Potentiometric and spectroscopic evidence for co-ordination of dimethyltin(IV) to phosphate groups of DNA fragments and related ligands

Abstract

The co-ordination of dimethyltin(IV) to 5′-GMP, 5′-ATP and 5′-d(CGCGCG)₂ and to their sugar constituents (D-ribose and 2-deoxy-D-ribose) was investigated in aqueous solution by means of potentiometric titration and ¹H and ³¹P NMR spectroscopic methods. The results showed that in acidic media the phosphate groups can provide suitable sites for metal ion co-ordination, while the hydroxy groups of the sugars or the sugar moieties of the two nucleotides play a role in this process at higher pH. The base moieties of 5′-GMP and 5′-ATP were not co-ordinated to dimethyltin(IV). The stability constants of the complexes formed in the above systems were determined by pH-metric titration. The data revealed a stronger co-ordination ability of the triphosphate as compared with that of the monophosphate. The comparison of the stability constants of the D-ribose and 2-deoxy-D-ribose complexes showed that more stable species were formed when neighbouring alcoholic hydroxy groups were available for co-ordination. The observed chemical shift changes of the ³¹P NMR resonances, as compared with those measured for the metal-free systems, demonstrated that the phosphate groups of the DNA fragment 5′-d(CGCGCG)₂ chains act as binding sites for dimethyltin(IV) between pH 4.5 and 7. The 1- and 2-D ¹H NMR spectra indicated that the base and sugar moieties do not participate in the co-ordination process under these conditions.

