Rare tautomers of 1-methyluracil and 1-methylthymine: Tuning relative stabilities through coordination to PtII complexes

Chemistry - A European Journal

Volumn 15, Issue 1, 2009, Pages 209-218

  Van Der Wijst, Tushar ^a,b   Guerra, Célia Fonseca ^b   Swart, Marcel ^b,c,d   Bickelhaupt, F Matthias ^b   Lippert, Bernhard ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

^b VU UNIVERSITY AMSTERDAM   (Netherlands)

^c INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

^d UNIVERSITY OF GIRONA   (Spain)

Author keywords

Bioinorganic chemistry; Coordination complexes; Density functional calculations; Nucleobase tautomers; Platinum; Thymine; Uracil

Indexed keywords

BIOCHEMISTRY; CHEMICAL REACTIONS; COORDINATION REACTIONS; DENSITY FUNCTIONAL THEORY; DYES; LIGANDS; METAL IONS; PLATINUM; PLATINUM METALS; PROGRAMMING THEORY; SYSTEM STABILITY;

BIOINORGANIC CHEMISTRY; COORDINATION COMPLEXES; DENSITY FUNCTIONAL CALCULATIONS; NUCLEOBASE TAUTOMERS; THYMINE; URACIL;

PLATINUM COMPOUNDS;

EID: 58449107061     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801476     Document Type: Article

References (103)

