Abstract
The known organotin(IV) complexes with 2-mercaptopyrimidine (L) [Me2SnL2] (1), [Bun 2SnL2] (2), [Ph2SnL2] (3), and [Ph3SnL] (4) were synthesized using a new approach. The effect of the synthesized compounds on peroxidation of fatty acids (oleic and linoleic) was studied. Complexes 1–4 promote the peroxidation of oleic acid. Their effect on the enzymatic peroxidation of linoleic acid with lipoxygenase was compared with that of cisplatin and in vitro cytoxicity against sarcoma cancer cells was determined. The antiproliferative effect of complexes 2–4 was demonstrated.
Similar content being viewed by others
References
A. G. Davis, Organotin Chemistry, Ed. P. J. Smith, VCH, Weinheim (Germany), 1997.
Chemistry of Tin, Blackie Academic and Professional, London (UK), 1998.
L. Pellerito and L. Nagy, Coord. Chem. Rev., 2002, 224, 111.
K. Cain, M. D. Partis, and D. E. Griffiths, Biochem. J., 1977, 166, 593; (b) B. G. Farrow and A. P. Dawson, Eur. J. Biochem., 1978, 86, 85.
M. Gielen, Coord. Chem. Rev., 1996, 151, 41; (b) M. Gielen and E. R. T. Tiekink, in Metallotherapeutic Drugs and Metal-Based Diagnostic Agents. The Use of Metals in Medicine, Eds M. Gielen and E. R. T. Tiekink, J. Wiley and Sons, New York, 2005.
M. Nath, S. Pokharia, and R. Yadav, Coord. Chem. Rev., 2001, 215, 99.
M. Nath, S. Pokharia, X. Song, G. Eng, M. Gielen, M. Kemmer, M. Biesemans, R. Willem, and D. de Vos, Appl. Organomet. Chem., 2003, 17, 305 and references therein.
J. J. Roberts and J. M. Pascoe, Nature; 1972, 235, 282; (b) D. R. Williams, Educ. Chem., 1974, 11, 124.
L. Ghys, M. Biesemans, M. Gielen, A. Garoufis, N. Hadjiliadis, R. Willem, and J. C. Martins, Eur. J. Inorg. Chem., 2000, 513; (b) Z. Yang, T. Bakas, A. Sanchez-Diaz, K. Charalabopoulos, J. Tsangaris, and N. Hadjiliadis, J. Inorg. Biochem., 1998, 72, 133.
M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, E. R. Milaeva, Yu. A. Gracheva, V. Yu. Tyurin, N. Kourkoumelis, K. C. Christoforidis, A. K. Metsios, S. Karkabounas, and K. Charalabopoulos, Eur. J. Med. Chem., 2007, in press (doi: 10.1016/j.ejmech.2007.03.028).
B. Samuelsson, S. E. Dahlen, J. Lindgren, C. A. Rouzer, and C. N. Serhan, Science, 1987, 237, 1171; (b) M. J. Knapp and J. P. Klinman, Biochemistry, 2003, 42, 11466.
S. Zha, V. Yegnasubramanian, W. G. Nelson, W. B. Isaacs, and A. M. De Marzo, Cancer Lett., 2004, 215, 1; (b) M. Kreich and P. Claus, Angew. Chem., Int. Ed., 2005, 44, 7800.
S. K. Hadjikakou, M. A. Demertzis, M. Kubicki, and D. Kovala-Demertzi, Appl. Organomet. Chem., 2000, 14, 727 and reference therein; (b) R. Schmiedgen, F. Huber, A. Silvestri, G. Ruisi, M Rossi, and R. Barbieri, Appl. Organomet. Chem., 1998, 12, 861 and references therein; (c) L. Petrilli, F. Caruso, and E. Rivarola, Main Group Met. Chem., 1994, 17, 439; (d) D. Kovala-Demertzi, P. Tauridou, J. M. Tsangaris, and A. Moukarika, Main Group Met. Chem., 1993, 16, 315.
A. Evangelou, S. Karkabounas, G. Kalpouzos, M. Malamas, R. Liasko, D. Stefanou, A. T. Vlahos, and T. A. Kabanos, Cancer Lett., 1997, 119, 221.
M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, M. Kubicki, S. Skoulika, T. Bakas, M. Baril, and I. S. Butler, Inorg Chem, 2007, 46, 1187.
J. Shamir, P. Starostin, and V. Peruzzo, J. Raman Spectr., 1994, 25, 251; (b) H. Jankovics, C. Pettinari, F. Marchetti, E. Kamu, L. Nagy, S. Troyanov, and L. Pellerito, J. Inorg. Biochem., 2003, 97, 370; (c) E. García Martínez, A. Sánchez Gonzáles, J. S. Casas, J. Sordo, G. Valle, and U. Russo, J. Organomet. Chem., 1993, 453, 47.
Organic Peroxides, Eds E. Niki and W. Ando, J. Wiley, New York, 1992; (b) E. Milaeva, V. Petrosyan, N. Berberova, Y. Pimenov, and L. Pellerito, Bioinorg. Chem. Appl., 2004, 2, 69.
M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, M. Kubicki, S. Karkabounas, K. Charalabopoulos, N. Kourkoumelis, and T. Bakas, J. Organomet. Chem., 2006, 691, 1780; (b) I. H. Segel, Biochemical Calculations, 2nd ed. J. Wiley and Sons, New York, 1976.
(a) M. A. Thompson, ArgusLab, Planaria Software, Seattle (WA 98155); (b) Protein Data Bank, http: //www.rcsb.org/ pdb/; (c) R. Wang, L. Lai, and S. Wang, J. Comp. Aided Mol. Design, 2002, 16, 11; (d) J. J. P. Stewart, J. Comput. Chem., 1989}, 10, 209
Author information
Authors and Affiliations
Corresponding authors
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 737–743, April, 2007.
Rights and permissions
About this article
Cite this article
Xanthopoulou, M.N., Hadjikakou, S.K., Hadjiliadis, N. et al. Biological studies of organotin(IV) complexes with 2-mercaptopyrimidine. Russ Chem Bull 56, 767–773 (2007). https://doi.org/10.1007/s11172-007-0115-z
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-007-0115-z