References

1. A. K. Saxena and F. Huber, Coord. Chem. Rev., 1989, 95, 109; M. Gielen, Main Group Metal Chem, 1994, 17, 1.
2. A. J. Crowe, P. J. Smith and G. Atassi, Chem. Biol. Interact., 1980, 32, 171; R. Barbieri, L. Pellerito, G. Ruisi, M. T. Lo Guidice, F. Huber and G. Attasi, Inorg. Chim. Acta, 1982, 66, 139; M. Takahashi, F. Furukawa, T. Kobuko, Y. Kurata and Y. Hayashi, Cancer Lett., 1983, 20, 271; G. Ruisi, A. Silvestri, M. T. Lo Guidice, R. Barbieri, G. Attasi, F. Huber, K. Gratz and L. Lamartina, J. Inorg. Biochem., 1985, 25, 229.
3. A. J. Crowe, P. J. Smith, C. J. Cardin, H. E. Parge and F. E. Smith, Cancer Lett., 1984, 24, 45.
4. W. Stillwell and H. C. Winter, Biochem. Biophys. Res. Commun., 1974, 56, 617.
5. R. Barbieri, A. Silvestri, A. M. Giuliani, V. Piro, F. Di Simone and G. Madonia, J. Chem. Soc., Dalton Trans., 1992, 585; R. Barbieri, G. Ruisi, A. Silvestri, A. M. Giuliani, A. Barbieri, G. Spina, F. Pieralli and F. Del Giallo, J. Chem. Soc., Dalton Trans., 1995, 467; Q. Li, P. Yang, H. Wang and M. Guo, J. Inorg. Biochem., 1996, 64, 181.
6. (a) G. Arena, R. Cali, A. Contino, N. Loretta, S. Musumeci and R. Purello, J. Chem. Soc., Dalton Trans., 1992, 2039; (b) R. Barbieri, A. Silvestri and V. Piro, J. Chem. Soc., Dalton Trans., 1990, 3605; (c) R. Barbieri, G. Alonzo and R. H. Herber, J. Chem. Soc., Dalton Trans., 1987, 789; (d) C. J. Cardin and A. Roy, Inorg. Chim. Acta, 1985, 107, 57; (e) G. Ruisi, M. T. Lo Guidice and L. Pellerito, Inorg. Chim. Acta, 1984, 93, 161.
7. L. Nagy, L. Korecz, I. Kiricsi, L. Zsikla and K. Burger, Struct. Chem., 1991, 2, 231.
8. K. Burger, L. Nagy, N. Buzás, A. Vértes and H. Mehner, J. Chem. Soc., Dalton Trans., 1993, 2499; L. Nagy, H. Mehner, A. A. Christy, E. Sletten, F. T. Edelmann and Q. M. Andersen, J. Radioanal. Nucl. Chem., 1988, 227, 89.
9. A. Vértes, K. Sümegh, E. Kuzmann, K. Burger, L. Nagy, K. Schrantz and N. Buzás, J. Radioanal. Nucl. Chem., 1996, 203, 399.
10. N. Buzás, M. A. Pujar, L. Nagy, E. Kuzmann, A. Vértes and H. Mehner, J. Radioanal. Nucl. Chem., Lett., 1995, 189, 237.
11. N. Buzás, B. Gyurcsik, L. Nagy, X.-x. Zhang, L. Korecz and K. Burger, Inorg. Chim. Acta, 1994, 218, 65.
12. L. Nagy, B. Gyurcsik, K. Burger, S. Yamashita, T. Yamaguchi, H. Wakita and M. Nomura, Inorg. Chim. Acta, 1995, 230, 105.
13. B. Gyurcsik, N. Buzás, T. Gajda, L. Nagy, E. Kuzmann, A. Vértes and K. Burger, Z. Naturforsch., Teil B, 1995, 5, 515.
14. N. Buzás, T. Gajda, E. Kuzmann, L. Nagy, A. Vértes and K. Burger, Main Group Met. Chem., 1995, 18, 633.
15. N. Buzás, T. Gajda, L. Nagy, E. Kuzmann, A. Vértes and K. Burger, Inorg. Chim. Acta, 1998, 274, 167.
16. M. Piotto, V. Saudek and V. Sklenar, J. Biomol. NMR 2, 1992, 661; V. Sklenar, M. Piotto, R. Leppik and V. Saude, J. Magn. Reson., Ser. A, 1993, 102, 241.
17. R. S. Tobias and M. Yasuda, Can. J. Chem., 1964, 42, 781.
18. G. Arena, R. Purrello, E. Rizzarelli, A. Gianguzza and L. Pellerito, J. Chem. Soc., Dalton Trans., 1989, 773.
19. T. Natsume, S.-i. Aizawa, K. Hatano and S. Funahashi, J. Chem. Soc., Dalton Trans., 1994, 2749.
20. (a) K. Burger and L. Nagy, in Biocoordination Chemistry; Metal Complexes of Carbohydrates and Sugar-type Ligands, ed. K. Burger, Ellis Horwood, Chichester, 1990, ch. VI, p. 236; (b) R. M. Izatt, J. H. Rytting, L. D. Hansen and J. J. Christensen, J. Am. Chem. Soc., 1966, 88, 2641.
21. C. P. Rao, K. Geetha and M. S. S. Raghavan, Biometals, 1994, 7, 25; K. Geetha, M. S. Ranghava, S. K. Kulshreshtha, R. Sasikala and C. P. Rao, Carbohydr. Res., 1995, 271, 163; R. P. Bandwar, M. Giralt, J. Hidalgo and C. P. Rao, Carbohydr. Res., 1996, 284, 73; R. P. Bandwar and C. P. Rao, Carbohydr. Res., 1994, 264, 227; P. Klüfers and J. Schuhmacher, Angew. Chem., Int. Ed. Engl., 1994, 33, 1742, 1863; R. Fusch, N. Habermann and P. Klüfers, Angew Chem., Int. Ed. Engl., 1993, 32, 852; J. Burger and P. Klüfers, Z. Anorg. Allg. Chem., 1996, 622, 1740; L. Nagy, T. Yamaguci, T. Páli, M. Nomura and H. Ohtaki, ACH, Models in Chemistry, 1998, 135, 129.
22. L. Pellerito, G. Ruisi, R. Barbieri and M. T. Lo Giudice, Inorg. Chim. Acta, 1977, 21, L33.
23. See for example, H. Sigel, Chem. Soc. Rev., 1993, 22, 255; H. Sigel and B. Song, in Metal Ions in Biological Systems, eds. A. Sigel and H. Sigel, Marcel Dekker, New York, 1966, vol. 32, p. 136.
24. (a) H. Sigel, S. S. Massoud and N. A. Corfu, J. Am. Chem. Soc., 1994, 116, 1958; (b) H. Sigel, R. Tribolet, R. Malini-Balakrishnan and B. R. Martin, Inorg. Chem., 1987, 26, 2149.
25. Y. J. Chao and D. R. Kearns, J. Am. Chem. Soc., 1977, 99, 6425.
26. T. Yamaguchi, L. Nagy, M. Nomura and H. Ohtaki, Photon Factory Activity Report, 1989, 7, 82; L. Palladino, S. Della Longa, A. Reale, M. Belli, A. Scafati, G. Onari and A. Santucci, J. Chem. Phys., 1993, 98, 2720.
27. W. S. Sheldrick, Acta Crystallogr., Sect. B, 1981, 37, 1820.
28. P. Klüfers and P. Mayer, Z. Anorg. Allg. Chem., 1997, 623, 1496.
29. R. D. Izatt, J. J. Christensen and J. H. Rytting, Chem. Rev., 1971, 71, 5.
30. (a) K. Atkári, T. Kiss, R. Bertani and B. R. Martin, Inorg. Chem., 1996, 35, 7089; (b) T. Kiss, I. Sóvágó and B. R. Martin, Inorg. Chem., 1991, 30, 2130.
31. N. A. Froystein and E. Sletten, Acta Chem. Scand., 1991, 45, 219; N. A. Froystein, J. T. Davis, B. R. Reid and E. Sletten, Acta Chem. Scand., 1993, 47, 649.
32. S. Steinkopf, A. Garoufis, W. Nerdal and E. Sletten, Acta Chem. Scand., 1995, 49, 495; Q. Xu, R. K. Shoemaker and W. Braunlin, Biophys. J., 1993, 65, 1039.
33. W. H. Braunlin, Advances in Biophysical Chemistry, ed. A. C. Bush, Jai Press, New Delhi, 1995, vol. 5, p. 89.
34. G. Lamm and G. R. Pack, Proc. Natl. Acad. Sci. U.S.A., 1990, 87, 9033.