Selective and efficient recognition of thymidylylthymidine (TpT) by bis(ZnII-cyclen) and thymidylylthymidylylthymidine (TpTpT) by tris(ZnII-cyclen) at neutral pH in aqueous solution

Chemistry - A European Journal

Volumn 5, Issue 11, 1999, Pages 3113-3123

  Kimura, Eiichi ^a   Kikuchi, Motoya ^a   Kitamura, Hideyuki ^a   Koike, Tohru ^a  

^a HIROSHIMA UNIV SCHOOL OF MEDICINE   (Japan)

Author keywords

Macrocyclic ligands; Molecular recognition; Nucleotides; Thymidine; Zinc

Indexed keywords

NUCLEOTIDE; THYMIDINE DERIVATIVE; ZINC;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PH; STOICHIOMETRY; TITRIMETRY;

EID: 0032703229     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19991105)5:11<3113::AID-CHEM3113>3.0.CO;2-L     Document Type: Article

References (58)

1. a) Molecular Basis of Specificity in Nucleic Acid-Drug Interactions (Eds.: B. Pullman, J. Jortner), Kluwer Academic, London, 1990;
2. b) Bioorganic Chemistry: Nucleic Acids (Ed.: S. M. Hecht), Oxford University Press, Oxford, 1996.
3. a) B. H. Geierstanger, D. E. Wemmer, Annu. Rev. Biophys. Biomol. Struct. 1995, 24, 436-493;
4. b) E. T. Kool, Chem. Rev. 1997, 97, 1473-1487;
5. c) C. S. Chow, F. M. Bogdan, Chem. Rev. 1997, 97, 1489-1513;
6. d) D. G. Gorenstein, Chem. Rev. 1994, 94, 1315-1338.
7. a) R. A. Manderville, J. F. Ellena, S. M. Hecht, J. Am. Chem. Soc. 1995, 117, 7891-7903;
8. b) J. Stubbe, J. W. Kozarich, Chem. Rev. 1987, 87, 1107-1136;
9. c) A. M. Calafat, H. Won, L. G. Marzilli, J. Am. Chem. Soc. 1997, 119, 3656-3664.
10. a) M. L. Kopka, C. Yoon, D. Goodsell, P. Pjura, R. E. Dickerson, J. Mol. Biol. 1985, 183, 553-563;
11. b) M. Coll, C. A. Frederick, A. H.-J. Wang, A. Rich, Proc. Natl. Acad. Sci. USA 1987, 84, 8385-8389;
12. c) J. G. Pelton, D. E. Wemmer, J. Am. Chem. Soc. 1990, 112, 1393-1399;
13. d) E. L. Fish, M. J. Lane, J. N. Vournakis, Biochemistry 1988, 27, 6026-6032.
14. a) S. Kamitori, F. Takusagawa, J. Mol. Biol. 1992, 225, 445-456;
15. b) C. Lian, H. Robinson, A. H.-J. Wang, J. Am. Chem. Soc. 1996, 118, 8791-8801.
16. a) J. M. Gottesfeld, L. Neely, J. W. Trauger, E. E. Baird, P. B. Dervan, Nature 1997, 387, 202-205;
17. b) C. M. Nunn, S. Neidle, J. Med. Chem. 1995, 38, 2317-2325;
18. c) N. T. Thuong, C. Hélène, Angew. Chem. 1993, 105, 697-723; Angew. Chem. Int. Ed. Engl. 1993, 32, 666-690.
19. c) N. T. Thuong, C. Hélène, Angew. Chem. 1993, 105, 697-723; Angew. Chem. Int. Ed. Engl. 1993, 32, 666-690.
20. a) R. S. Lokey, Y. Kwok, V. Guelev, C. J. Pursell, L. H. Hurley, B. L. Iverson, J. Am. Chem. Soc. 1997, 119, 7202-7210;
21. b) A. Slama-Schwork, M.-P. Teulade-Fichou, J.-P. Vigneron, E. Taillandier, J.-M. Lehn, J. Am. Chem. Soc. 1995, 117, 6822-6830.
22. For interaction of metal ions or complexes with nucleic acid constituents, see: a) Metal Ions in Biological Systems, Vol. 32 and 33 (Eds.: A. Sigel, H. Sigel), Mercel Dekker, New York, 1996;
23. b) M. Iwamoto, S. Mukundan, L. G. Marzilli, J. Am. Chem. Soc. 1994, 116, 6238-6244;
24. c) P. M. Takahara, A. C. Rosenzweig, C. A. Frederic, S. J. Lippard, Nature 1995, 377, 649-652;
25. d) B. A. Jackson, J. K. Barton, J. Am. Chem. Soc. 1997, 119, 12986-12987;
26. e) O. Krizanovic, M. Sabat, R. Beyerle-Pfnür, B. Lippert, J. Am. Chem. Soc. 1993, 115, 5538-5548.
