Abstract
The interaction of diethyltin(IV), DET, with selected bioligands having a variety of model functional groups was investigated at 25 °C and ionic strength 0.1 mol·dm−3 NaCl using the potentiometric technique. The hydrolysis constants of the DET cation and the formation constants of the complexes formed in solution were calculated using the MINIQUAD-75 program. The stoichiometry and stability constants for the complexes formed are reported. The results show the formation of 1:1 and 1:2 complexes with amino acids and DNA constituents. The dicarboxylic acids form 1:1 complexes. The peptides form both 110 complexes and the corresponding deprotonated amide species [Et2Sn(LH−1)] (11-1). The participation of different ligand functional groups in binding to organotin is discussed. The concentration distributions of the various complex species were evaluated as a function of pH. The standard thermodynamic parameters ΔH° and ΔS°, calculated from the temperature dependence of the equilibrium constants, were investigated for the interaction of DET with thymine as a representative example of DNA constituents. The effect of ionic strength and solvent on hydrolysis constants of DET, protonation equilibria of thymine and its complex formation with DET were investigated and discussed.
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Rosenberg, B., Van Camp, L., Trasko, J.E., Mansour, V.H.: Platinum compounds: a new class of potent antitumour agent. Nature 222, 385–386 (1969)
Gielen, M., Lelieveld, P., de Vos, D., Willem, R.: In: Keppler, K. (ed.) Metal Complexes in Cancer Chemotherapy, p. 383. VCH, Weinheim (1993)
Barbieri, R.: QSAR approach to understand antitumor activity of organotin. Inorg. Chim. Acta 191, 253–259 (1991)
Penninks, A.H., Bol-Schoenmakers, M., Seinen, W.: Cellular interaction of organotin compounds in relation to their antitumour activity In: Gielen, M. (ed.) Tin-Based Antitumour Drugs. NATO ASI Series, vol. H37, p. 169. Springer, Berlin (1990)
Crowe, A.J.: Tin Compounds and Their Potential as Pharmaceutical Agents, Tin-Based Antitumour Drugs. NATO ASI Series, vol. H37, p. 69. Springer, Berlin (1990)
Gielen, M.: Organotin compounds and their therapeutic potential. Appl. Organomet. Chem. 16, 481–494 (2002)
Crowe, A.J., Smith, P.J., Cordin, C.J., Parge, H.E., Smith, F.E.: Possible pre-dissociation of diorganotin dihalide complexes: relationship between antitumour activity and structure. Cancer Lett. 24, 45–48 (1984)
El-Sherif, A.A., Shoukry, M.M.: Ternary copper(II) complexes involving 2-(aminomethyl)-benzimidazole and some bio-relevant ligands. Equilibrium studies and kinetics of hydrolysis for glycinemethyl ester under complex formation. Inorg. Chim. Acta 360, 473–487 (2007)
El-Sherif, A.A., Jeragh, B.: Mixed ligand complexes of Cu(II)–2-(2-pyridyl)-benzimidazole and aliphatic or aromatic dicarboxylic acids: synthesis, characterization and biological activity. J. Spectochim. Acta A 68, 877–882 (2007)
El-Sherif, A.A.: Mixed-ligand complexes of 2-(aminomethyl)benzimidazole palladium(II) with various biologically relevant ligands. J. Solution Chem. 35, 1287–1301 (2006)
El-Sherif, A.A.: Synthesis, spectroscopic characterization, and biological activity on newly synthesized copper(II) and nickel(II) complexes incorporating bidentate oxygen–nitrogen hydrazone ligands. Inorg. Chim. Acta 362, 4991–5000 (2009)
El-Sherif, A.A.: Synthesis, solution equilibria and antibacterial activity of Co(II) with 2-(aminomethyl)-benzimidazole and dicarboxylic acids. J. Solution Chem. 39, 1562–1581 (2010)
