Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Kinetic Studies on the Reactions of [(TLtBu)PtCl]+ and [Pt(tpdm)Cl]+ Complexes with Some Thiols and Thioethers

Enisa Selimović A , Biljana Petrović A , Dragan Čanović B , Živadin D. Bugarčić A and Jovana Bogojeski A C

A Department of Chemistry, Faculty of Science, University of Kragujevac, R. Domanovića 12, PO Box 60, 34000 Kragujevac, Serbia.

B Faculty of Medicine, University of Kragujevac, S. Markovića 69, 34000 Kragujevac, Serbia.

C Corresponding author. Email: jrosic@kg.ac.rs

Australian Journal of Chemistry 66(5) 534-538 http://dx.doi.org/10.1071/CH12218
Submitted: 25 April 2012  Accepted: 13 December 2012   Published: 31 January 2013

Abstract

Substitution reactions of the complexes [(TLtBu)PtCl]+ and [Pt(tpdm)Cl]+, where TLtBu = 2,6-bis[(1,3-di-tert-butylimidazolin-2-imino)methyl]pyridine and tpdm = terpyridinedimethane, with nucleophiles: S-methyl-L-cysteine (S-Met-L-Cys), L-cysteine (L-Cys), glutathione (GSH) and L-methionine (L-Met) were studied in aqueous 0.1 M NaClO4 solution in the presence of 10 mM NaCl using variable-temperature UV-vis spectrophotometry. The higher reactivity of the complex with the tpdm ligand could be attributed to the influence of the bulkiness of the tert-butyl-groups from the [(TLtBu)PtCl]+ complex. The order of reactivity of the studied ligands is: S-Met-L-Cys > L-Met > GSH > L-Cys. The thioethers (S-Met-L-Cys and L-Met) are more reactive than the thiols (GSH and L-Cys). This order of reactivity is in relation with their electron properties and structures. The negative values reported for the entropy of activation confirmed the associative mode.

Graphical Abstract Image


References

[1]  E. Alessio, in Bioinorganic Medicinal Chemistry (Ed. E. Alessio) 2011, Ch. 1–4 (John Wiley & Sons Inc.: New York, NY).

[2]  J. Reedijk, Pure Appl. Chem. 2011, 83, 1709.
         | CrossRef | 1:CAS:528:DC%2BC3MXhs1Gqt7bP&md5=bf42acd93bdeecc0d652578dde82e155CAS | open url image1

[3]  J. Reedijk, Macromol. Symp. 2008, 270, 193.
         | CrossRef | 1:CAS:528:DC%2BD1cXht1ekt7%2FO&md5=4b97976fa3b72547019c85e55304a9baCAS | open url image1

[4]  M. A. Jakupec, M. Galanski, B. K. Keppler, Rev. Phys. Biochem. Pharm. 2003, 146, 1.
         | CrossRef | 1:CAS:528:DC%2BD3sXltlKitrY%3D&md5=889cbf47afc279f546e0a96f5a4310c1CAS | open url image1

[5]  M. A. Jakupec, M. Galanski, B. K. Keppler, Met. Ions Biol. Syst. 2004, 42, 179.
         | 1:CAS:528:DC%2BD2cXmtFGgur4%3D&md5=168e7d68d1d3c2c07fbcf95f52198f97CAS | open url image1

[6]  E. Volckova, L. P. Dudones, R. N. Bose, Pharm. Res. 2002, 19, 124.
         | CrossRef | 1:CAS:528:DC%2BD38XitVSmu7s%3D&md5=6da8fcdf8d1d8e1e614a02ada252de30CAS | open url image1

[7]  B. Petrović, Ž. D. Bugarčić, Aust. J. Chem. 2005, 58, 544.
         | CrossRef | open url image1

[8]  T. Soldatović, Ž. D. Bugarčić, J. Inorg. Biochem. 2005, 99, 1472.
         | CrossRef | open url image1

[9]  Ž. D. Bugarčić, J. Rosić, B. Petrović, N. Summa, R. Puchta, R. van Eldik, J. Biol. Inorg. Chem. 2007, 12, 1141.
         | CrossRef | open url image1

[10]  B. Petrović, Ž. D. Bugarčić, J. Coord. Chem. 2001, 53, 35.
         | CrossRef | open url image1

[11]  B. Petrović, Ž. D. Bugarčić, A. Dees, I. Ivanović-Burmazović, F. Heinemann, R. Puchta, R. van Eldik, Inorg. Chem. 2012, 51, 1516.
         | CrossRef | open url image1

[12]  J. Reedijk, Chem. Rev. 1999, 99, 2499.
         | CrossRef | 1:CAS:528:DyaK1MXlt12rsb8%3D&md5=8fbfe5295e7327f721db6b91ffb20d82CAS | open url image1

[13]  B. Lippert, in Cisplatin, Chemistry and Biochemistry of Leading Antitumor Drugs (Ed. B. Lippert) 1999, pp. 183–221 (Wiley-VCH: Zurich).

