Electron injection into DNA: Synthesis and spectroscopic properties of pyrenyl-modified oligonucleotides

Chemistry - A European Journal

Volumn 8, Issue 21, 2002, Pages 4877-4883

  Amann, Nicole ^a   Pandurski, Evgeni ^a   Fiebig, Torsten ^a   Wagenknecht, Hans Achim ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Charge transfer; DNA structures; Electron transfer; Pyrenes

Indexed keywords

FLUORESCENCE; SPECTROSCOPY; SYNTHESIS (CHEMICAL);

ELECTRON TRANSFER;

DNA;

5 (1 PYRENYL) 2' DEOXYURIDINE; DNA; DOUBLE STRANDED DNA; NUCLEIC ACID BASE; NUCLEOSIDE; OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; PYRENE; THYMINE; UNCLASSIFIED DRUG; URACIL; FLUORESCENT DYE; PYRENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COVALENT BOND; DNA MODIFICATION; DNA SEQUENCE; ELECTRON; ELECTRON TRANSPORT; EXCITATION; FLUORESCENCE; INJECTION; SPECTROSCOPY; SYNTHESIS; CHEMISTRY; SPECTROFLUOROMETRY;

DNA; ELECTRONS; FLUORESCENT DYES; OLIGONUCLEOTIDES; PYRENES; SPECTROMETRY, FLUORESCENCE; THYMINE;

EID: 2242492680     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021104)8:21<4877::AID-CHEM4877>3.0.CO;2-P     Document Type: Article

References (69)

