A doorway state leads to photostability or triplet photodamage in thymine DNA

Journal of the American Chemical Society

Volumn 130, Issue 15, 2008, Pages 5131-5139

  Kwok, Wai Ming ^a   Ma, Chensheng ^b   Phillips, David Lee ^b  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; DIMERS; EXCITED STATES; OLIGONUCLEOTIDES; ULTRASHORT PULSES;

PHOTOSTABILITY; THYMINES;

DNA;

CYCLOBUTANE; DIMER; MONOMER; OLIGONUCLEOTIDE; PYRIMIDINE; THYMINE;

ABSORPTION SPECTROSCOPY; ARTICLE; DIMERIZATION; DNA DAMAGE; ENERGY; FLUORESCENCE; MOLECULAR DYNAMICS; MOLECULAR STABILITY; MUTAGENESIS; PHOTOCHEMISTRY; ULTRAVIOLET IRRADIATION;

DNA; DNA DAMAGE; PHOTOCHEMISTRY; PYRIMIDINE DIMERS; SPECTRUM ANALYSIS; THYMINE; TIME FACTORS;

EID: 42149150942     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077831q     Document Type: Article

References (111)

1. Cadet, J.; Vigny, P. In The Photochemistry of Nucleic Acids; Morrison, H., Ed.; Wiley: New York, 1990; pp 1-272.
2. (a) Borgdorff, V.; Pauw, B.; Hees-Stuivenberg, S.; Wind, N. DNA Repair 2006, 5, 1364-1372.
3. (b) Ikehata, H.; Ono, T.; Tanaka, K.; Todo, T. DNA Repair 2007, 6, 658-668.
4. (c) Nijhof, J. G. W.; Mulder, A. M.; Speksnijder, E. N.; Hoogervorst, E. M.; Mullenders, L. H. F.; Gruijl, F. R. DNA Repair 2007, 6, 1642-1650.
5. (d) Queille, S.; Luron, L.; Spatz, A.; Avril, M. F.; Ribrag, V.; Duvillard, P.; Hiesse, C.; Sarasin, A.; Armand, J. P.; Daya-Grosjean, L. Carcinogenesis 2007, 28, 724-731.
6. (a) Douki, T.; Court, M.; Sauvaigo, S.; Odin, F.; Cadet, J. J. Biol. Chem. 2000, 275, 11678-11685.
7. (b) Douki, T.; Angelov, D.; Cadet, J. J. Am. Chem. Soc. 2001, 123, 11360-11366.
8. (c) Douki, T.; Reynaud-Angelin, A.; Cadet, J.; Sage, E. Biochemistry 2003, 42, 9221-9226.
9. (d) Douki, T. J. Photochem. Photobiol. B: Biol. 2006, 83, 45-52.
10. (e) Cadet, J.; Courdavault, S.; Ravanat, J. L.; Douki, T. Pure Appl. Chem. 2005, 77, 947-961.
11. Becker, M. M.; Wang, Z. J. Mol. Biol. 1989, 210, 429-438.
12. (a) Beukers, R.; Berends, W. Biochim. Biophys. Acta 1960, 41, 550-551.
13. (b) Beukers, R.; Ijlstra, J.; Berends, W. Rec. Trav. Chim. 1960, 79, 101-104.
14. (a) Wulff, D. L.; Fraenkel, G. Biochim. Biophys. Acta 1961, 51, 332-339.
15. (b) Johns, H. E.; Pearson, M. L.; LeBlanc, J. C.; Helleiner, C. W. J. Mol. Biol. 1964, 9, 503-524.
16. (a) Pecourt, J. L.; Peon, J.; Kohler, B. J. Am. Chem. Soc. 2001, 123, 10370-10378.
17. (b) Pecourt, J. L.; Peon, J.; Kohler, B. J. Am. Chem. Soc. 2000, 122, 9348-9349.
18. Crespo-Hernández, C. E.; Cohen, B.; Hare, P. M.; Kohler, B. Chem. Rev. 2004, 104, 1977-2019.
19. Marguet, S.; Markovitsi, D. J. Am. Chem. Soc. 2005, 127, 5780-5781.
20. Salet, C.; Bensasson, R.; Becker, R. S. Photochem. Photobiol. 1979, 30, 325-329.