[14]  J. Bogojeski, Ž. D. Bugarčić, R. Puchta, R. van Eldik, Eur. J. Inorg. Chem. 2010, 5439.
         | CrossRef | 1:CAS:528:DC%2BC3cXhsVyrsb3F&md5=01c40bb15292f6bc47efea7638b9e60cCAS | open url image1

[15]  M. Đurović, J. Bogojeski, B. Petrović, D. Petrović, F. W. Heinemann, Ž. D. Bugarčić, Polyhedron 2012, 41, 70.
         | CrossRef | open url image1

[16]  J. Bogojeski, R. Jelić, D. Petrović, E. Herdtweck, P. G. Jones, M. Tamm, Ž. D. Bugarčić, Dalton Trans. 2011, 40, 6515.
         | CrossRef | 1:CAS:528:DC%2BC3MXntFGhsb8%3D&md5=bf0c5f1cc0ce7fbc3d2c1fd7b5a40d47CAS | open url image1

[17]  A. Mijatović, J. Bogojeski, B. Petrović, Ž. D. Bugarčić, Inorg. Chim. Acta 2012, 383, 300.
         | CrossRef | open url image1

[18]  M. L. Tobe, J. Burgess, in Inorganic Reaction Mechanism (Eds M. L. Tobe, J. Burgess) 1999, p. 70, p. 364 (Longman: London).

[19]  G. Annibale, L. Cattalini, L. Canovese, G. Michelon, G. Marangoni, M. L. Tobe, Inorg. Chem. 1983, 22, 975.
         | CrossRef | 1:CAS:528:DyaL3sXhsFShsrY%3D&md5=8f2113d62f9a9627f7cebee27b504cbaCAS | open url image1

[20]  T. Shi, L. I. Elding, Inorg. Chem. 1996, 35, 735.
         | CrossRef | 1:CAS:528:DyaK28XjtFygsA%3D%3D&md5=582eac7d7a91ee4f5a9b685a2fdecaeeCAS | open url image1

[21]  Ž. D. Bugarčić, F. W. Heinemann, R. van Eldik, Dalton Trans. 2004, 279.
         | CrossRef | open url image1

[22]  Ž. D. Bugarčić, B. V. Đorđević, Monatsh. Chem. 1998, 129, 1267. open url image1

[23]  Ž. D. Bugarčić, G. Liehr, R. van Eldik, J. Chem. Soc., Dalton Trans. 2002, 951.
         | CrossRef | open url image1

[24]  J. M. Teuben, M. Rodrugez, I. Zubiri, J. Reedijk, J. Chem. Soc., Dalton Trans. 2000, 369.
         | CrossRef | 1:CAS:528:DC%2BD3cXms1Ghtg%3D%3D&md5=6200221a38e31871967001f7812447b5CAS | open url image1

[25]  V. Vasić, M. Čakar, J. Savić, B. Petrović, J. Nadeljković, Ž. D. Bugarčić, Polyhedron 2003, 22, 279.
         | CrossRef | open url image1

[26]  A. Hofmann, D. Jaganyi, O. Q. Munro, G. Liehr, R. Van Eldik, Inorg. Chem. 2003, 42, 1688.
         | CrossRef | 1:CAS:528:DC%2BD3sXnt1SgsQ%3D%3D&md5=07cec9164c5d9a16b895f525a3880fa3CAS | open url image1

[27]  D. Petrović, L. M. R. Hill, P. G. Jones, W. B. Tolman, M. Tamm, Dalton Trans. 2008, 887.
         | CrossRef | open url image1

[28]  A. N. Vedernikov, J. C. Huffman, K. G. Caulton, Inorg. Chem. 2002, 41, 6244.
         | CrossRef | 1:CAS:528:DC%2BD38Xot1Krt78%3D&md5=a67e29dd629f48bf08cf44df6c2c841dCAS | open url image1

[29]  T. G. Appleton, J. R. Hall, S. F. Ralph, C. S. M. Thompson, Inorg. Chem. 1984, 23, 3514.
         | CrossRef | 1:CAS:528:DyaL2cXlvValt7g%3D&md5=ae3d8e492925f3ea1f9e69c317c24298CAS | open url image1



Supplementary MaterialSupplementary Material 31.8 KB Export Citation