El-Sherif, A.A.: Coordination properties of bidentate (N, O) and tridentate (N, O, O) heterocyclic alcohols with dimethyltin(IV) ion. J. Coord. Chem. 64(7), 1240–1253 (2011)
El-Sherif, A.A., Shoukry, M.M.: Synthesis, characterization, potentiometric and thermodynamics of dimethyltin(IV)2+ cation with 4-amino-6-hydroxy-2-mercapto pyrimidine (AHMP). J. Main Group Met. Chem. 29, 189–200 (2006)
El-Sherif, A.A.: Solution coordination chemistry of organotin(IV) cations with bio-relevant ligands. J. Solution Chem. 41, 1522–1554 (2012)
Van Uitert, G.L., Hass, C.G.: Studies on the coordination compounds. A method for determining thermodynamic equilibrium constants in mixed solvents. J. Am. Chem. Soc. 75, 451–455 (1971)
Gans, P., Sabatini, A., Vacca, A.: An improved computer program for the computation of formation constants from potentiometric data. Inorg. Chim. Acta 18, 237–239 (1976)
Pettit, L.: Personal communication. University of Leeds
Mohamed, M.M.A., Shoukry, M.M.: Interaction of diphenyltin(IV) dichloride with some selected bioligands. Chem. Pharm. Bull. 49, 253–257 (2001)
Dey, D.K., Dey, S.P., Lycka, A., Rosair, G.M.: Structure and spectroscopy of diorganotin(IV) complexes derived from N′-(2-hydroxy-3-methoxybenzylidene)benzohydrazide. Polyhedron 30, 2544–2549 (2011)
Dey, D., Basu Baul, T.S., Rivarola, E.: A convenient synthesis and structural assessment of [Sn(CH3)2(L2)](ClO4)2. Bull. Chem. Soc. Jpn. 66, 1556–1558 (1993)
Natusch, D.F.S., Porter, L.J.: Direct detection of Hg(II)-thio-ether bonding in complexes of methionine and S-methylcysteine by 1H-NMR nuclear magnetic resonance. J. Chem. Soc. Chem. Commun. 15, 596 (1970)
Ali, M.A., Mirza, A.H., Chartres, J.D., Bernhardt, P.V.: Synthesis, characterization and X-ray crystal structures of seven-coordinate pentagonal–bipyramidal zinc(II), cadmium(II) and tin(IV) complexes of a pentadentate N3S2 thiosemicarbazone. Polyhedron 30, 299–306 (2011)
El-Sherif, A.A.: Chapter 4, Coordination chemistry of palladium(II) ternary complexes with relevant biomolecules. In: Stoichiometry and Research. The Importance of Quantity in Biomedicine, pp. 79–120. In-Tech Publisher, Rijeka (2012)
El-Sherif, A.A., Shoukry, M.M., Khairy, E.M.: Ternary complexes involving copper(II) and amino acids, peptides and DNA constituents. The kinetics of hydrolysis of α-amino acid esters. Transition Met. Chem. 27, 656–664 (2002)
El-Sherif, A.A., Shoukry, M.M., El-Bahnasawy, R.M., Ahmed, D.M.: Complex formation reactions of palladium(II)-1,3-diaminopropane with various biologically relevant ligands. Kinetics of hydrolysis of glycine methyl ester through complex formation. Cent. Eur. J. Chem. 8, 919–927 (2010)
Surdy, P., Rubini, P., Buzás, N., Henry, B., Pellerito, L., Gajda, T.: Interaction of dimethyltin(IV)2+ cation with Gly–Gly, Gly–His, and some related ligands. A new case of a metal ion able to promote peptide nitrogen deprotonation in aqueous solution. Inorg. Chem. 38, 346–352 (1999)
Mohamed, M.M.A.: Complex formation reactions of divinyltin(IV) complexes with amino acids, peptides, dicarboxylic acids and related compounds. J. Coord. Chem. 56, 747–759 (2003)
Al-Najjar, A.A., Mohamed, M.M.A., Shoukry, M.M.: Interaction of dipropyltin(IV) with amino acids, peptides, dicarboxylic acids and DNA constituents. J. Coord. Chem. 59, 193–206 (2006)
Martin, R.B., Mariam, Y.H.: Interactions between metal ions and nucleic base, nucleosides and nucleotides in solution. In: Siegel, H., Siegel, A. (eds.) Metal Ions in Biological Systems, vol. 8, pp. 57–124. Marcel Dekker, Inc., New York (1979)