1. See, for example: J. Elguero, C. Marzin, A. R. Katritzky, P. Linda, The Tautomerism of Heterocycles, Academic Press, New York, 1976.
2. a) M. Hanus, M. Kabeláč, J. Rejnek, F. Ryjáč ek, P. Hobza, J. Phys. Chem. B 2004, 108, 2087-2097;
3. b) S. A. Trygubenko, T. V. Bogdan, M. Rueda, M. Orozco, F. J. Luque, J. Šponer, P. Slavíček, P. Hobza, Phys. Chem. Chem. Phys. 2002, 4, 4192-4203;
4. c) J. Rejnek, M. Hanus, M. Kabelác, F. Ryjáček, P. Hobza, Phys. Chem. Chem. Phys. 2005, 7, 2006-2017;
5. d) M. Hanus, M. Kabelác, D. Nachtigallová, P. Hobza, Biochemistry 2005, 44, 1701-1707;
6. e) C. Colominas, F. J. Luque, M. Orozco, J. Am. Chem. Soc. 1996, 118, 6811-6821;
7. f) C. Alhambra, F. J. Luque, J. Estelrich, M. Orozco, J. Org. Chem. 1995, 60, 969-976;
8. g) J. R. Bias, F. J. Luque, M. Orozco, J. Am. Chem. Soc. 2004, 126, 154-164;
9. h) N. Russo, M. Toscano, A. Grand, J. Phys. Chem. A 2003, 107, 11533-11538;
10. i) N. Russo, M. Toscano, A. Grand, J. Phys. Chem. B 2001, 105, 4735-4741;
11. j) N. Russo, M. Toscano, A. Grand, J. Am. Chem. Soc. 2001, 123, 10272-10279;
12. k) A. M. Lamsabhi, M. Alcamí, O. Mó, M. Yáñez, ChemPhysChem 2003, 4, 1011-1016;
13. l) A. Martínez, J. Chem. Phys. 2005, 123, 024311;
14. m) M. Kabelác, P. Hobza, J. Phys. Chem. B 2006, 110, 14515-14523;
15. n) D. Kosenkov, L. Gorb, O. V. Shishkin, J. Sponer, J. Leszczynski, J. Phys. Chem. B 2008, 112, 150-157.
16. M. D. Topal, J. R. Fresco, Nature 1976, 263, 285-289.
17. J. Müller, R. K. O. Sigel, B. Lippert, J. Inorg. Biochem. 2000, 79, 261-265.
18. B. Lippert, Prog. Inorg. Chem. 2005, 54, 385-447, and references therein.
19. J. V. Burda, J. Šponer, J. Leszczynski, J. Biol. Inorg. Chem. 2000, 5, 178-188.
20. I. L. Zilberberg, V. I. Avdeev, G. M. Zhidomirov, J. Mol. Struct. (Theochem) 1997, 418, 73-81.
21. B. Lippert, H. Schöllhom, U. Thewalt, Inorg. Chim. Acta 1992, 198-200, 723-732.
22. a) F. Zamora, M. Kunsman, M. Sabat, B. Lippert, Inorg. Chem. 1997, 36, 1583-1587;
23. b) J. Šponer, J. E. Sponer, L. Gorb, J. Leszczynski, B. Lippert, J. Phys. Chem. A 1999, 103, 11406-11413;
24. c) D. V. Deubel, J. Am. Chem. Soc. 2008, 130, 665-675;
25. d) M. Kang, H. T. Chifotides, K. R. Dunbar, Biochemistry 2008, 47, 2265-2276;
26. e) A. C. G. Hotze, M. E. T. Broekhuisen, A. H. Velders, K. van der Schilden, J. G. Haasnoot, J. Reedijk, Eur. J. Inorg. Chem. 2002, 369-376.
27. a) G. Frommer, I. Mutikainen, F. J. Pesch, E. C. Hillgeris, H. Preut, B. Lippert, Inorg. Chem. 1992, 31, 2429-2434;
28. b) D. B. Pedersen, B. Simard, A. Martinez, A. Moussatova, J. Phys. Chem. A 2003, 107, 6464-6469.
29. a) B. Lippert, H. Schöllhorn, U. Thewalt, J. Am. Chem. Soc. 1986, 108, 6616-6621;
30. b) F. Pichierri, D. Holthenrich, E. Zangrando, B. Lippert, L. Randaccio, J. Biol. Inorg. Chem. 1996, 1, 439-445;
31. c) J. Müller, E. Zangrando, N. Pahlke, E. Freisinger, L. Randaccio, B. Lippert, Chem. Eur. J. 1998, 4, 397-405;
32. d) P. J. Sanz Miguel, P. Lax, M. Willermann, B. Lippert, Inorg. Chim. Acta 2004, 357, 4552-4561.
33. a) H. Schöllhom, U. Thewalt, B. Lippert, J. Am. Chem. Soc. 1989, 111, 7213-7221;
34. b) F. Zamora, H. Witkowski, E. Freisinger, J. Müller, B. Thormann, A. Albinati, B. Lippert, J. Chem. Soc. Dalton Trans. 1999, 175-182.
35. a) B. Lippert, Inorg. Chim. Acta 1981, 55, 5-14;
36. b) O. Renn, B. Lippert, A. Albinati, Inorg. Chim. Acta 1991, 190, 285-289;