1. a) M. R. Arkin, E. D. A. Stemp, R. E. Holmlin, J. K. Barton, A. Hörmann, E. J. C. Olson, P. F. Barbara, Science 1996, 273, 475;
2. b) K. Fukui, K. Tanaka, Angew. Chem. 1998, 110, 167; Angew. Chem. Int. Ed. 1998, 37, 158;
3. b) K. Fukui, K. Tanaka, Angew. Chem. 1998, 110, 167; Angew. Chem. Int. Ed. 1998, 37, 158;
4. c) S. O. Kelley, J. K. Barton, Science 1999, 283, 375;
5. d) J. M. Jean, J. M., K. B. Hall, Proc. Natl. Acad. Sci. USA 2001, 98, 37;
6. e) M. Kawai, M. J. Lee, K. O. Evans, T. M. Nordlund, J. Fluoresc. 2001, 11, 23;
7. f) O. F. A. Larsen, I. H. M. van Stokkum, B. Gobets, R. van Grondelle, H. van Amerongen, Biophys. J. 2001, 81, 1115.
8. a) E. D. A. Stemp, M. R. Arkin, J. K. Barton, J. Am. Chem. Soc. 1997, 119, 2921;
9. b) F. D. Lewis, X. Liu, J. Liu, S. E. Miller, R. T. Hayes, M. R. Wasielewski, Nature 2000, 406, 51;
10. c) C. Wan, T. Fiebig, O. Schiemann, J. K. Barton, A. H. Zewail, Proc. Natl. Acad. Sci. USA 2000, 97, 14052;
11. d) V. Shafirovich, A. Dourandin, W. Huang, N. P. Luneva, N. E. Geacintov, J. Phys. Chem. B 1999, 103, 10924;
12. e) H.-A. Wagenknecht, S. R. Rajski, M. Pascaly, E. D. A. Stemp, J. K. Barton, J. Am. Chem. Soc. 2001, 123, 4400;
13. f) W. B. Davies, S. Hess, I. Naydenova, R. Haselsberger, A. Ogrodnik, M. D. Newton, M. E. Michel-Beyerle, J. Am. Chem. Soc. 2002, 124, 2422;
14. g) F. D. Lewis, Y. Wu, J. Photochem. Photobiol. C 2001, 2, 1.
15. O. Schiemann, N. J. Turro, J. K. Barton, J. Phys. Chem. B 2000, 104, 7214.
16. a) M. E. Nunez, J. K. Barton, Curr. Opin. Chem. Biol. 2000, 4, 199;
17. b) G. B. Schuster, Acc. Chem. Res. 2000, 33, 253;
18. c) T. T. Williams, J. K. Barton, J. Am. Chem. Soc. 2002, 124, 1840;
19. d) K. Nakatani, C. Dohno, A. Ogawa, I. Saito, Chem. Biol. 2002, 9, 361;
20. e) B. Giese, A. Biland, Chem. Commun. 2002, 667.
21. a) P. O'Neill, M. Fielden, Adv. Radiat. Biol. 1993, 17, 53;
22. b) D. Wang, D. A. Kreutzer, J. M. Essigmann, Mutat. Res. 1998, 400, 99.
23. a) N. M. Jackson, M. G. Hill, Curr. Opin. Chem. Biol. 2001, 5, 209;
24. b) E. M. Boon, J. E. Salas, J. K. Barton, Nat. Biotechnol. 2002, 20, 282;
25. c) M. C. Pirrung, Angew. Chem. 2002, 114, 1326; Angew. Chem. Int. Ed. 2002, 41, 1276.
26. c) M. C. Pirrung, Angew. Chem. 2002, 114, 1326; Angew. Chem. Int. Ed. 2002, 41, 1276.
27. a) C. Mao, W. Sun, Z. Shen, N. C. Seeman, Nature 1999, 397, 144;
28. b) H.-W. Fink, C. Schönenberger, Nature 1999, 398, 407;
29. c) D. Porath, A. Bezryadin, S. de Vries, C. Dekker, Nature 2000, 403, 635;
30. d) C. M. Niemeyer, Angew. Chem. 2001, 113, 4254; Angew. Int. Ed. 2001, 40, 4128.
31. d) C. M. Niemeyer, Angew. Chem. 2001, 113, 4254; Angew. Int. Ed. 2001, 40, 4128.
32. R. E. Holmlin, P. J. Dandliker, J. K. Barton, Angew. Chem. 1997, 109, 2830; Angew. Chem. Int. Ed. 1997, 36, 2714.
33. R. E. Holmlin, P. J. Dandliker, J. K. Barton, Angew. Chem. 1997, 109, 2830; Angew. Chem. Int. Ed. 1997, 36, 2714.
34. E. J. C. Olson, D. Hu, A. Hörmann, A. M. Jonkman, M. R. Arkin, E. D. A. Stemp, J. K. Barton, P. F. Barbara, J. Am. Chem. Soc. 1997, 119, 11458.
35. a) A. Schwögler, L. T. Burgdorf, T. Carell, Angew. Chem. 2000, 112, 4082; Angew. Chem. Int. Ed. 2000, 39, 3918;
36. a) A. Schwögler, L. T. Burgdorf, T. Carell, Angew. Chem. 2000, 112, 4082; Angew. Chem. Int. Ed. 2000, 39, 3918;
