Intrinsic acid-base properties of purine derivatives in aqueous solution and comparison of the acidifying effects of platinum(II) coordinated to N1 or N7: Acidifying effects are reciprocal and the proton "outruns" divalent metal ions

Inorganic Chemistry

Volumn 42, Issue 1, 2003, Pages 32-41

  Griesser, Rolf ^a   Kampf, Gunnar ^a,b   Kapinos, Larisa E ^a   Komeda, Seiji ^c   Lippert, Bernhard ^b   Reedijk, Jan ^c   Sigel, Helmut ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b TU DORTMUND UNIVERSITY   (Germany)

^c LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

9 ETHYLGUANINE; 9 METHYLADENINE; 9 METHYLHYPOXANTHINE; ADENINE DERIVATIVE; GUANINE DERIVATIVE; HYPOXANTHINE DERIVATIVE; INOSINE; LIGAND; METAL ION; N6',N6',N9 TRIMETHYLADENINE; PLATINUM; PROTON; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ACID BASE BALANCE; ACIDIFICATION; AQUEOUS SOLUTION; ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; PH; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS;

EID: 0037237146     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic020535o     Document Type: Article

References (61)

1. 2+ is located.
2. Sigel, H.; Lippert, B. Pure Appl. Chem. 1998, 70, 845-854.
3. Song, B.; Zhao, J.; Griesser, R.; Meiser, C.; Sigel, H.; Lippert, B. Chem. - Eur. J. 1999, 5, 2374-2387.
4. Sponer, J. E.; Leszczynski, J.; Glahé, F.; Lippert, B.; Šponer, J. Inorg. Chem. 2001, 40, 3269-3278.
5. (a) Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug; Lippert, B., Ed.; VHCA, Zürich, Wiley-VCH: Weinheim, Germany, 1999; pp 1-563.
6. (b) Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy; Pinedo, H. M., Schomagel Schornagel, J. H., Eds.; Plenum Press: New York, 1996; pp 1-357.
7. (a) Interactions of Metal Ions with Nucleotides, Nucleic Acids, and Their Constituents; Metal Ions in Biological Systems 32; Sigel, A., Sigel, H., Eds.; M. Dekker, Inc.: New York, Basel, 1996; pp 1-814.
8. (b) Probing of Nucleic Acids by Metal Ion Complexes of Small Molecules; Metal Ions in Biological Systems 33; Sigel, A., Sigel, H., Eds.; M. Dekker, Inc.: New York, Basel, 1996; pp 1-678.
9. (c) Guo, Z.; Sadler, P. J. Angew. Chem., Int. Ed. 1999, 38, 1512-1531.
10. (d) Guo. Z.; Sadler, P. J. Adv. Inorg. Chem. 2000, 49, 183-306.
11. (a) Reedijk, J. Chem. Commun. 1996, 801-806.
12. (b) Bloemink, M. J.; Reedijk, J. Met. Ions Biol. Syst. 1996, 32, 641-685.
13. (a) Sigel, H.; Song, B.; Oswald, G.; Lippert, B. Chem. - Eur. J. 1998, 4, 1053-1060.
14. (b) Lüth, M. S.; Song, B.; Lippert, B.; Sigel, H. Inorg. Chem. 2000, 39, 1305-1310.
15. (a) Lippert, B. Met. Ions Biol. Syst. 1996, 33, 105-141.
16. (b) Lippert, B. J. Chem. Soc., Dalton Trans. 1997, 3971-3976.
17. (c) Sigel, R. K. O.; Thompson, S. M.; Freisinger, E.; Lippert, B. Chem. - Eur. J. 2001, 7, 1968-1980.
18. (a) Takahara. P. M.; Frederick, C. A.; Lippard, S. J. J. Am. Chem. Soc. 1996, 118, 12309-12321.
19. (b) Whitehead, J. P.; Lippard, S. J. Met. Ions Biol. Syst. 1996, 32, 687-726.
20. (a) Marzilli, L. G.; Saad, J. S.; Kuklenyik, Z.; Keating, K. A.; Xu, Y. J. Am. Chem. Soc. 2001, 123, 2764-2770.
21. (b) Sullivan, S. T.; Saad, J. S.; Fanizzi, F. P.; Marzilli, L. G. J. Am. Chem. Soc. 2002, 124, 1558-1559.
22. Scheller, K. H.; Scheller-Krattiger, V.; Martin, R. B. J. Am. Chem. Soc. 1981, 103, 6833-6839.
23. Beyerle-Pfnür, R.; Brown, B.; Faggiani, R.; Lippert, B.; Lock, C. J. L. Inorg. Chem. 1985, 24, 4001-4009.
