DNA cleavage via superoxide anion formed in photoinduced electron transfer from NADH to γ-cyclodextrin-bicapped C60 in an oxygen-saturated aqueous solution

Journal of Physical Chemistry B

Volumn 106, Issue 9, 2002, Pages 2372-2380

  Nakanishi, Ikuo ^a,b   Fukuzumi, Shunichi ^c   Konishi, Toshifumi ^d   Ohkubo, Kei ^c   Fujitsuka, Mamoru ^d   Ito, Osamu ^d   Miyata, Naoki ^b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^c OSAKA UNIVERSITY   (Japan)

^d TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON TRANSFER;

FULLERENES; HYDROGEN PEROXIDE; IRRADIATION; NEGATIVE IONS; OXYGEN; PARAMAGNETIC RESONANCE; PHOTOSENSITIZERS; REDUCTION;

DNA;

EID: 0037035210     PISSN: 10895647     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp013215j     Document Type: Article

References (93)

1. (a) Arbogast, J.W.; Darmanyan, A.P.; Foote, C.S.; Rubin, Y.; Diedrich, F.N.; Alverez, M.M.; Anz, S.J.; Whetten, R.L. J. Phys. Chem. 1991, 95, 11.
2. (b) Arbogast, J.W.; Foote, C.S. J. Am. Chem. Soc. 1991, 113, 8886.
3. Nagano, T.; Arakane, K.; Ryu, A.; Masunaga, T.; Shinmoto, K.; Mashiko, S.; Hirobe, M. Chem. Pharm. Bull. 1994, 42, 2291.
4. Wilson, S.R. In Fullerenes: Chenistry, Physics, and Technology; Kadish, K.M., Ruoff, R.S., Eds.; Wiley: New York, 2000; pp 437-465.
5. (a) Jensen, A.W.; Wilson, S.R.; Schuster, D.I. Bioorganic Med. Chem. 1996, 4, 767.
6. (b) Da Ros, T.; Prato, M. Chem. Commun. 1999, 663.
7. (c) Xu, Z.; Suo, Z.Y.; Wei, X.W.; Zhu, D.X. Prog. Biochim. Biophys. 1998, 25, 130.
8. Wan, S.; Parrish, J.A.; Anderson, R.R.; Madden, M. Photochem. Photobiol. 1981, 34, 679.
9. (a) Tsuchiya, T.; Yamakoshi, Y.N.; Miyata, N. Biochem. Biophys. Res. Commun. 1995, 206, 885.
10. (b) Tsuchiya, T.; Oguri, I.; Yamakoshi, Y.N.; Miyata, N. Fullerene Sci. Technol. 1996, 4, 989.
11. HIV-1 protease inhibition: (a) Friedman, S.H.; DeCamp, D.L.; Sijbesma, R.P.; Srdanov, G.; Wudl, F.; Kenyon, G.L. J. Am. Chem. Soc. 1993, 115, 6505.
12. (b) Toniolo, C.; Bianco, A.; Maggini, M.; Scorrano, G.; Prato, M.; Marastoni, M.; Tomatis, R.; Spisani, S.; Palú, R.; Blair, E.D. J. Med. Chem. 1994, 37, 4558.
13. Glutathione S-transferase inhibition: (c) Iwata, N.; Mukai, T.; Yamakoshi, Y.; Hara, S.; Yanase, T.; Shoji, M.; Endo, T.; Miyata, N. Fullerene Sci. Technol. 1998, 6, 213.
14. (a) Chiang, L.Y.; Lu, F.-J.; Lin, J.-T. J. Chem. Soc., Chem. Commun. 1995, 1283.
15. (b) Lai, Y.-L.; Chiou, W.-Y.; Chiang, L.Y. Fullerene Sci. Technol. 1997, 5, 1057.