37. c) I. Mutikainen, O. Renn, B Lippert, unpublished results.
38. a) W. Brüning, E. Freisinger, M. Sabat, R. K. O. Sigel, B. Lippert, Chem. Eur. J. 2002, 8, 4681-4692;
39. b) W. Brüning, I. Ascaso, E. Freisinger, M. Sabat, B. Lippert, Inorg. Chim. Acta 2002, 339, 400-410.
40. a) B. Lippert, J. Raman Spectrosc. 1980, 9, 324-333;
41. b) R. Pfab, P. Jandik, B. Lippert, Inorg. Chim. Acta 1982, 66, 193-204;
42. c) I. Escorihuela, L. R. Falvello, M. Tomás, E. P. Urriolabeitia, Cryst. Growth Des. 2004, 4, 655-657.
43. D. Gupta, M. Huelsekopf, M. Morell Cerdà, R. Ludwig, B. Lippert, Inorg. Chem. 2004, 43, 3386-3393.
44. a) M. Swart, C. Fonseca Guerra, F. M. Bickelhaupt, J. Am. Chem. Soc. 2004, 126, 16718-16719;
45. b) C. Fonseca Guerra, F. M. Bickelhaupt, Angew. Chem. 1999, 111, 3120-3122;
46. Angew. Chem. Int. Ed. 1999, 38, 2942-2945;
47. c) C. Fonseca Guerra, F. M. Bickelhaupt, J. G. Snijders, E. J. Baerends, J. Am. Chem. Soc. 2000, 122, 4117-4128;
48. d) C. Fonseca Guerra, F. M. Bickelhaupt, E. J. Baerends, Cryst. Growth Des. 2002, 2, 239-245.
49. a) C. Fonseca Guerra, F. M. Bickelhaupt, Angew. Chem. 2002, 114, 2194-2197;
50. Angew. Chem. Int. Ed. 2002, 41, 2092-2095;
51. b) C. Fonseca Guerra, F. M. Bickelhaupt, J. Chem. Phys. 2003, 119, 4262-4273.
52. C. Fonseca Guerra, F. M. Bickelhaupt, S. Saha, F. Wang, J. Phys. Chem. A 2006, 110, 4012-4020.
53. See, for example: G. T. de Jong, F. M. Bickelhaupt, J. Chem. Theory Comput. 2006, 2, 322-335.
54. a) J. K.-C. Lau, D. V. Deubel, J. Chem. Theory Comput. 2006, 2, 103-106;
55. b) J. V. Burda, M. Zeizinger, J. Leszczynski, J. Comput. Chem. 2005, 26, 907-914;
56. c) J. Raber, C. Zhu, L. A. Eriksson, Mol. Phys. 2004, 102, 2537-2544.
57. ADF2006.01, SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands, http://www.scm.com. E. J Baerends, J. Autschbach, A. Bérces, C. Bo, P. M Boerrigter, L. Cavallo, D. P. Chong, L. Deng, R. M. Dickson, D. E. Ellis, L. Fan, T. H. Fischer, C. Fonseca Guerra, S. J. A. van Gisbergen, J. A. Groeneveld, O. V. Gritsenko, M. Grüning, F. E. Harris, P. van den Hoek, H. Jacobsen, G. van Kessel, F. Kootstra, E. van Lenthe, D. A. McCormack, V. P. Osinga, S. Patchkovskii, P. H. T. Philipsen, D. Post, C. C. Pye, W. Ravenek, P. Ros, P. R. T. Schipper, G. Schreckenbach, J. G. Snijders, M. Solà, M. Swart, D. Swerhone, G. te Velde, P. Vernooijs, L. Versluis, O. Visser, E. van Wezenbeek, G Wiesenekker, S. K. Wolff, T. K. Woo, T. Ziegler.
58. a) G. te Velde, F. M. Bickelhaupt, E. J. Baerends, C. Fonseca Guerra, S. J. A. van Gisbergen, J. G. Snijders, T. Ziegler, J. Comput. Chem. 2001, 22, 931-967;
59. b) C. Fonseca Guerra, O. Visser, J. G. Snijders, G. te Velde, E. J. Baerends, in Methods and Techniques for Computational Chemistry, (Eds.: E. Clementi, G. Corongiu), STEF: Cagliari, 1995, pp. 305-395;
60. c) E. J. Baerends, D. E. Ellis, P. Ros, Chem. Phys. 1973, 2, 41-51;
61. d) E. J. Baerends, P. Ros, Chem. Phys. 1975, 8, 412-418;
62. e) E. J. Baerends, P. Ros, Int. J. Quantum Chem. Symp. 1978, 12, 169-190;
63. f) C. Fonseca Guerra, J. G. Snijders, G. te Velde, E. J. Baerends, Theor. Chem. Acc. 1998, 99, 391-403;
64. g) P. M. Boerrigter, G. te Velde, E. J. Baerends, Int. J. Quantum Chem. 1988, 33, 87-113;
65. h) G. te Velde, E. J. Baerends, J. Comp. Physiol. 1992, 99, 84-98;
66. i) J. G. Snijders, P. Vernooijs, E. J. Baerends, At. Nucl. Data Tables 1981, 26, 483-509;
