[en] Coordinating abilities of 4R-1,2,4-triazole derivatives (R = glycine ethyl ester (L1), glycine (L2), diethylamino
malonate (L3), methionine (L4) and diethyl aminomethylphosphonate (L5)) towards ZnII ions have
been studied in solution, in solid state and versus three zinc-b-lactamases. The crystal structure of
[Zn3(L4)6(H2O)6] (6) is described; it is the first crystal structure involving a 1,2,4-triazole functionalized
methionine. It forms a trinuclear complex with central zinc octahedrally coordinated by only L4, whereas
terminal zinc ions coordination sphere is completed by three water molecules. L4 exhibits a dual functionality
of a bridging bidentate ligand as well as an anion. A dense hydrogen bonding network connects
these trinuclear entity into a 3D supramolecular network. The ZnII ions in 6 are held at equidistance
(3.848 Å) which coincidently matches with the corresponding Zn Zn distance in the binuclear zinc
enzyme from Bacillus cereus (3.848 and 4.365 Å). Among L1–L5 screened for b-lactamase assay, L4 shows
modest inhibition for BcII enzyme.
Disciplines :
Biochemistry, biophysics & molecular biology
Author, co-author :
Naik, Anil; Université Catholique de Louvain - UCL > Institute of Condensed Matter and Nanosciences
Beck, Joséphine; Université Catholique de Louvain - UCL > Institute of Condensed Matter and Nanosciences
Dîrtu, Marinela; Université Catholique de Louvain - UCL > Institute of Condensed Matter and Nanosciences
Bebrone, Carine ; Université de Liège - ULiège > Centre d'Ingénierie des Protéines
Tinant, Bernard; Université Catholique de Louvain - UCL > Institute of Condensed Matter and Nanosciences
Robeyns, Koen; Université Catholique de Louvain - UCL > Institute of Condensed Matter and Nanosciences
Marchand-Brynaerts, Jacqueline; Université Catholique de Louvain - UCL > Institute of Condensed Matter and Nanosciences
Garcia, Yann; Université Catholique de Louvain - UCL > Institute of Condensed Matter and Nanosciences
Language :
English
Title :
Zinc complexes with 1,2,4-triazole functionalized amino acid derivatives: Synthesis, structure and b-lactamase assay
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] Interuniversity attraction poles IAP-VI (P6/17) INANOMAT and IAP-VI (P6/19) PROFUSA Concerted Research Action of the ‘‘Communauté Française de Belgique’’ allotted by the Académie Universitaire Louvain
(e) Md.A. Alam, M. Netaji, M. Ray, Angew. Chem., Int. Ed. 42 (2003) 1940;
(f) A.K. Patra, S. Dhar, M. Netaji, A.R. Chakravarty, Chem. Commun. (2003) 1562;
(g) A. Tovar-Tovar, L. R-Ramirez, A. Campero, A. Romerosa, R. M-Esparza, M.J. Rosales-Hoz, J. Inorg. Biochem. 98 (2004) 1045;
(h) S-J. Chiou, J. Innocent, C.G. Riordan, K-C. Lam, L. Liable-Sands, A.L. Rheingold, Inorg. Chem. 39 (2000) 4347;
(i) U. Brand, M. Rombach, J. Seebacher, H. Vahrenkamp, Inorg. Chem. 40 (2001) 6151;
(j) P.K. Sasmal, A.K. Patra, M. Netaji, A.R. Chakravarty, Inorg. Chem. 46 (2007) 11112.
(a) A. Mantion, L. Massuger, P. Rabu, C. Palivan, L.B. McCusker, A. Taubert, J. Am. Chem. Soc. 130 (2008) 2517;
(b) B. Wisser, A.-C. Chamayou, R Miller, W. Scherer, C. Janiak, Cryst. Eng. Commun. 10 (2008) 461;
(c) B. Wisser, Y. Lu, C. Janiak, Z. Anorg. Allg. Chem. 633 (2007) 1189;
(d) L.F. Ma, L.Y. Wang, J.G. Wang, Y.F. Wang, X. Feng, Z. Anorg. Allg. Chem. 632 (2006) 487.
A.D. Naik, J. Marchand-Brynaert, Y. Garcia, Synthesis 1 (2008) 149.
M.M. Dîrtu, A.D. Naik, J. Marchand-Brynaert, Y. Garcia, J. Phys.: Conf. Ser. 217 (2010) 012085.
A.D. Naik, M.M. Dîrtu, A. Leonard, B. Tinant, J. Marchand-Brynaert, B.-L. Su, Y. Garcia, Cryst. Growth Des. 10 (2010) 1798.
A. Badarou, M.I. Page, Biochemistry 45 (2006) 10654.
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.
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.
R.K. Bartlett, I.R. Humphrey, J. Chem. Soc. C (1967) 664.
B. Fohlisch, R. Braun, K.W. Schultze, Angew. Chem., Int. Ed. 6 (1967) 361.
M. Ferrari, G. Jommi, G. Miglierini, R. Pagliarin, M. Sisti, Synth. Commun. 22 (1992) 107.
D. Seyferth, R.M. Marmor, P.H. Hilbert, J. Org. Chem. 36 (1971) 1379.
G.M. Sheldrick, SHELXS-97 and SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
Y. Garcia, O. Kahn, L. Rabardel, B. Chansou, J.-P. Tuchagues, Inorg. Chem. 38 (1999) 4663.
Y. Boland, P. Herstens, J. Marchand-Brynaert, Y. Garcia, Synthesis 9 (2006) 1504.