew. Chem., Int. Ed. 41 (2002) 4668;
11. (e) Md.A. Alam, M. Netaji, M. Ray, Angew. Chem., Int. Ed. 42 (2003) 1940;
12. (f) A.K. Patra, S. Dhar, M. Netaji, A.R. Chakravarty, Chem. Commun. (2003) 1562;
13. (g) A. Tovar-Tovar, L. R-Ramirez, A. Campero, A. Romerosa, R. M-Esparza, M.J. Rosales-Hoz, J. Inorg. Biochem. 98 (2004) 1045;
14. (h) S-J. Chiou, J. Innocent, C.G. Riordan, K-C. Lam, L. Liable-Sands, A.L. Rheingold, Inorg. Chem. 39 (2000) 4347;
15. (i) U. Brand, M. Rombach, J. Seebacher, H. Vahrenkamp, Inorg. Chem. 40 (2001) 6151;
16. (j) P.K. Sasmal, A.K. Patra, M. Netaji, A.R. Chakravarty, Inorg. Chem. 46 (2007) 11112.
17. (a) A. Mantion, L. Massuger, P. Rabu, C. Palivan, L.B. McCusker, A. Taubert, J. Am. Chem. Soc. 130 (2008) 2517;
18. (b) B. Wisser, A.-C. Chamayou, R Miller, W. Scherer, C. Janiak, Cryst. Eng. Commun. 10 (2008) 461;
19. (c) B. Wisser, Y. Lu, C. Janiak, Z. Anorg. Allg. Chem. 633 (2007) 1189;
20. (d) L.F. Ma, L.Y. Wang, J.G. Wang, Y.F. Wang, X. Feng, Z. Anorg. Allg. Chem. 632 (2006) 487.
21. A.D. Naik, J. Marchand-Brynaert, Y. Garcia, Synthesis 1 (2008) 149.
22. M.M. Dîrtu, A.D. Naik, J. Marchand-Brynaert, Y. Garcia, J. Phys.: Conf. Ser. 217 (2010) 012085.
23. A.D. Naik, M.M. Dîrtu, A. Leonard, B. Tinant, J. Marchand-Brynaert, B.-L. Su, Y. Garcia, Cryst. Growth Des. 10 (2010) 1798.
24. A. Badarou, M.I. Page, Biochemistry 45 (2006) 10654.
25. M. Hernandez-Valladares, A. Felici, G. Waber, H.W. Adolph, M. Zepperzauer, G.M. Rossolini, G. Amicosante, J.M. Frere, M. Galleni, Biochemistry 36 (1997) 11534.
26. J.H. Ullah, T.R. Walsh, I.A. Talor, D.C. Emery, C.S. Verma, S. Gamblin, J. Spencer, J. Mol. Biol. 284 (1998) 125.
27. R.K. Bartlett, I.R. Humphrey, J. Chem. Soc. C (1967) 664.
28. B. Fohlisch, R. Braun, K.W. Schultze, Angew. Chem., Int. Ed. 6 (1967) 361.
29. M. Ferrari, G. Jommi, G. Miglierini, R. Pagliarin, M. Sisti, Synth. Commun. 22 (1992) 107.
30. D. Seyferth, R.M. Marmor, P.H. Hilbert, J. Org. Chem. 36 (1971) 1379.
31. G.M. Sheldrick, SHELXS-97 and SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
32. Y. Garcia, O. Kahn, L. Rabardel, B. Chansou, J.-P. Tuchagues, Inorg. Chem. 38 (1999) 4663.
33. Y. Boland, P. Herstens, J. Marchand-Brynaert, Y. Garcia, Synthesis 9 (2006) 1504.
34. T.M. Potewar, S.A. Siddiqui, R.J. Lahoti, K.V. Srinivasan, Tetrahedron Lett. 48 (2007) 1721.
35. H.O. Bayer, R.S. Cook, W.C. von Meyer, US Patent 382137628, 1974; Chem. Abstr. 76 (1972) 113224.
36. D. Kantoci, J.K. Denike, W.J. Wechter, Synth. Commun. 26 (1996) 2037.
37. J. Beck, S. Gharbi, A. Herteg-Fernea, L. Vercheval, C. Bebrone, P. Lassaux, A. Zervosen, J. Marchand-Brynaert, Eur. J. Org. Chem. (2009) 85.
38. J. Beck, E. Sauvage, P. Charlier, J. Marchand-Brynaert, Bioorg. Med. Chem. Lett. 18 (2008) 3764.
39. J. Beck, L. Vercheval, C. Bebrone, A. Herteg-Fernea, P. Lassaux, J. Marchand-Brynaert, Bioorg. Med. Chem. Lett. 19 (2009) 3593.
40. K.A. Siddiqui, M. Bolte, G.K. Mehrotra, Inorg. Chim. Acta 363 (2010) 457.
41. J.G. Haasnoot, Coord. Chem. Rev. 200 (2000) 131.
42. U. Heinza, H.-W. Adolph, Cell. Mol. Life Sci. 61 (2004) 2827.
43. A.L. Spek, G. Vos, Acta Crystallogr., Sect. C39 (1983) 990.
44. (a) M. Alagar, R.V. Krishnakumar, A. Mostad, S. Natarajan, Acta Crystallogr., Sect. E61 (2005) o1165;
45. (b) S. Natarajan, N.R. Devi, S.D.M.B. Dhas, S. Athimoolam, Sci. Technol. Adv. Mater. Sci. 9 (2008) 025012.
46. C. Rothenburger, M. Galanski, V.B. Arion, H. Gorls, W. Weigand, B.K. Keppler, Eur. J. Inorg. Chem. (2006) 3746.
47. T.T. Luo, L.-Y. Hsu, C.-C. Su, C.-H. Ueng, T.-C. Tsai, K.-L. Lu, Inorg. Chem. 46 (2007) 1532.
48. R. Taylor, O. Kennard, W. Versichel, J. Am. Chem. Soc. 106 (1984) 244.
49. (a) A. Tamilselvi, G. Mugesh, J. Biol. Inorg. Chem. 13 (2008) 1039;
50. (b) A. Tamilselvi, M. Nethaji, G. Mugesh, Chem. Eur. J. 12 (2006) 7797.
51. P. Macheboeuf, C. Contreras-Martel, V. Job, O. Dideberg, A. Dessen, FEMS Microbiol. Rev. 30 (2006) 673.
52. A. Bryskier, C. Couturier, J. Lowther, Antimicrob. Agents Chemoter. (2005) 410.
53. J. Beck, L. Maton, J.L. Habib Jiwan, J. Marchand-Brynaert, Amino acids, 2010, doi: 10.1007/s00726-010-0697-x.
54. C. Bebrone, Biochem. Pharm. 74 (2007) 1686.
55. L.I. Llarrull, M.F. Tioni, J. Kowalski, B. Bennett, A.J. Vila, J. Biol. Chem. 282 (2007) 30586.
56. J.A. Wolny, S. Rackiwtz, K. Achterhold, Y. Garcia, K. Muffler, A.D. Naik, V. Schunemann, Phys. Chem. Chem. Phys. 12 (2010) 14782.