A new trick (hydroxyl radical generation) for an old vitamin (B 12)

Journal of the American Chemical Society

Volumn 133, Issue 7, 2011, Pages 2148-2150

  Shell, Thomas A ^a   Lawrence, David S ^a  

^a UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC FORMATION; DNA CLEAVAGE; DNA STRANDS; HYDROXOCOBALAMIN; HYDROXYL RADICAL GENERATION; HYDROXYL RADICALS; PLASMID DNA; RADICAL SCAVENGING; TEMPORAL CONTROLS;

NUCLEIC ACIDS; PHOTOLYSIS; RESINS;

DNA;

2 DEOXYRIBOSE; CYANOCOBALAMIN; HYDROXIDE; HYDROXOCOBALAMIN; HYDROXYL RADICAL; PLASMID DNA;

ARTICLE; CATALYSIS; DNA CLEAVAGE; DNA DAMAGE; DNA STRAND; LIGHT; PHOTOLYSIS;

CATALYSIS; HYDROXYL RADICAL; LIGHT; MOLECULAR STRUCTURE; VITAMIN B 12;

EID: 79951832915     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja111585c     Document Type: Article

References (36)

1. Tullius, T. D. Radiat. Res., Proc. Int. Congr., 11th 2000, 2, 333.
2. (a) Jain, S. S.; Tullius, T. D. Nat. Protoc. 2008, 3, 1092.
3. (b) Frazee, R. W.; Taylor, J. A.; Tullius, T. D. J. Mol. Biol. 2002, 323, 665.
4. (c) Zaychikov, E.; Schickor, P.; Denissova, L.; Heumann, H. Methods Mol. Biol. 2001, 148, 49.
5. Trauger, J. W.; Dervan, P. B. Methods Enzymol. 2001, 340, 450.
6. Ciesienski, K. L.; Haas, K. L.; Dickens, M. G.; Tesema, Y. T.; Franz, K. J. J. Am. Chem. Soc. 2008, 130, 12246.
7. (a) Haruna, S.; Kuroi, R.; Kajiwara, K.; Hashimoto, R.; Matsugo, S.; Tokumaru, S.; Kojo, S. Bioorg. Med. Chem. Lett. 2002, 12, 675.
8. (b) Adam, W.; Cadet, J.; Dall'Acqua, F.; Epe, B.; Ramaiah, D.; Saha-Moeller, C. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 107.
9. (c) Matsugo, S.; Kawanishi, S.; Yamamoto, K.; Sugiyama, H.; Matsuura, T.; Saito, I. Angew. Chem., Int. Ed. Engl. 1991, 30, 1351.
10. (d) Aveline, B. M.; Matsugo, S.; Redmond, R. W. J. Am. Chem. Soc. 1997, 119, 11785.
11. (e) Tobin, D.; Arvanitidis, M.; Bisby, R. H. Biochem. Biophys. Res. Commun. 2002, 299, 155.
12. (f) Kitano, H.; Maeda, Y.; Furukawa, K.; Yamamoto, T.; Izumida, R.; Matsugo, S. Photochem. Photobiol. 1995, 62, 809.
13. (g) Guptasarma, P.; Balasubramanian, D.; Matsugo, S.; Saito, I. Biochemistry 1992, 31, 4296.
14. (h) Takeuchi, T.; Matsugo, S.; Morimoto, K. Carcinogenesis 1997, 18, 2051.
15. (a) Chang, C.-Y.; Hsieh, Y.-H.; Hsieh, L.-L.; Yao, K.-S.; Cheng, T.-C. J. Hazard. Mater. 2009, 166, 897.
16. (b) Matthews, R. H. J. Chem. Soc., Chem. Commun. 1983, 177.
17. (a) Trouiller, B.; Reliene, R.; Westbrook, A.; Solaimani, P.; Schiestl, R. H. Cancer Res. 2009, 69, 8784.
18. (b) Gurr, J.-R.; Wang, A. S. S.; Chen, C.-H.; Jan, K.-Y. Toxicology 2005, 213, 66.
19. (a) Adilakshmi, T.; Soper, S. F. C.; Woodson, S. A. Methods Enzymol. 2009, 468, 239.
20. (b) Brenowitz, M.; Chance, M. R.; Dhavan, G.; Takamoto, K. Curr. Opin. Struct. Biol. 2002, 12, 648.
21. Ottinger, L. M.; Tullius, T. D. J. Am. Chem. Soc. 2000, 122, 5901.
22. (a) Taylor, R.; Smucker, L.; Hanna, M. L.; Gill, J. Arch. Biochem. Biophys. 1973, 156, 521.
23. (b) Schrauzer, G. N.; Lee, L.-P.; Sibert, J. W. J. Am. Chem. Soc. 1970, 92, 2997.
24. Shell, T. A.; Mohler, D. L. Curr. Org. Chem. 2007, 11, 1525.
25. Morelli, R.; Russo-Volpe, S.; Bruno, N.; Scalzo, R. L. J. Agric. Food Chem. 2003, 51, 7418.
26. Beauchamp, C.; Fridovich, I. J. Biol. Chem. 1970, 245, 4641.
27. Halliwell, B.; Gutteridge, J. M. C.; Aruoma, O. I. Anal. Biochem. 1987, 165, 215.
28. (a) Gutteridge, J. M. C. FEBS Lett. 1981, 128, 343.
29. (b) Cheeseman, K. H.; Beavis, A.; Esterbauer, H. Biochem. J. 1988, 252, 64.
30. (c) Gutteridge, J. M. C.; Halliwell, B. Biochem. J. 1988, 253, 932.
31. (a) Mohler, D. L.; Downs, J. R.; Hurley-Predecki, A. L.; Sallman, J. R.; Gannett, P. M.; Shi, X. J. Org. Chem. 2005, 70, 909.
32. (b) Mohler, D. L.; Dain, D. R.; Kerekes, A. D.; Nadler, W. R.; Scott, T. L. Bioorg. Med. Chem. Lett. 1998, 8, 871.
33. Connolly, T. J.; Baldovi, M. V.; Mohtat, N.; Scaiano, J. C. Tetrahedron Lett. 1996, 37, 4919.
34. Povirk, L. F.; Wübker, W.; Köhnlein, W.; Hutchinson, F. Nucleic Acids Res. 1977, 4, 3573.
35. Kapp, P. D. Biochemistry 1984, 23, 4821.
36. Lee, H.-M.; Larson, D. R.; Lawrence, D. S. ACS Chem. Biol. 2009, 4, 409.