Combined effects of electrostatic and π-π stacking interactions: Selective binding of nucleotides and aromatic carboxylates by platinum(II)-aromatic ligand complexes

Chemistry - A European Journal

Volumn 9, Issue 14, 2003, Pages 3341-3352

  Yajima, Tatsuo ^a,b   Maccarrone, Giuseppe ^c   Takani, Masako ^d   Contino, Annalinda ^c   Arena, Giuseppe ^c   Takamido, Reiko ^b   Hanaki, Mieko ^b   Funahashi, Yasuhiro ^e   Odani, Akira ^b   Yamauchi, Osamu ^a  

^a KANSAI UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

^c UNIVERSITY OF CATANIA   (Italy)

^d KANAZAWA UNIVERSITY   (Japan)

^e NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Hydrogen bonds; Nucleotides; Platinum(II) complexes; Stability constants; Stacking interactions

Indexed keywords

AMINO ACIDS; CALORIMETRY; CRYSTAL STRUCTURE; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLATINUM COMPOUNDS; PROTONS; SYNTHESIS (CHEMICAL); THERMODYNAMICS; TITRATION; X RAY DIFFRACTION ANALYSIS;

ADDUCT FORMATIONS;

COMPLEXATION;

ALANINE; ARGININE; AROMATIC CARBOXYLIC ACID; GENTISIC ACID; GUANIDINE DERIVATIVE; GUANOSINE PHOSPHATE; INDOLEACETIC ACID; LIGAND; NUCLEOTIDE DERIVATIVE; PLATINUM;

AQUEOUS SOLUTION; ARTICLE; CALORIMETRY; COMBINATORIAL CHEMISTRY; COMPLEX FORMATION; ELECTRON TRANSPORT; HYDROGEN BOND; LIGAND BINDING; MEASUREMENT; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS; THERMODYNAMICS; X RAY DIFFRACTION;

EID: 0042415668     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304728     Document Type: Article

References (76)