21. Lamola, A. A.; Yamane, T. Proc. Natl. Acad. Sci. U.S.A. 1967, 58, 443-446.
22. Lamola, A. A.; Mittal, J. P. Science 1966, 154, 1560-1561.
23. Moysan, A.; Viari, A.; Vigny, P.; Voituriez, L.; Cadet, J.; Moustacchi, E.; Sage, E. Biochemistry 1991, 30, 7080-7088.
24. Schreier, W. J.; Schrader, T. E.; Koller, F. O.; Gilch, P.; Crespo-Hernández, C. E.; Swaminathan, V. N.; Carell, T.; Zinth, W.; Kohler, B. Science 2007, 315, 625-629.
25. Nikogosyan, D. N. Int. J. Radiat. Biol. 1990, 57, 233-299.
26. (a) Görner, H. J. Photochem. Photobiol. B: Biol. 1994, 26, 117-139.
27. (b) Görner, H. Photochem. Photobiol. 1990, 52, 935-948.
28. Eisinger, J.; Shulman, R. G. Science 1968, 161, 1311-1319.
29. Kwok, W.-M.; Ma, C.; Phillips, D. L. J. Am. Chem. Soc. 2006, 128, 11894-11905.
30. Crespo-Hernández, C. E.; Cohen, B.; Kohler, B. Nature 2005, 436, 1141-1144.
31. (a) Markovitsi, D.; Talbot, F.; Gustavsson, T.; Onidas, D.; Lazzarotto, E.; Marguet, S. Nature 2006, 441 (7094), E7-E7.
32. (b) Markovitsi, D.; Onidas, D.; Gustavsson, T.; Talbot, F.; Lazzarotto, E. J. Am. Chem. Soc. 2005, 127, 17130-17131.
33. (c) Markovitsi, D.; Gustavsson, T.; Talbot, F. Photochem. Photobiol. Sci. 2007, 7, 717-724.
34. Plessow, R.; Brockhinke, A.; Eimer, W.; Kohse-Höinghaus, K. J. Phys. Chem. B 2000, 104, 3695-3704.
35. (a) Buchvarov, I.; Wang, Q.; Raytchev, M.; Trifonov, A.; Fiebig, T. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 4794-4797.
36. (b) Wang, Q.; Raytchev, M.; Fiebig, T. Photochem. Photobiol. 2007, 83, 637-641.
37. Santoro, F.; Barone, V.; Improta, R. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 9931-9936.
38. Crespo-Hernández, C. E.; Kohler, B. J. Phys. Chem. B 2004, 108, 11182-11188.
39. (a) Boggio-Pasqua, M.; Groenhof, G.; Schäfer, L. V.; Grubmüller, H.; Robb, M. A. J. Am. Chem. Soc. 2007, 129, 10996-10997.
40. (b) Blancafort, L.; Migani, A. J. Am. Chem. Soc. 2007, 129, 14540-14541.
41. (a) Zhang, R. B.; Eriksson, L. A. J. Phys. Chem. B 2006, 110, 7556-7562.
42. (b) Durbeej, B.; Eriksson, L. A. J. Photochem. Photobiol., A 2002, 151, 95-101.
43. Ma, C.; Kwok, W. M.; Chan, W. S.; Zuo, P.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. J. Am. Chem. Soc. 2005, 127, 1463-1427.
44. Ma, C.; Kwok, W. M.; Chan, W. S.; Du, Y.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. J. Am. Chem. Soc. 2006, 128, 2558-2570.
45. Matousek, P.; Towrie, M.; Ma, C.; Kwok, W-M.; Phillips, D.; Toner, W. T.; Parker, A. W. J. Raman Spectrosc. 2001, 32, 983-988.
46. Matousek, P.; Towrie, M.; Stanley, A.; Parker, A. W. Appl. Spectrosc. 1999, 53, 1485-1489.
47. Lorenton, J.; Fülscher, M. P.; Roos, B. O. J. Am. Chem. Soc. 1995, 117, 9265-9273.
48. Broo, A.; Holmén, A. J. Phys. Chem. A 1997, 101, 3589-3600.
