Co-ordinating properties of cyclopeptides. Thermodynamic and spectroscopic study on the formation of copper(II) complexes with cyclo(Gly-His)4 and cyclo(Gly-His-Gly)2 and their superoxide dismutase-like activity
Co-ordinating properties of cyclopeptides. Thermodynamic and spectroscopic study on the formation of copper(II) complexes with cyclo(Gly-His)4 and cyclo(Gly-His-Gly)2 and their superoxide dismutase-like activity(452 views) Bonomo RP, Impellizzeri G, Pappalardo G, Purrello R, Rizzarelli E, Tabbì G
Journal Of The Chemical Society Dalton Transactions (ISSN: 0300-9246), 1998; (22): 3851-3857.
Affiliations: Department of Chemical Sciences, University of Catania, Viale A. Doria 6, 95125 Catania, Italy
Istituto per lo Studio delle Sostanze Naturali di Interesse Alimentare e Chimico-Farmaceutico, Sezione per lo Studio di Modelli di Metallo-Enzimi, Viale A. Doria 6, 95125 Catania, Italy
References: Beyer, W.F., Fridovich, I., Mullenbach, G.T., Hallewell, R., (1988) Oxy-Radicals in Molecular Biology and Pathology, pp. 145-162. , eds. P. A. Cerutti, I. Fridovich and J. M. McCord, Alan R. Liss Inc., New Yor
Hernandez, L.A., Crisham, M.B., Granger, D.N., (1987) Biology of Copper Complexes, pp. 201-214. , ed. J. R. J. Sorenson, Humana Press, Clifton, NJ
Reed, G.A., Madhu, C., Biology of Copper Complexes, pp. 287-298
Okuyama, S., Hashimoto, S., Aihara, H., Willingham, W., Sorenson, J.R.J., Biology of Copper Complexes, pp. 301-313
Sorenson, J.R.J., (1987) Biology of Copper Complexes, pp. 243-257. , ed. J. R. J. Sorenson, Humana Press, Clifton, NJ
Linder, M.C., (1991) Biochemistry of Copper, , ed. E. Frieden, Plenum, New York and London, ch. 9
Cass, A.E.G., (1985) Metalloproteins. Part 1: Metalloproteins with Redox Roles, pp. 121-156. , ed. P. Harrison, MacMillan, London
Kendrick, M.J., May, M.T., Plishka, M.J., Robinson, K.D., (1992) Metals in Biological Systems, p. 162. , Ellis Horwood, New York
Costanzo, L.L., De Guidi, G., Giuffrida, S., Rizzarelli, E., Vecchio, G., (1993) J. Inorg. Biochem., 50, p. 273
Condorelli, G., Costanzo, L.L., De Guidi, G., Giuffrida, S., Rizzarelli, E., Vecchio, G., (1994) J. Inorg. Biochem., 54, p. 257
Bonomo, R.P., Conte, E., Impellizzeri, G., Pappalardo, G., Purrello, R., Rizzarelli, E., (1996) J. Chem. Soc., Dalton Trans., p. 3093
Bonomo, R.P., Impellizzeri, G., Pappalardo, G., Rizzarelli, E., (1990) Magnetic Resonance in Medicine and Biology, 4, pp. 239-244. , eds. A. Agnoli and F. Conti, Centro Tecnochimico, Padova
Chelli, M., Ginanneschi, M., Papini, A.M., Pinzani, D., Rapi, G., Borghi, E., Laschi, F., Occhiuzzi, M., (1993) J. Chem Res., p. 437. , S M
Kubota, S., Tsi Yang, J., (1994) Proc. Natl. Acad. Sci. USA, 81, p. 3283
Le Nguyen, D., Castro, B., (1987) Peptide Chem., p. 231
Touchstone, J.C., Dobbins, M.F., (1983) Practice of Thin Layer Chromatography, p. 180. , Wiley-Interscience, New York
Arena, G., Rigano, C., Rizzarelli, E., Sammartano, S., (1979) Talanta, 26, p. 1
Gans, P., Vacca, A., Sabatini, A., (1985) J. Chem. Soc., Dalton Trans., p. 1195
Maggiore, R., Musumeci, S., Sammartano, S., (1976) Talanta, 23, p. 43
Lund, A., Vanngard, T., (1969) J. Chem. Phys., 50, p. 2979
Bond, A.M., (1980) Modern Polarographic Methods in Analytical Chemistry, pp. 182-190. , Marcel Dekker, New York and Basel
Nervi, C., personal communicationBard, A.J., (1980) Electrochemical Methods: Fundamentals and Applications, p. 430. , Wiley, New York
Sawyer, D.T., Roberts, J.L., (1974) Experimental Electrochemistry for Chemists, p. 42. , Wiley, New York
Beyer, W. F., Fridovich, I., Mullenbach, G. T., Hallewell, R., (1988) Oxy-Radicals in Molecular Biology and Pathology, pp. 145-162. , eds. P. A. Cerutti, I. Fridovich and J. M. McCord, Alan R. Liss Inc., New Yor
Hernandez, L. A., Crisham, M. B., Granger, D. N., (1987) Biology of Copper Complexes, pp. 201-214. , ed. J. R. J. Sorenson, Humana Press, Clifton, NJ
Reed, G. A., Madhu, C., Biology of Copper Complexes, pp. 287-298
Linder, M. C., (1991) Biochemistry of Copper, , ed. E. Frieden, Plenum, New York and London, ch. 9
Cass, A. E. G., (1985) Metalloproteins. Part 1: Metalloproteins with Redox Roles, pp. 121-156. , ed. P. Harrison, MacMillan, London