27. a) E. Kimura, Progress in Inorganic Chemistry, Vol. 41 (Ed.: K. D. Karlin), Wiley, New York, 1994, pp. 443-491;
28. b) E. Kimura, T. Koike, Advances in Inorganic Chemistry, Vol. 44 (Ed.: A. G. Sykes), Academic Press, New York, 1997, pp. 229-261;
29. c) E. Kimura, T. Koike, M. Shionoya, Structure and Bonding: Metal Site in Proteins and Models, Vol. 89 (Ed.: P. J. Sadler), Springer, Berlin, 1997, pp. 1-28;
30. d) E. Kimura, T. Koike, Comprehensive Supramolecular Chemistry, Vol. 10 (Ed.: D. N. Reinhoudt), Pergamon, Tokyo, 1996, pp. 429-444.
31. a) E. Kimura, T. Shiota, T. Koike, M. Shiro, M. Kodama, J. Am. Chem. Soc. 1990, 112, 5805-5811;
32. b) T. Koike, E. Kimura, J. Am. Chem. Soc. 1991, 113, 8935-8941;
33. c) T. Koike, E. Kimura, I. Nakamura, Y. Hashimoto, M. Shiro, J. Am. Chem. Soc. 1992, 114, 7338-7345;
34. d) E. Kimura, M. Shionoya, A. Hoshino, T. Ikeda, Y. Yamada, J. Am. Chem. Soc. 1992, 114, 10134-10137;
35. e) E. Kimura, I. Nakamura, T. Koike, M. Shionoya, Y. Kodama, T. Ikeda, M. Shiro, J. Am. Chem. Soc. 1994, 116, 4764-4771;
36. f) T. Koike, S. Kajitani, I. Nakamura, E. Kimura, M. Shiro, J. Am. Chem. Soc. 1995, 117, 1210-1219;
37. g) E. Kimura, Y. Kodama, T. Koike, M. Shiro, J. Am. Chem. Soc. 1995, 117, 8304-8311;
38. h) T. Koike, M. Inoue, E. Kimura, M. Shiro, J. Am. Chem. Soc. 1996, 118, 3091-3099;
39. i) T. Koike, H. Hashimoto, E. Kimura, J. Am. Chem. Soc. 1996, 118, 10963-10970.
40. T. Koike, M. Takamura, E. Kimura, J. Am. Chem. Soc. 1994, 116, 8443-8449.
41. E. Kimura, M. Shionoya, Metal Ions in Biological Systems, Vol. 33 (Eds.: A. Sigel, H. Sigel), Marcel Dekker, New York, 1996, pp. 29-52.
42. M. Shionoya, E. Kimura, M. Shiro, J. Am. Chem. Soc. 1993, 115, 6730-6737.
43. M. Shionoya, T. Ikeda, E. Kimura, M. Shiro, J. Am. Chem. Soc. 1994, 116, 3848-3859.
44. J. H. R. Tucher, M. Shionoya, T. Koike, E. Kimura, Bull. Chem. Soc. Jpn. 1995, 68, 2465-2469.
45. T. Koike, T. Gotoh, S. Aoki, E. Kimura, M. Shiro, Inorg. Chim. Acta 1998, 270, 424-432.
46. E. Kimura, T. Ikeda, M. Shionoya, Pure Appl. Chem. 1997, 69, 2187-2195.
47. M. Shionoya, M. Sugiyama, E. Kimura, J. Chem. Soc. Chem. Commun. 1994, 1747-1748.
48. E. Kimura, T. Ikeda, S. Aoki, M. Shionoya, J. Biol. Inorg. Chem. 1998, 3, 259-267.
49. T. Koike, M. Takashige, E. Kimura, H. Fujioka, M. Shiro, Chem. Eur. J. 1996, 2, 617-623.
50. E. Kimura, S. Aoki, T. Koike, M. Shiro, J. Am. Chem. Soc. 1997, 119, 3068-3076.
51. A. Dumont, V. Jacques, J. F. Desreux, Tetrahedron Lett. 1994, 35, 3707-3710.
52. A. E. Martell, R. J. Motekaitis, Determination and Use of Stability Constants, 2nd ed., VCH, New York, 1992.
53. H. Fujioka, T. Koike, N. Yamada, E. Kimura, Heterocycles 1996, 42, 775-787.
54. E. Freire, O. Mayorga, M. Straume, Anal. Chem. 1990, 62, 950-959.
55. a) T. Murata, T. Iwai, E. Ohtsuka, Nucleic Acids Res. 1990, 18, 7179-7286;
56. b) N. D. Sinha, J. Biernat, J. McManus, H. Köster, Nucleic Acids Res. 1984, 12, 4539-4558;
57. c) Methods in Molecular Biology, Protocols for Oligonucleotide Conjugates, Vol. 29 (Ed.: S. Agrawal), Humana Press, Towata, 1994.
58. II-cyclen) 9 was recently used to block photodimerization of TpT: S. Aoki, C. Sugimura, E. Kimura, J. Am. Chem. Soc. 1998, 120, 10094-10102.