16. (a) Tokuyama, H.; Yamago, S.; Nakamura, E.; Shiraki, T.; Sugiura, Y. J. Am. Chem. Soc. 1993, 115, 7918.
17. (b) Boutorine, A.S.; Tokuyama, H.; Takasugi, M.; Isobe, H.; Nakamura, E.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 2462.
18. (c) Irie, K.; Nakamura, Y.; Ohigashi, H.; Tokuyama, H.; Yamago, S.; Nakamura, E. Biosci. Biotechnol, Biochem. 1996, 60, 1359.
19. (d) Nakamura, E.; Tokuyama, H.; Yamago, S.; Shiraki, T.; Sugiura, Y. Bull. Chem. Soc. Jpn. 1996, 69, 2143.
20. An, Y.-Z.; Chen, C.-H.B.; Anderson, J.L.; Sigman, D.S.; Foote C.S.; Rubin, T. Tetrahedron 1996, 52, 5179.
21. (a) Yamakoshi, Y.; Sueyoshi, S.; Fukuhara, K.; Miyata, N.; Masumizu, T.; Kohno, M. J. Am. Chem. Soc. 1998, 120, 12363.
22. (b) Yamakoshi, Y.; Yagami, T.; Sueyoshi, S.; Miyata, N. J. Org. Chem. 1996, 61, 7236.
23. (c) Sera, N.; Tokiwa, H.; Miyata, N. Carcinogenesis 1996, 17, 2163.
24. Foote, C.S. Top. Curr. Chem. 1994, 169, 347.
25. Arbogast, J.W.; Foote, C.S.; Kao, M. J. Am. Chem. Soc. 1992, 114, 2277.
26. Fukuzumi, S.; Guldi, D.M. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 270-337.
27. (a) Fujitsuka, M.; Luo, C.; Ito, O. J. Phys. Chem. B 1999, 103, 445.
28. (b) Luo, C.; Fujitsuka, M.; Huang, C.-H.; Ito, O. J. Phys. Chem. A 1998, 102, 8716.
29. (c) Luo, C.; Fujitsuka, M.; Huang, C.-H.; Ito, O. Phys. Chem. Chem. Phys. 1999, 1, 2923.
30. (d) Rath, M.C.; Pal, H.; Mukherjee, T. J. Phys. Chem. A 1999, 103, 4993.
31. Guldi, D.M.; Kamat, P.V. In Fullerenes: Chemistry, Physics, and Technology; Kadish, K.M., Ruoff, R.S., Eds.; Wiley: New York; 2000, pp 225-281.
32. (a) Ghosh, H.N.; Pal, H.; Sapre, A.; Mittal, J.P. J. Am. Chem. Soc. 1993, 115, 11722.
33. (b) Fukuzumi, S.; Suenobu, T.; Patz, M.; Hirasaka, T.; Itoh, S.; Fujitsuka, M.; Ito, O. J. Am. Chem. Soc. 1998, 120, 8060.
34. (c) Fukuzumi, S.; Suenobu, T.; Fujitsuka, M.; Ito, O.; Tonoi, T.; Matsumto, S.; Mikami, K. J. Organomet. Chem. 1999, 574, 32.
35. (d) Mikami, K.; Matsumoto, S.; Okubo, Y.; Fujitsuka, M.; Ito, O.; Suenobu, T.; Fukuzumi, S. J. Am. Chem. Soc. 2000, 122, 2236.
36. Reed, C.A.; Bolskar, R.D. Chem. Rev. 2000, 100, 1075.
37. Fukuzumi, S.; Mori, H.; Snenobu, T.; Imahori, H.; Gao, X.; Kadish, K.M. J. Phys. Chem. A 2000, 104, 10688.
38. Bernstein, R.; Prat, F.; Foote, C.S. J. Am. Chem. Soc. 1999, 121, 464.
39. Sheu, C.; Foote, C.S. J. Am. Chem. Soc. 1995, 117, 6439.
40. (a) Fujitsuka, M.; Ito, O.; Yamashiro, T.; Aso, Y.; Otsubo, T. J. Phys. Chem. A 2000, 104, 4876.
