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International Letters of Chemistry, Physics and Astronomy
Volume 64


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Molecular and Semi-Empirical Mechanic Studies of Copper-Histamine Chloride Complex

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In the present work, we describe and characterized the molecular structure and molecular orbital of Cu (His)Cl2 by two methods: molecular mechanic and semi-empirical PM3 simulations. First, we determine the geometry structural properties of the Cu (Hist)Cl2 complex by molecular mechanic method. Then we compare the calculations method with the experimental data of Cu (His)Cl2 crystal complex. We find that the optimized parameters obtained by MM method are in good agreement with those observed experimentally. After, we evaluate the quantum chemical parameters using PM3 simulations and we discuss the chemical reactivity of Cu (II) ion and the stability of Cu (His)Cl2 molecule. We obtain a large gap with PM3 method. We evaluate the electrophilicity index of the complex. We also calculate the deformation energy. We deduce from quantum calculations that Cu (Hist)Cl2 molecule has high chemical reactivity and is more stable. Finally, we calculate the relative and average errors to estimate the quality of each method. We show that average errors vary as follow: for bonds are 7.833 and 2.692 %, and for angles are 7.755 and 5.309 % using MM+ and PM3 respectively. We conclude that both molecular mechanic and semi-empirical calculations agree very well with the experimental data.


International Letters of Chemistry, Physics and Astronomy (Volume 64)
R. Mahboub and S. Louhibi, "Molecular and Semi-Empirical Mechanic Studies of Copper-Histamine Chloride Complex", International Letters of Chemistry, Physics and Astronomy, Vol. 64, pp. 34-44, 2016
Online since:
Feb 2016

[1] M. Gillard, Ch van der. Perren, N. Moguilevsky, R. Massingham, P. Chatelain, Binding characteristics of cetirizine and levocetirizine to human H(1) histamine receptors: contribution of Lys(191) and Thr(194), Mol. Pharmacol. 61 (2002) 391-399.

[2] H. Fukui, K. Fujimoto, H. Mizuguchi, K. Sakamoto, Y. Horio, S. Takai, K. Yamada, S. Ito, Molecular cloning of the human histamine H1 receptor gene, Biochem. Biophys. Res. Commun. 204 (1994) 894-901.

[3] H. Nonaka, S. Otaki, E. Ohshima, M. Kono, H. Kaser, K. Ohta, H. Fukui, M. Ichimura, Unique binding pocket for KW-4679 in the histamine H1 receptor, Eur. J. Pharmacol. 345 (1998) 111-117.

[4] M. Bruysters, H.H. Pertz, A. Teunissen, R.A. Bakker, M. Gillard, P. Chatelain, W. Schunack, H. Timmerman, R. Leurs, Mutational analysis of the histamine H1-receptor binding pocket of histaprodifens, Eur. J. Pharmacol. 487 (2004) 55-63.

[5] M. Bruysters, A. Jongejan, M. Gillard, F. van der Manakker, R.A. Bakker, P. Chatelain, R. Leurs, Pharmacological differences between human and guinea pig histamine H1 receptors: Asn84 (2. 61) as key residue within an additional binding pocket in the H1 receptor, Mol. Pharmacol. 67 (2005).

[6] A. Torreggiani, M. Tamba, S. Bonora, G. Fini, Biopolymers. Raman and IR study on copper binding of histamine, 72 (2003) 290-298.

[7] E.W. Wilson, M.H. Kasparian, R.B. Martin, Binding of copper (II) to potentially tridentate amino acid ligands, J. Am. Chem. Soc. 92 (1970) 5365-5372.

[8] K. Wieland, A.M. Ter Laak, M.J. Smit, R. Kühne, H. Timmerman, R. Leurs, Mutational analysis of the antagonist-binding site of the histamine H(1) receptor, J. Biol. Chem. 274 (1999) 29994-30000.

[9] H. Sigel, R.B. Martin, Coordinating properties of the amide bond: Stability and structure of metal ion complexes of peptides and related ligands, Chem. Rev. 82 (1982) 385-426.

[10] B. Henry, J.C. Boubel, J.J. Delpuech, Carbon-13 and proton relaxation in paramagnetic complexes of aminoacids, Inorg. Chem. 25 (1986) 623-631.

[11] I. Sovago, A. Gergely, Effects of steric factors on the equilibrium and thermodynamic conditions of mixed ligand complexes of the copper(II) ion with diamines, Inorg. Chim. Acta 20 (1976) 27-32.

[12] I. Sovago, T. Kiss, A. Gergely, Effect of mixed-ligand complex formation on the ionization of the pyrrole hydrogens of histamine and histidine, J. Chem. Soc. Dalton. Trans. 8 (1978) 964-968.

[13] A. Jongejan, R. Leurs, Delineation of Receptor-Ligand Interactions at the Human Histamine H1 Receptor by a Combined Approach of Site-Directed Mutagenesis and Computational Techniques – or – How to Bind the H1 Receptor, Archiv. der. Pharmazie. 338 (2005).

[14] D. Mikulski, K. Basinski, A. Gasowska, R.B. Jarzebowska, M. Molski, L. Lomozik, Experimental and quantum-chemical studies of histamine complexes with copper(II) ion, Polyhedron. 31 (2012) 285-293.

[15] M. Bräuer, M. Kunert, E. Dinjus, M. Klubmann, M. Döring, H. Görls, E. Anders, Evaluation of the accuracy of PM3, AM1, and MNDO/d as applied to zinc compounds, J. Mol. Struct: Theochem. 505 (2000) 289-301.

[16] G. Kastas, H. Pasaoglu, B. Karabulut, Magnetic, structural and computational studies on transition metal complexes of a neurotransmitter, histamine, J. Mol. Struct. 1000 (2011) 39-48.

[17] W. Thiel, A. A Voityuk, Extension of MNDO to d orbitals: parameters and results for silicon, J. Mol. Struct: Theochem. 313 (1994) 141-154.

[18] B. Xerri, J.P. Flament, H. Petitjean, C. Berthomieu, D. Berthomieu, Vibrational Modeling of Copper-Histamine Complexes: Metal-Ligand IR ModesInvestigation, J. Phys. Chem. B. 113 (2009) 15119-15127.

[19] I. Belfilali, S. Louhibi, R. Mahboub, R. Touzani, S. El Kadiri, T. Roisnel, Study of the histamine copper(II) chloride complex catalytic activity, Res. Chem. Intermed. 39 (2015) 1819-1832.

[20] K. Senthilkumar, P. Kolandaivel, Structure, conformation and NMR studies on 1, 2-dioxane and halogen substituted 1, 2-dioxane molecules, Comp. Biol. Chem. 27 (2003) 173-183.

[21] P. Drozdzewski, E. Kordon, Isotopic studies of the metal–ligand vibrations in histamine complexes with Copper(II) Spectrochim. Acta. A 56 (2000) 1299-1304.

[22] R.G. Parr, L.V. Szentpaly, S. Liu, Electrophilicity Index, J. Am. Chem. Soc. 121 (1999) 1922-(1924).

[23] M.L. Glowka, Z. Galdecki, W. Kazimierczak, C. Maslitiski, Structure of the 1: 1 complex of histamine with copper(II) chloride, Acta. Cryst. B36 (1980) 2148-2150.

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