49. Gustavsson, G.; Bányász, Á.; Lazzarotto, E.; Markovitsi, D.; Scalmani, G.; Frisch, M. J.; Barone, V.; Improta, R. J. Am. Chem. Soc. 2006, 128, 607-619.
50. Perun, S.; Sobolewski, A. L.; Domcke, W. J. Phys. Chem. A 2006, 110, 13238-13244.
51. Morsy, M. A.; Al-Somali, A. M.; Suwaiyan, A. J. Phys. Chem. B 1999, 103, 11205-11210.
52. Suwaiyan, A.; Morsy, M. A.; Odah, K. A. Chem. Phys. Lett. 1995, 237, 349-355.
53. Markova, N.; Enchev, V.; Timtcheva, I. J. Phys. Chem. A 2005, 109, 1981-1988.
54. Hanus, M.; Kabeláč, M.; Nachtigallová, A.; Hobza, P. Biochemistry 2005, 44, 1701-1707.
55. (a) Onidas, D.; Markovitsi, D.; Marguet, S.; Sharonov, A.; Gustavsson, T. J. Phys. Chem. B 2002, 106, 11367-11374.
56. (b) Gustavsson, T.; Sharonov, A.; Markovitsi, D. Chem. Phys. Lett. 2002, 351, 195-200.
57. Markovitsi, D.; Sharonov, A.; Onidas, D.; Gustavsson, T. ChemPhysChem 2003, 3, 303-305.
58. Peon, J.; Zewail, A. H. Chem. Phys. Lett. 2001, 348, 255-262.
59. Gut, I. G.; Wood, P. D.; Redmond, R. W. J. Am. Chem. Soc. 1996, 118, 2366-2373.
60. Callis, P. R. Annu. Rev. Phys. Chem. 1983, 34, 329-357.
61. (a) Hare, P. M.; Crespo-Hernández, C. E.; Kohler, B. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 435-440.
62. (b) Hare, P. M.; Crespo-Hernández, C. E.; Kohler, B. J. Phys. Chem. B 2006, 110, 18641-18650.
63. Shulman, R. G.; Rahn, R. O. J. Chem. Phys. 1966, 45, 2940-2946.
64. (a) Tinoco, I. J. Am. Chem. Soc. 1960, 83, 4765-4789.
65. (b) Rhoders, W. J. Am. Chem. Soc. 1961, 83, 3609-3617.
66. Lamola, A. A.; Guéron, M.; Yamane, T.; Eisinger, J.; Shulman, R. G. J. Chem. Phys. 1967, 47, 2210-2217.
67. Whillans, D. W.; Johns, H. E. J. Am. Chem. Soc. 1971, 93, 1358-1362.
68. Wagner, P. J.; Bucheck, D. J. J. Am. Chem. Soc. 1970, 92, 181-185.
69. Wagner, P. J.; Bucheck, D. J. J. Am. Chem. Soc. 1969, 91, 5090-5097.
70. (a) Sobolewski, A. L.; Domcke, W.; Hattig, C. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 17903-17906.
71. (b) Schultz, T.; Samoylova, E.; Radloff, W.; Hertel, I. V.; Sobolewski, A. L.; Domcke, W. Science 2004, 306, 1765-1768.
72. (c) Schwalb, N. K.; Temps, F. J. Am. Chem. Soc. 2007, 129, 9272-9273.
73. (a) Camerman, N.; Fawcett, J. K.; Camerman, A. J. Mol. Biol. 1976, 107, 601-621.
74. (b) Martinez, J. M.; Elmroth, S. K. C.; Kloo, L. J. Am. Chem. Soc. 2001, 123, 12279-12289.
75. (c) Mills, J. B.; Vacano, E.; Hagerman, P. L. J. Mol. Biol. 1999, 285, 245-257.
76. Turro, N. J. Modern Molecular Photochemistry; University Science Book: Mill Valley, CA, 1991.
77. (a) Merchán, M.; Serrano-Andrés, L.; Robb, M. A.; Blancafirt, L. J. Am. Chem. Soc. 2005, 127, 1820-1825.
78. (b) Blancafirt, L.; Robb, M. A. J. Phys. Chem. A 2004, 108, 10609-10614.