1. See for example: a) E. Frieden, J. Chem. Educ. 1975, 52, 754;
2. b) A. R. Fresht, Structure and Mechanism in Protein Science, Freeman, New York, 1999;
3. c) S. K. Burley, G. A. Petsko,Adv. Protein Chem. 1988,39, 125;
4. d) B. Alberts, D. Bray, J. Lewis, M. Raff, K. Roberts, J. D. Watson, Molecular Biology of the Cell, 3rd ed., Garland, New York, 1994, pp. 89-138.
5. L. Serrano, M. Bycroft, A. R. Fersht, J. Mol. Biol. 1991, 218, 465.
6. C. A. Hunter, J. Singh, J. M. Thornton, J. Mol. Biol. 1991, 218, 837.
7. T. E. Creighton, Proteins: Structure and Molecular Properties, 2nd ed., Freeman, New York, 1993.
8. C. Branden, J. Tooze, Introduction to Protein Structure, 2nd ed., Garland Publishing, New York, 1998.
9. W. Saenger, Principles of Nucleic Acid Structure, Springer, Heidelberg, 1984.
10. See for example: a) H. B. Gray, W. R. Ellis, Jr. in Bioinorganic Chemistry (Eds.: I. Bertini, H. B. Gray, S. J. Lippard, J. S. Valentine), University Science Books, Mill Valley, 1994, pp. 315-363;
11. b) H. Pelletier, J. Kraut, Science 1992, 258, 1748;
12. c) L. Chen, R. Durley, F. S. Machews, V. L. Davidson, Science 1994, 264, 86.
13. M. Nishio, M. Hirota, Y. Umezawa, The CH/π Interactions, Wiley-VCH, New York, 1998.
14. M. Perutz, Philos. Trans. R. Soc. London Ser. A 1993, 345, 105.
15. D. A. Dougherty, Science 1996, 271, 163.
16. C. J. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303.
17. J. P. Gallivan, D. A. Dougherty, Proc. Natl. Acad. Sci. USA 1999, 96, 9459.
18. N. Zacharias, D. A. Dougherty, Trends Pharmacol. Sci. 2002, 23, 281.
19. For reviews, see for example: a) J.-M. Lehn, Science 2002, 295, 2400, and references therein; b) J.-P. Sauvage, Perspective in Supramolecular Chemistry, Vol. 5, Wiley, New York, 1999; c) M. Fujita, Struct. Bonding (Berlin) 2000, 96, 177.
20. For reviews, see for example: a) J.-M. Lehn, Science 2002, 295, 2400, and references therein; b) J.-P. Sauvage, Perspective in Supramolecular Chemistry, Vol. 5, Wiley, New York, 1999; c) M. Fujita, Struct. Bonding (Berlin) 2000, 96, 177.
21. For reviews, see for example: a) J.-M. Lehn, Science 2002, 295, 2400, and references therein; b) J.-P. Sauvage, Perspective in Supramolecular Chemistry, Vol. 5, Wiley, New York, 1999; c) M. Fujita, Struct. Bonding (Berlin) 2000, 96, 177.
22. O. Yamauchi, A. Odani, M. Takani, J. Chem. Soc. Dalton Trans. 2002, 3411.
23. K. W. Jennette, S. J. Lippard, G. A. Vassiliades, W. R. Bauer, Proc. Natl. Acad. Sci. USA 1974, 71, 3839.
24. S. J. Lippard, P. J. Bond, K. C. Wu, W. R. Bauer, Science 1976, 194, 726.
25. J. K. Barton, S. J. Lippard in Nucleic Acid-Metal ion Interactions (Ed.: T. G. Spiro), Wiley, New York, 1980, pp. 31-113.
26. J. K. Barton, A. T. Danshefsky, J. M. Goldberg, J. Am. Chem. Soc. 1984, 106, 2172.
27. J. K. Barton, Science 1986, 233, 727.
28. A. M. Pyle, J. K. Barton, Prog. Inorg. Chem. 1990, 38, 413.
29. J. K. Barton in Bioinorganic Chemistry (Eds.: I. Bertini, H. B. Gray, S. J. Lippard, J. S. Valentine), University Science Book, Mill Valley, 1994, p. 455.
30. B. Nordén, P. Lincoln, B. Åkerman, E. Tuite, Met. Ions Biol. Syst. 1996, 33, 177.
31. The following abbreviations were used: bpy, 2,2′-bipyridine; bpm, 2,2′-bipyrimidine; dpa, di(2-pyridylmethyl)amine; phen, 1,10-phenanthroline; L-Arg, L-arginine; L-Lys, L-lysine; L-Asn, L-asparginate; L-Gln, L-glutaminate; L-Ala, L-alaninate; Gly, glycinate; en, ethylenediamine; IA, indole-3-acetate; GA, gentisate; SA, salicylate; NMP, nucleotide 5′-monophosphate; AMP, adenosine 5′-monophosphate; GMP, guanosine 5′-monophosphate; CMP, cytidine 5′-monophosphate; UMP, uridine 5′-monophosphate; Ado, adenosine.
32. O. Yamauchi, A. Odani, R. Shimata, Y. Kosaka, Inorg. Chem. 1986,25, 3337.
33. A. Odani, R. Shimata, H. Masuda, O. Yamauchi, Inorg. Chem. 1991, 30, 2133.
34. A. Odani, H. Masuda, O. Yamauchi, S. Ishiguro, Inorg. Chem. 1991, 30, 4484.