37. b) C. Behrens, L. T. Burgdorf, A. Schwögler, T. Carell, Angew. Chem. 2002, 114, 1841; Angew. Chem. Int. Ed. 2002, 41, 1763.
38. b) C. Behrens, L. T. Burgdorf, A. Schwögler, T. Carell, Angew. Chem. 2002, 114, 1841; Angew. Chem. Int. Ed. 2002, 41, 1763.
39. T. Carell, L. T. Burgdorf, L. M. Kundu, M. Cichon, Curr. Opin. Chem. Biol. 2001, 5, 4911.
40. a) B. Giese, M. Spichty, ChemPhysChem 2000, 1, 195;
41. b) B. Giese, J. Amaudrut, A.-K. Köhler, M. Spormann, S. Wessely, Nature 2001, 412, 318.
42. T. Fiebig, C. Wan, A. H. Zewail, ChemPhysChem 2002, 3, in press.
43. E. T. Kool, J. C. Morales, K. M. Guckian, Angew. Chem. 2000, 112, 1046; Angew. Chem. Int. Ed. 2000, 39, 990.
44. E. T. Kool, J. C. Morales, K. M. Guckian, Angew. Chem. 2000, 112, 1046; Angew. Chem. Int. Ed. 2000, 39, 990.
45. a) V. A. Korshun, N. B. Pestov, K. R. Birikh, Y. A. Berlin, Bioconjugate Chem. 1992, 3, 559;
46. b) I. A. Prokhorenko, V. A. Korshun, A. A. Petrov, S. V. Gontarev, Y. A. Berlin, Bioorg. Med. Chem. Lett. 1995, 5, 2081;
47. c) K. V. Balakin, V. A. Korshun, I. I. Mikhalev, G. V. Maleev, A. D. Malakhov, I. A. Prokhorenko, Y. A. Berlin, Biosens. Bioelectron. 1998, 13, 771.
48. a) R. Kierzek, Y. Li, D. H. Turner, P. C. Bevilacqua, J. Am. Chem. Soc. 1993, 115, 4985;
49. b) M. Manoharan, K. L. Tivel, M. Zhao, K. Nafisi, T. L. Netzel, J. Phys. Chem. 1995, 99, 17461;
50. c) F. D. Lewis, Y. Zhang, R. L. Letsinger, J. Am. Chem. Soc. 1997, 119, 5451;
51. d) K. Yamana, M. Takei, H. Nakano, Tetrahedron Lett. 1997. 38, 6051;
52. e) J. D. Frazer, S. M. Horner, S. A. Woski, Tetrahedron Lett. 1998, 39, 1279.
53. T. L. Netzel, M. Zhao, K. Nafisi, J. Headrick, M. S. Sigman, B. E. Eaton, J. Am. Chem. Soc. 1995, 117, 9119.
54. V. Y. Shafirovich, S. H. Courtney, N. Ya, N. E. Geacintov, J. Am. Chem. Soc. 1995, 117, 4920.
55. T. L. Netzel, K. Nafisi, J. Headrick, B. E. Eaton, J. Phys. Chem. 1995, 99, 17948.
56. T. Kubota, J. Kano, B. Uno, T. Konse, Bull. Chem. Soc. Jpn. 1987, 60, 3865.
57. S. Steenken, J. P. Telo, H. M. Novais, L. P. Candeias, J. Am. Chem. Soc. 1992, 114, 4701.
58. C. A. M. Seidel, A. Schulz, M. H. M. Sauer, J. Phys. Chem. 1996, 100, 5541.
59. E. Pandurski, N. Amann, H.-A. Wagenknecht, T. Fiebig, unpublished results.
60. N. Amann, E. Pandurski, T. Fiebig, H.-A. Wagenknecht, Angew. Chem. 2002, 114, 3084; Angew Chem. Int. Ed. 2002, 41, 2978.
61. N. Amann, E. Pandurski, T. Fiebig, H.-A. Wagenknecht, Angew. Chem. 2002, 114, 3084; Angew Chem. Int. Ed. 2002, 41, 2978.
62. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
63. N. Amann, H.-A. Wagenknecht, Synlett 2002, 687.
64. a) M. Havelková, D. Dvořák, M. Hocek, Synthesis 2001, 1704-1710;
65. b) M. Hocek, A. Holý, H. Dvořáková, Collect. Czech. Chem. Commun. 2002, 67, 325-335.
66. a) H. Suenaga, K. Nakashima, T. Mizuno, M. Takeuchi, I. Hamachi, S. Shinkai, J. Chem. Soc. Perkin Trans. 1 1998, 1263;
67. b) M. Beinhoff, W. Weigel, M. Jurczok, W. Rettig, C. Modrakowski, I. Brüdgam, H. Hartl, A. D. Schlüter, Eur. J. Org. Chem. 2001, 3819.
68. P. Foggi, L. Pettini, I. Sánta, R. Righini, S. Califano, J. Phys. Chem. 1995, 99, 7439.
69. J. D. Puglisi, I. Tinoco, Meth. Enzymol. 1989, 180, 304.