79. Improta, R.; Barone, V. J. Am. Chem. Soc. 2004, 126, 14320-14321.
80. (a) Matsika, S. J. Phys. Chem. A 2004, 108, 7584-7590.
81. (b) Matsika, S. J. Phys. Chem. A 2005, 109, 7538-7545.
82. (a) Marian, C. M.; Schneider, F.; Kleinschmidt, M.; Tatchen, J. Eur. Phys. J. 2002, D20, 357-367.
83. (b) Marian, C. M. J. Chem. Phys. 2005, 122, 104314.
84. Ismail, N.; Blancafirt, L.; Olivucci, M.; Kohler, B.; Robb, M. A. J. Am. Chem. Soc. 2002, 124, 6818-6819.
85. Merchán, M.; Serrano-Andrés, L. J. Am. Chem. Soc. 2003, 125, 8108-8109.
86. Cohen, B.; Crespo-Hernández, C. E.; Kohler, B. Faraday Discuss. 2004, 127, 137-147.
87. (a) Lim, E. C. J. Phys. Chem. 1986, 90, 6770-6777.
88. (b) Lai, T.-i.; Lim, E. C. Chem. Phys. Lett. 1980, 73, 244-248.
89. Broo, A. J. Phys. Chem. A 1998, 102, 526-531.
90. Mennucci, B.; Toniolo, A.; Tomasi, J. J. Phys. Chem. A 2001, 105, 7126-7134.
91. Dym, S.; Hochstrasser, R. M. J. Chem. Phys. 1969, 51, 2458-2468.
92. (a) Kearns, D. R.; Case, W. A. J. Am. Chem. Soc. 1966, 88, 5087-5097.
93. (b) Case, W. A.; Kearns, D. R. J. Chem. Phys. 1970, 52, 2175-2191.
94. Kang, H.; Lee, K. T.; Jung, B.; Ko, Y. J.; Kim, S. K. J. Am. Chem. Soc. 2002, 124, 12958-12959.
95. Samoylova, E.; Lippert, H.; Ullrich, S.; Hertel, I. V.; Radloff, W.; Schultz, T. J. Am. Chem. Soc. 2005, 127, 1782-1786.
96. Canuel, C.; Mons, M.; Piuzzi, F.; Iardivel, B.; Dimicoli, I.; Elhanine, M. J. Chem. Phys. 2005, 122, 074316.
97. (a) He, Y.; Wu, C.; Kong, W. J. Phys. Chem. A 2004, 108, 943-949.
98. (b) He, Y.; Wu, C.; Kong, W. J. Phys. Chem. A 2003, 107, 5145-5148.
99. Brady, B. B.; Peteanu, L. A.; Levy, D. H. Chem. Phys. Lett. 1988, 147, 538-543.
100. Scaiano, J. C. J. Am. Chem. Soc. 1980, 102, 7747-7753.
101. Dalton, J. C.; Montgomery, F. C. J. Am. Chem. Soc. 1974, 96, 6230-6232.
102. Rusakowicz, R.; Byers, G. W.; Leermakers, P. A. J. Am. Chem. Soc. 1971, 93, 3263-3266.
103. Reichardt, C. Solvent and Solvent Effects in Organic Chemistry; VCH: Weinheim, Germany, 1988.
104. (a) Santoro, F.; Barone, V.; Gustavsson, T.; Improta, R. J. Am. Chem. Soc. 2006, 128, 16312-16322.
105. (b) Gustavsson, T.; Sarkar, N.; Lazzarotto, E.; Markovitsi, D.; Barone, V.; Improta, R. J. Phys. Chem. B 2006, 110, 12843-12847.
106. (c) Gustavsson, T.; Sarkar, N.; Lazzarotto, E.; Markovitsi, D.; Improta, R. Chem. Phys. Lett. 2006, 429, 551-557.
107. Häupl, T.; Wiindolph, C.; Jochum, T.; Brede, O.; Hermann, R. Chem. Phys. Lett. 1997, 280, 520-524.
108. (a) Shishkin, O. V.; Gorb, L.; Leszczynski, J. Int. J. Mol. Sci. 2000, 1, 17-27.
109. (b) Shishkin, O. V.; Hobza, P.; Leszczynski, J. Int. J. Quantum Chem. 2000, 80, 1116-1124.
110. Salet, C.; Bensasson, R. Photochem. Photobiol. 1975, 22, 231-235.
111. Becker, R.; Kogan, G. Photochem. Photobiol. 1980, 31, 5-13.