35. A. Odani, T. Sekiguchi, H. Okada, S. Ishiguro, O. Yamauchi, Bull. Chem. Soc. Jpn. 1995, 68, 2093.
36. O. Yamauchi, A. Odani, H. Masuda, H. Sigel, Met. Ions Biol. Syst. 1996, 32, 207.
37. Y.-S. Wong, J. S. Lippard, J. Chem. Soc. Chem. Commun. 1977, 824.
38. H. Masuda, O. Yamauchi, Inorg. Chim. Acta 1987, 136, L29.
39. G. Brookes, L. D. Pettit, J. Chem. Soc. Dalton Trans. 1977, 1918.
40. B. E. Fischer, H. Sigel, J. Am. Chem. Soc. 1980, 102, 2998.
41. O. Yamauchi, A. Odani, J. Am. Chem. Soc. 1985, 107, 5938.
42. O. Yamauchi, A. Odani, H. Masuda, Inorg. Chim. Acta 1992, 198-200, 749.
43. H. Masuda, A. Odani, T. Yamazaki, T. Yajima, O. Yamauchi, Inorg. Chem. 1993, 32, 1111.
44. O. Yamauchi, A. Odani, S. Hirota, Bull. Chem. Soc. Jpn. 2001, 74, 1525.
45. D. M. Roundhill in Comprehensive Coordination Chemistry, Vol. 5 (Eds.: G. Wilkinson, R. D. Gillard, J. A. McCleverty), Pergamon, Oxford, 1987, Chapter 52, p. 351.
46. G. Laughlan, A. I. H. Murchie, D. G. Norman, M. H. Moore, P. C. E. Moody, D. M. J. Lilley, B. Luisi, Science 1994, 265, 520.
47. M. P. Horvath, S. C. Schultz, J. Mol. Biol. 2001, 310, 367.
48. F. A. Bovey, Nuclear Magnetic Resonance Spectroscopy, Academic Press, New York, 1969.
49. C. W. Haigh, R. B. Mallion, Org. Magn. Reson. 1972, 4, 203.
50. G. Arena, A. Contino, T. Fujimoto, D. Sciotto, Y. Aoyama, Supramol. Chem. 1999, 11, 279.
51. R. Corradini, A. Dossena, G. Impellizzeri, G. Maccarrone, R. Marchelli, E. Rizzarelli, G. Sartor, G. Vecchio, J. Am. Chem. Soc. 1994,116, 10267.
52. G. Arena, R. Calì, V. Cucinotta, S. Musumeci, E. Rizzarelli, S. Sammartano, J. Chem. Soc. Dalton Trans. 1983, 1271.
53. G. Arena, Sunner Memorial Award Lecture, Proceedings of the 44th Calorimetry Conference, Oak Ridge, Tennessee, USA, August 2, 1989, p. 84.
54. D. B. Smithrud, T. B. Wyman, F. J. Diederich, J. Am. Chem. Soc. 1991, 113, 5420.
55. M. A. Petti, T. J. Sheppod, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1988, 110, 6825.
56. R. L. Biltonen, N. Langerman, Methods Enzymol. 1979, 61, 287.
57. G. Arena, A. Casnati, A. Contino, G. G. Lombardo, D. Sciotto, R. Ungaro, Chem. Eur. J. 1999, 5, 738.
58. G. Arena, A. Casnati, A. Contino, F. G. Gulino, D. Sciotto, R. Ungaro, J. Chem. Soc. Perkin Trans. 2 2000, 419.
59. K. Aoki, J. Am. Chem. Soc. 1978, 100, 7106.
60. P. R. Mitchell, B. Prijs, H. Sigel, Helv. Chim. Acta 1979, 62, 1723.
61. K. Aoki, Met. Ions Biol. Syst. 1996, 32, 91.
62. H. Masuda, T. Sugimori, A. Odani, O. Yamauchi, Inorg. Chim. Acta 1991, 180, 73.
63. J. H. Price, A. N. Williamson, R. F. Schramm, B. B. Wayland, Inorg. Chem. 1972, 11, 1280.
64. W. D. McFadyen, L. P. G. Wakelin, I. A. G. Roos, V. A. Leopold, Med. Chem. 1985, 28, 1113.
65. J. J. Christensen, J. Ruckmann, D. J. Eatought, R. M. Izatt, Thermochim. Acta 1972, 3, 219.
66. I. Grenthe, H. Otsand, O. Ginstrupp, Acta Chem. Scand. 1970, 24, 1067.
67. M. P. Heyn, R. Bretz, Biophys. Chem. 1975, 3, 35.
68. K. H. Scheller, F. Hofstetter, P. R. Mitchell, B. Prijs, H. Sigel, J. Am. Chem. Soc. 1981, 103, 247.
69. C. Rigano, E. Rizzarelli, S. Sammartano, Thermochim. Acta 1979, 33, 211.
70. N. Walker, D. Stuart, Acta Crystallogr. Sect. A 1983, 39, 158.
71. A. Altomare, M. C. Burla, M. Camalli, M. Cascarano, C. Giacovazzo, A. Guagliardi, G. Polidori, J. Appl. Crystallogr. 1994, 27, 435.
72. C. J. Gilmore, MITHRIL, Integrated Direct Methods Computer Program, University of Glasgow, Scotland, 1990.
73. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, R. de Gelder, R. Israel, J. M. M. Smits, DIRDIF-94 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen (The Netherlands), 1994.
74. D. T. Cromer, J. T. Waber, International Tables for X-Ray Crystallography, Vol. IV, Kynoch, Birmingham, 1974.
75. D. C. Creagh, W. J. McAuley in International Tables for Crystallography, Vol. C (Ed.: A. J. C. Wilson), Kluwer Academic, Boston, 1992, pp. 219-222.
76. Crystal Structure Analysis Package, Molecular Structure Corporation, 1985 and 1999.