67. j) J. Krijn, E. J. Baerends, Fit-Functions in the HFS-Method; Internai Report (In Dutch), Vrije Universiteit, Amsterdam, 1984;
68. k) L. Versluis, T. Ziegler, J. Chem. Phys. 1988, 88, 322-328;
69. l) J. C. Slater, Quantum Theory of Molecules and Solids, Vol. 4, McGraw-Hill, New York, 1974;
70. m) A. D. Becke, J. Chem. Phys. 1986, 84, 4524-4529;
71. n) A. D Becke, Phys. Rev. A 1988, 38, 3098-3100;
72. o) S. H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200-1211;
73. p) J. P. Perdew, Fortschr. Phys. 1986, 33, 8822-8824 (Erratum: Phys. Rev. B 1986, 34, 7406);
74. q) L. Fan, T. Ziegler, J. Chem. Phys. 1991, 94, 6057-6063.
75. a) M. Swart, F. M. Bickelhaupt, Int. J. Quantum Chem. 2006, 106, 2536-2544;
76. b) M. Swart, F. M. Bickelhaupt, J. Comput. Chem. 2008, 29, 724-734.
77. a) A. Bérces, R. M. Dickson, L. Fan, H. Jacobsen, D. Swerhone, T. Ziegler, Comput. Phys. Commun. 1997, 100, 247-262;
78. b) H. Jacobsen, A. Bérces, D. Swerhone, T. Ziegler, Comput. Phys. Commun. 1997, 100, 263-276;
79. c) S. K. Wolff, Int. J. Quantum Chem. 2005, 104, 645-659.
80. E. van Lenthe, E. J. Baerends, J. G. Snijders, J. Chem. Phys. 1994, 101, 9783-9792.
81. a) A. Klamt, G. Schüürmann, J. Chem. Soc. Perkin Trans. 2 1993, 799-805;
82. b) A. Klamt, J. Phys. Chem. 1995, 99, 2224-2235;
83. C. C. Pye, T. Ziegler, Theor. Chem. Acc. 1999, 101, 396-408.
84. M. Swart, E. Rösler, F. M. Bickelhaupt, Eur. J. Inorg. Chem. 2007, 3646-3654.
85. J. L. Miller, P. A. Kollman, J. Phys. Chem. 1996, 100, 8587.
86. C. Fonseca Guerra, E. J. Baerends, F. M. Bickelhaupt, Cent. Eur. J. Chem. 2008, 6, 15-21.
87. D. V. Deubel, J. Am. Chem. Soc. 2002, 124, 5834-5842.
88. B. Lippert, Prog. Inorg. Chem. 1989, 37, 1-97.
89. a) B. Lippert in Cisplatin-Chemistry and Biochemistry of a Leading Anticancer Drug (Ed.: B. Lippert), VHCA Zürich, 1999, pp. 379-403;
90. b) M.-A. Elizondo-Riojas, F. Gonnet, J.-C. Chottard, J.-P. Girault, J. Kozelka, J. Biol. Inorg. Chem. 1998, 3, 30-43;
91. c) J. Vinje, E. Sletten, J. Kozelka, Chem. Eur. J. 2005, 11, 3863-3871.
92. H. Rauter, E. C. Hillgeris, A. Erxleben, B. Lippert, J. Am. Chem. Soc. 1994, 116, 616-624.
93. C. F. Moreno-Luque, E. Freisinger, B. Costisella, R. Griesser, J. Ochocki, B. Lippert, H. Sigel, J. Chem. Soc. Perkin Trans. 2 2001, 2005-2011.
94. B. Lippert, Chem. Biodiversity 2008, 5, 1455-1474.
95. R. B. Martin in Cisplatin-Chemistry and Biochemistry of a Leading Anticancer Drug (Ed.: B. Lippert), VHCA Zürich, 1999, pp. 183-205.
96. Migration may proceed via an N,O-chelate. For a relevant structure, see: J. Ruiz, M. D. Villa, V. Rodríguez, N. Cutillas, C. Vicente, G. López, D. Bautista, Inorg. Chem. 2007, 46, 5448-5449.
97. See, for example: L. Holland, W.-Z. Shen, W. Micklitz, B. Lippert, Inorg. Chem. 2007, 46, 11356-11365.
98. See, for example: a) G. J. Narlikar, D. Herschlag, Annu. Rev. Biochem. 1997, 66, 19-59;
99. b) P. C. Bevilacqua, T. S. Brown, S.-i. Nakano, R. Yajima, Biopolymers 2004, 73, 90-109;
100. c) E. M. Moody, J. T. J. Lecomte, P. C. Bevilacqua, RNA 2005, 11, 157-172.
101. a) H. Louro, M. J. Silva, M. G. Boavida, Environ. Mol. Mutagen. 2002, 40, 283-291;
102. b) L. J. N. Bradley, K. J. Yarema, S. J. Lippard, J. M. Essigmann, Biochemistry 1993, 32, 982-988;
103. c) M. J. Pillaire, J. S. Hoffmann, M. Defais, G. Villani, Biochimie 1995, 77, 803-807.