41. (b) Ito, O.; Yamazaki, M.; Fujitsuka, M. In Fullerenes 2000 Volume 8: Electrochemistry and Photochemistry; Fukuzumi, S., D'Souza, F., Guldi, D.M., Eds.; The Electrochemical Soceity: Pennington, 2000; pp 306-318.
42. (a) Andersson, T.; Nilsson, K.; Sundahl, M.; Westman, G.; Wennerström, O. J. Chem. Soc., Chem. Commun. 1992, 604.
43. (b) Kutner, W.; Boulas, P.; Kadish, K.M. J. Electrochem. Soc. 1992, 139, 243C.
44. (c) Sundahl, M.; Andersson, T.; Nilsson, K.; Wennerström, O.; Westman, G. Synth. Met. 1993, 55-57, 3252.
45. (d) Andersson, T.; Westman, G.; Wennerström, O.; Sundahl, M. J. Chem. Soc, Perkin Trans. 2 1994, 1097.
46. (e) Boulas, P.; Kutner, W.; Jones, M.T.; Kadish, K.M. J. Phys. Chem. 1994, 98, 1282.
47. (f) Priyadarsini, K.I.; Mohan, H.; Mittal, J.P. Fullerene Sci. Technol. 1995, 3, 479.
48. (g) Yoshida, Z.; Takekuma, H.; Takekuma, S.; Matsubara, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 1597.
49. (h) Buvari-Barcza, A.; Barcza, L.; Braun, T.; Supramol. Chem. 1994, 4, 131.
50. (i) Buvari-Barcza, A.; Barcza, L.; Braun, T.; Konkoly-Thege, I.; Ludanyi, K.; Vekey, K. Fullerene Sci. Technol. 1997, 5, 331.
51. (j) Braun, T. Fullerene Sci. Technol. 1997, 74, 47.
52. Ohlendorf, V.; Willnow, A.; Hungerbühler, H.; Guldi, D.M.; Asmus, K.-D. J. Chem. Soc., Chem. Commun. 1995, 759.
53. (a) Priyadarsini, K.I.; Mohan, H.; Mittal, J.P.; Guldi, D.M.; Hungerbühler, H.; Asmus, K.-D. J. Phys. Chem. 1994, 98, 9565.
54. (b) Priyadarsini, K.I.; Mohan, H.; Tyagi, A.K.; Mittal, J.P. J. Phys. Chem. 1994, 98, 4756.
55. Yamakoshi, Y.N.; Yagami, T.; Fukuhara, K.; Sueyoshi, S.; Miyata, N. J. Chem. Soc., Chem. Commun. 1994, 517.
56. (a) Frejaville, C.; Karoui, H.; Tuccio, B.; Lemoigne, F.; Culcasi, M.; Pietri, S.; Lauricella, R.; Tordo, P. J. Med. Chem. 1995, 38, 258.
57. (b) Karoui, H.; Hogg, N.; Fréjaville, C.; Tordo, P.; Kalyanaraman, B. J. Biol. Chem. 1996, 271, 6000.
58. (c) Vásquez-Vivar, J.; Hogg, N.; Pritchard, Jr., K.A.; Martasek, P.; Kalyanaraman, B. FEBS Lett. 1997, 404, 127.
59. (a) Komatsu, K.; Fujiwara, K.; Murata, Y.; Braun, T. J. Chem. Soc., Perkin Trans. 1 1999, 2963.
60. (b) Braun, T.; Buvari-Barcza, A.; Barcza, L.; Konkoly-Thege, I.; Fodor, M.; Migali, B. Solid State Ionics 1994, 74, 47.
61. Masuhara, A.; Fujitsuka, M.; Ito, O. Bull. Chem. Soc. Jpn. 2000, 73, 2199.
62. Watanabe, A.; Ito, O. J. Phys. Chem. 1994, 98, 7736.
63. Konishi, T.; Sasaki, Y.; Fujitsuka, M.; Toba, Y.; Moriyama, H.; Ito, O. J. Chem. Soc., Perkin Trans. 2 1999, 551.
64. (a) Hatchard, C.G.; Parker, C.A. Proc. R. Soc. London, Set. A 1956, 235, 518.