Kendrick, M. J., May, M. T., Plishka, M. J., Robinson, K. D., (1992) Metals in Biological Systems, p. 162. , Ellis Horwood, New York
Costanzo, L. L., De Guidi, G., Giuffrida, S., Rizzarelli, E., Vecchio, G., (1993) J. Inorg. Biochem., 50, p. 273
Bonomo, R. P., Conte, E., Impellizzeri, G., Pappalardo, G., Purrello, R., Rizzarelli, E., (1996) J. Chem. Soc., Dalton Trans., p. 3093
Bonomo, R. P., Impellizzeri, G., Pappalardo, G., Rizzarelli, E., (1990) Magnetic Resonance in Medicine and Biology, 4, pp. 239-244. , eds. A. Agnoli and F. Conti, Centro Tecnochimico, Padova
Bhirud, R. G., Srivastava, T. S., (1991) Inorg. Chim. Acta, 179, p. 125
Bonomo, R. P., Bonsignore, F., Conte, E., Impellizzeri, G., Pappalardo, G., Purrello, R., Rizzarelli, E., (1993) J. Chem. Soc., Dalton Trans., p. 1295
Pierre, J. L., Chautemps, P., Refaif, S., Beguin, C., El Marzouki, A., Serratrice, G., Saint-Aman, E., Rey, P., (1995) J. Am. Chem. Soc., 117, p. 1965
James, B. R., Williams, R. J. P., (1961) J. Chem. Soc., p. 2007
Bonomo, R. P., Riggi, F., Di Bilio, A. J., (1988) Inorg. Chem., 27, p. 2510
Bonomo, R. P., Casella, L., Di Gioia, L., Molinari, H., Impellizzeri, G., Jordan, T., Pappalardo, G., Rizzarelli, E., (1997) J. Chem. Soc., Dalton Trans., p. 2387
Azab, H. A., Banci, L., Borsari, M., Luchinat, C., Sola, M., Viezzoli, M. S., (1992) Inorg. Chem., 31, p. 4649
Greenwood, N. N., Earnshaw, A., (1987) Chemistry of the Elements, p. 1371. , Pergamon, Oxford
Bonomo, R. P., Marchelli, R., Tabbi, G., (1995) J. Inorg. Biochem., 60, p. 205
Touchstone, J. C., Dobbins, M. F., (1983) Practice of Thin Layer Chromatography, p. 180. , Wiley-Interscience, New York
Bond, A. M., (1980) Modern Polarographic Methods in Analytical Chemistry, pp. 182-190. , Marcel Dekker, New York and Basel
Sawyer, D. T., Roberts, J. L., (1974) Experimental Electrochemistry for Chemists, p. 42. , Wiley, New York
Co-ordinating properties of cyclopeptides. Thermodynamic and spectroscopic study on the formation of copper(II) complexes with cyclo(Gly-His)4 and cyclo(Gly-His-Gly)2 and their superoxide dismutase-like activity
Two cyclopeptides, cyclo(Gly-His)4 and cyclo(Gly-His-Gly)2 were synthesized with the specific aim to form copper(II) complexes which are able to mimic the active site of superoxide dismutase. Proton and copper(II) complexes were thermodynamically characterized. The copper(II) complexes were also studied by means of optical and ESR spectroscopy to gain information on their structural features and by voltammetry to know about their redox ability. Moreover, the antioxidant activity of these complex species was tested against enzymatically generated superoxide radical. Depending on the pH value of the solution, definite complexes could be characterized, in particular [Cu{cyclo(Gly-His)4}]2+ and [Cu{cyclo(Gly-His)4}H-2] and [Cu{cyclo(Gly-His-Gly)2}H-2] are the main species, which were taken into consideration to assay their antioxidant catalytic activity. The ESR studies suggested that a four-nitrogen co-ordination by means of imidazole nitrogen atoms or deprotonated peptide nitrogen atoms forms the environment around copper. At the same co-ordination level, the redox properties of these compounds parallel their scavenging abilities against O2 - which are lower than those of other copper(II) complexes previously tested. The [Cu{cyclo(Gly-His)4}]2+ complex showed higher redox potential and better catalytic ability than [Cu{cyclo(Gly-His)4}H-2] and [Cu{cyclo(Gly-His-Gly)2}H-2], which have roughly similar redox potentials and scavenging abilities.
Co-ordinating properties of cyclopeptides. Thermodynamic and spectroscopic study on the formation of copper(II) complexes with cyclo(Gly-His)4 and cyclo(Gly-His-Gly)2 and their superoxide dismutase-like activity
Co-ordinating properties of cyclopeptides. Thermodynamic and spectroscopic study on the formation of copper(II) complexes with cyclo(Gly-His)4 and cyclo(Gly-His-Gly)2 and their superoxide dismutase-like activity
Kállay C, Dávid A, Timári S, Nagy EM, Sanna D, Garribba E, Micera G, De Bona P, Pappalardo G, Rizzarelli E, Sóvágó I * Copper(II) complexes of rat amylin fragments(357 views) Dalton T (ISSN: 1477-9234, 1477-9226, 1477-9234electronic), 2011 Oct 14; 40(38): 9711-9721. Impact Factor:3.838 ViewExport to BibTeXExport to EndNote