Noszol, B., Scheller-Krattiger, V., Martin, R.B.: A unified view of carbon bound hydrogen exchange of H(2) in imidazoles and H(8) in purine nucleosides and their metal ion complexes. J. Am. Chem. Soc. 104, 1078–1081 (1982)
Jardetzky, O., Pappas, P., Waide, N.G.: Proton magnetic resonance studies of purine and pyrimidine derivatives. IX. The protonation of pyrimidines in acid solution. J. Am. Chem. Soc. 85, 1657–1658 (1963)
Roberts, B.W., Lambert, J.B., Roberts, J.D.: Nitrogen-15 magnetic resonance spectroscopy. VI. Pyrimidine derivatives. J. Am. Chem. Soc. 87, 5439–5441 (1965)
Kramer-Schnabel, U., Linder, P.W.: Substituent effects in the protonation and complexation with copper(II) ions of organic monophosphate esters. A potentiometric and calorimetric study. Inorg. Chem. 30, 1248–1254 (1991)
Rees, D.C.: Experimental evaluation of the effective dielectric constant of proteins. J. Mol. Biol. 141, 323–326 (1980)
Rogersa, N.K., Mooreb, G.R., Sternberga, M.J.E.: Electrostatic interactions in globular proteins: calculation of the pH dependence of the redox potential of cytochrome C551. J. Mol. Biol. 182, 613–616 (1985)
Akerlof, G., Short, O.A.: The dielectric constant of dioxane–water mixtures between 0 and 80 correction. J. Am. Chem. Soc. 75, 6357–6362 (1953)
Mohamed, M.M.A., Shehata, M.R., Shoukry, M.M.: Trimethyltin(IV) complexes with some selected DNA constituents. J. Coord. Chem. 53, 125–142 (2001)
El-Sherif, A.A.: Mixed ligand complex formation reactions and equilibrium studies of Cu(II) with bidentate heterocyclic alcohol (N, O) and some bio-relevant ligands. J. Solution Chem. 39, 131–150 (2010)
Nasanen, R., Ekman, A.: Potentiometric and spectrophotometric studies on 8-quinolinol and its derivatives. V. Ionization of 8-quinolinol-5-sulfonic acid and 7-iodo-8-quinolinol-5-sulfonic acid in aqueous solution. Acta Chem. Scand. 6, 1384–1390 (1952)
Aljahdali, M., Foti, C., El-Sherif, A.A., Mohamed, M.M.A., Soliman, A.A., Al Ruqi, O.S.: Potentiometric determination of stability constants and thermodynamic data for dimethyltin(IV)dichloride complexes with imino-bis(methyl phosphonic acid) in water and dioxane–water mixtures. Monatsh. Chem. 144, 1467–1480 (2013)
Bernhard, S.A.: Chap. 8: The Structure and Function of Enzymes. W.A. Benjamin, New York (1986)
Gajda-Schrantz, K., Nagy, L., Fiore, T., Pellerito, L., Gajda, T.: Equilibrium and spectroscopic studies of diethyltin(IV) complexes formed with hydroxymono- and dicarboxylic acids and their thioanalogues. J. Chem. Soc., Dalton Trans. 152–159 (2002)
Blunden, S.J., Chapman, A.: In: P.J. Craig (ed.) Organometallic Compounds in the Environment, p. 111. Longman, Harlow, Essex (1986), and refs. therein
Arakawa, Y., Wada, O.: In: Siegel, H., Siegel, A. (eds.) Metal Ions in Biological Systems, vol. 29, p. 101. Marcel Dekker, New York (1993), and refs. therein
De Stefano, C., Foti, C., Gianguzza, A., Sammartano, S.: In: A. Gianguzza, E. Pelizzetti, S. Sammartano (eds.) Chemical Processes in Marine Environments, p. 213. Springer, Berlin (2000), and refs. therein
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Aljahdali, M.S., Abdelkarim, A.T. & El-Sherif, A.A. Potentiometry, Stability and Thermodynamics of Diethyltin(IV) Dichloride with Some Selected Biomolecules. J Solution Chem 42, 2240–2266 (2013). https://doi.org/10.1007/s10953-013-0104-9
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DOI: https://doi.org/10.1007/s10953-013-0104-9