65. (b) Calvert, J.G.; Pitts, J.N. In Photochemistry; Wiley: New Tork, 1966; p 783.
66. Lawson, D.R.; Feldheim, D.L.; Foss, C.A.; Dorhout, P.K.; Elliot, C.M.; Martin, C.R.; Parkinson, B. J. Electrochem. Soc. 1992, 139, L68.
67. Lion, Y.; Delmelle, M.; Van De Vorst, A. Nature 1976, 263, 442.
68. Ohlendorf, V.; Willnow, A.; Hungerbühler, H.; Guldi, D.M.; Asmus, K.-D. J. Chem. Soc., Chem. Commun. 1995, 759.
69. Sawyer, D.T.; Roberts, J.L., Jr. Acc. Chem. Res. 1988, 21, 469.
70. 60 by an NADH model compound has been established previously, see: ref 17b.
71. Fukuzumi, S.; Suenobu, T.; Hirasaka, T.; Sakurada, N.; Arakawa, R.; Fujitsuka, M.; Ito, O. J. Phys. Chem. A 1999, 103, 5935.
72. For the derivation, see the Supporting Information.
73. (a) Marcus, R.A. Annu. Rev. Phys. Chem. 1964, 15, 155.
74. (b) Marcus, R.A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1111.
75. Fukuzumi, S.; Nakanishi, I.; Tanaka, K.; Suenobu, T.; Tabard, A.; Guilard, R.; Van Caemelbecke, E.; Kadish, K.M. J. Am. Chem. Soc. 1999, 121, 785.
76. Fukuzumi, S.; Nakanishi, I.; Suenobu, T.; Kadish, K.M. J. Am. Chem. Soc. 1999, 121, 3468.
77. Lind, J.; Shen, X.; Merényi, G.; Jonsson, B.Ö. J. Am. Chem. Soc. 1989, 111, 7654.
78. Peters, G.; Rodgers, M.A. J. Biochim. Biophys. Acta 1981, 637, 43.
79. (a) Foote, C.S. Acc. Chem. Res. 1968, 1, 104.
80. (b) Kearns, D.R. Chem. Rev. 1971, 71, 395.
81. (c) Stephenson, L.M.; Grdina, M.J.; Orfanopoulos, M. Acc. Chem. Res. 1980, 13, 419.
82. (d) Foote, C.S.; Clennan, E.L. Properties and Reactions of Singlet Oxygen. In Active Oxygen in Chemistry; Foote, C.S., Valentine, J.S., Greenberg, A., Liebman, J.F., Eds.; Chapman and Hall: London, 1995; pp 105-140.
83. Wilkinson, F.; Helman, W.P.; Ross, A.B. J. Phys. Chem. Ref. Data 1995, 24, 663.
84. Willson, R.L. Chem. Commun. 1970, 1005.
85. (a) Eliot, H.; Gianni, L.; Myers, C. Biochemistry 1984, 23, 928.
86. (b) Nagai, K.; Hecht, S.M. J. Biol. Chem. 1991, 266, 23994.
87. (c) Parraga, A.; Orozco, M.; Portugal, J. Eur. J. Biochem. 1992, 208, 227.
88. (a) von Sonntag, C. The Chemical Basis of Radiation Biology; Talor & Francis: London, 1987.
89. (b) Pogozelski, W.K.; Tullius, T.D. Chem. Rev. 1998, 98, 1089.
90. (c) Burrows, C.J.; Muller, J.G. Chem. Rev. 1998, 98, 1109.
91. (d) Armitage, B. Chem. Rev. 1998, 98, 1171.
92. (a) Mitra, K.; Kim, W.; Daniels, J.S.; Gates, K.S. J. Am. Chem. Soc. 1997, 119, 11691.
93. (b) Behroozi, S.J.; Kim, W.; Dannaldson, J.; Gates, K.S. Biochemistry 1996, 35, 1768.