24. van der Veer, J. L.; van den Elst, H.; Reedijk, J. Inorg. Chem. 1987, 26, 1536-1540.
25. Arpalahti, J.; Lehikoinen, P. Inorg. Chem. 1990, 29, 2564-2567.
26. Rau, T.; van Eldik, R. Met. Ions Biol. Syst. 1996, 32. 339-378.
27. Martin, R. B. Met. Ions Biol. Syst. 1979, 9, 1-39.
28. Song, B.; Sigel, R. K. O.; Sigel, H. Chem. - Eur. J. 1997, 3, 29-33.
29. Kampf, G.; Kapinos, L. E.; Griesser, R.; Lippert, B.; Sigel, H. J. Chem. Soc., Perkin Trans. 2 2002, 1320- 1327.
30. Blindauer, C. A.; Hollý, A.; Dvořaková, H.; Sigel, H. J. Chem. Soc., Perkin Trans. 2 1997. 2353-2363.
31. den Hartog, J. H. J.; Salm, M. L.; Reedijk, J. Inorg. Chem. 1984, 23, 2001-2005.
32. Raudaschl-Sieber, G.; Schöllhorn, H.; Thewalt, U.; Lippert, B. J. Am. Chem. Soc. 1985, 107, 3591-3595.
33. Beyerle-Pfnür, R. Ph.D. Thesis, 1985. Universität München, 1985, See also ref 13.
34. Meiser, C.; Song, B.; Freisinger, E.; Peilert, M.; Sigel, H.; Lippert, B. Chem. - Eur. J. 1997, 3, 388-398.
35. Sigel, H. Pure Appl. Chem. 1999, 71. 1727-1740.
36. Glasoe, P. K.; Long, F. A. J. Phys. Chem. 1960, 64, 188-190.
37. Tribolet, R.; Sigel, H. Eur. J. Biochem. 1987, 163, 353-363.
38. Martin, R. B. Science 1963, 139, 1198-1203.
39. Paul, M. A.; Long, F. A. Chem. Rev. 1957, 57, 1-45.
40. Song, B.; Oswald, G.; Bastian, M.; Sigel, H.; Lippert, B. Met.-Based Drugs 1996, 3, 131-141.
41. Benoit, R. L.; Fréchette, M. Can. J. Chem. 1984, 62, 995-1000.
42. Benoit, R. L.; Fréchette, M. Can. J. Chem. 1985, 63, 3053-3056.
43. Martin, R. B. Met. Ions Biol. Syst. 1996, 32, 61-89.
44. Sigel, H.; Zuberbühler, A. D.; Yamauchi, O. Anal. Chim. Acta 1991, 255, 63-72.
45. Corfú, N. A.; Sigel, H. Eur. J. Biochem. 1991, 199, 659-669.
46. An exception seems to be the first value in the final column of entry 5c in Table 1, which appears to be too high; the reason for this is at present not clear.
47. Lemaire, D.; Fouchet, M.-H.; Kozelka, J. J. Inorg. Biochem. 1994, 53, 261-271. See Table S1 in their Supporting Information.
48. Sigel, H. Coord. Chem. Rev. 1995, 144, 287-319.
49. Sigel, H. J. Indian Chem. Soc. 1997, 74, 261-271 (P. Ray Award Lecture).
50. Binary complexes: (a) Blindauer, C. A.; Emwas, A. H.; Holý, A.; Dvořáková, H.; Sletten, E.; Sigel, H. Chem. - Eur. J. 1997, 3, 1526-1536.
51. (b) Blindauer, C. A.; Holý, A.; Dvořáková, H.; Sigel, H. J. Biol. Inorg. Chem. 1998, 3, 423-433.
52. (c) Gómez-Coca, R. B.; Kapinos, L. E.; Holý, A.; Vilaplana, R. A.; González-Vílchez, F.; Sigel, H. J. Chem. Soc., Dalton Trans. 2000, 2077-2084.
53. Ternary complexes: (a) Gómez-Coca, R. B.; Kapinos, L. E.; Holý, A.; Vilaplana, R. A.; González-Vílchez, F.; Sigel, H. J. lnorg J. Inorg. Biochem. 2001, 84, 39-46.
54. (b) Gómez-Coca, R. B.; Kapinos, L. E.; Holý, A.; Vilaplana, R. A.; González-Vílchez, F.; Sigel, H. Met.-Based Drugs 2000, 7, 313-324.
55. Sigel, H.; Chen, D.; Corfú, N. A.; Gregfáň, F.; Holý, A.; Strašák, M. Helv. Chim. Acta 1992, 75, 2634-2656.
56. Kampf, G.; Lüth, M. S.; Müller, J.; Holý, A.; Lippert, B.; Sigel, H. Z. Naturforsch. 2000, 55b, 1141-1152.
57. Kampf, G.; Lüth, M. S.; Kapinos, L. E.; Müller, J.; Holý, A.; Lippert, B.; Sigel, H. Chem. - Eur. J. 2001, 7, 1899-1908.
58. Bastian, M.; Sigel, H. J. Coord. Chem. 1991, 23, 137-154.
59. Martin, R. B. J. Am. Chem. Soc. 1967, 89, 2501-2502.
60. Noszál, B.; Scheller-Krattiger, V.; Martin, R. B. J. Am. Chem. Soc. 1982, 104, 1078-1081.
61. See page 84 in ref 33.