Sequence-specific electron injection into DNA from an intermolecular electron donor

Nucleic Acids Research

Volumn 41, Issue 8, 2013, Pages 4724-4728

  Morinaga, Hironobu ^a   Takenaka, Tomohiro ^a   Hashiya, Fumitaka ^a   Kizaki, Seiichiro ^a   Hashiya, Kaori ^a   Bando, Toshikazu ^a   Sugiyama, Hiroshi ^a,b,c  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 BROMOURACIL; HYDROGEN; OLIGONUCLEOTIDE; POLYAMIDE; PYRENE PYRROLE IMIDAZOLE POLYAMIDE CONJUGATE; UNCLASSIFIED DRUG; URACIL;

ARTICLE; BASE PAIRING; BINDING SITE; DNA DAMAGE; DNA DETERMINATION; DNA SEQUENCE; DNA TRANSFER; ELECTRON TRANSPORT; MOLECULAR MECHANICS; PRIORITY JOURNAL; SYNTHESIS;

BASE SEQUENCE; BROMOURACIL; DNA; ELECTRONS; IMIDAZOLES; NYLONS; PYRENES; PYRROLES;

EID: 84877308202     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gkt123     Document Type: Article

References (25)

1. Rogozin, I.B. and Pavlov, Y.I. (2003) Theoretical analysis of mutation hotspots and their DNA sequence context specificity. Mutat. Res., 544, 65-85.
2. Delaney, S. and Barton, J.K. (2003) Long-range DNA charge transport. J. Org. Chem., 68, 6475-6483.
3. Hall, D.B., Holmlin, R.E. and Barton, J.K. (1996) Oxidative DNA damage through long-range electron transfer. Nature, 382, 731-735.
4. Carell, T., Burgdorf, L.T., Kundu, L.M. and Cichon, M. (2001) The mechanism of action of DNA photolyases. Curr. Opin. Chem. Biol., 5, 491-498.
5. Sancer, G.B., Jorns, M.S., Payne, G., Fluke, D.J., Rupert, C.S. and Sancar, A. (1987) Action Mechanism of Escherichia coli DNA Photolyase. J. Biol. Chem., 262, 492-498.
6. Guo, X., Gorodetsky, A.A, Hone, J., Barton, J.K. and Nuckolls, C. (2008) Conductivity of a single DNA duplex bridging a carbon nanotube gap. Nat. Nanotechnol., 3, 163-167.
7. Li, Y., Kaneko, T., Hirotsu, Y. and Hatakeyama, R. (2010) Light-induced electron transfer through DNA-decorated single-walled carbon nanotubes. Small, 6, 27-30.
8. Kaden, P., Mayer-Enthart, E., Trifonov, A., Fiebig, T. and Wagenknecht, H.A. (2005) Real-time spectroscopic and chemical probing of reductive electron transfer in DNA. Angew. Chem. Int. Ed. Engl., 44, 1636-1639.
9. Seeman, N.C. (2005) From genes to machines: DNA nanomechanical devices. Trends Biochem. Sci., 30, 119-125.
10. Ito, T. and Rokita, S.E. (2003) Excess electron transfer from an internally conjugated aromatic amine to 5-bromo-20-deoxyuridine in DNA. J. Am. Chem. Soc., 125, 11480-11481.
11. Tashiro, R., Ohtsuki, A. and Sugiyama, H. (2010) The distance between donor and acceptor affects the proportion of C10 and C20 oxidation products of DNA in a BrU-containing excess electron transfer system. J. Am. Chem. Soc., 132, 14361-14363.
12. Giese, B. (2002) Long-distance electron transfer through DNA. Annu. Rev. Biochem., 71, 51-70.
13. Kelley, S.O., Jackson, N.M., Hill, M.G. and Barton, J.K. (1999) Long-Range electron transfer through DNA films. Angew. Chem. Int. Ed. Engl., 38, 941-945.
14. Behrens, C. and Burgdorf, L. (2002) Weak distance dependence of excess electron transfer in DNA. Angew. Chem. Int. Ed. Engl., 114, 1841-1844.
15. Messer, A., Carpenter, K., Forzley, K., Buchanan, J., Yang, S., Razskazovskii, Y., Cai, Z. and Sevilla, M.D. (2000) Electron spin resonance study of electron transfer rates in DNA: determination of the tunneling constant b for single-step excess electron transfer. J. Phys. Chem. B, 104, 1128-1136.
16. Boon, E.M., Ceres, D.M., Drummond, T.G., Hill, M.G. and Barton, J.K. (2000) Mutation detection by electrocatalysis at DNA-modified electrodes. Nat. Biotechnol., 18, 1096-1100.
17. Giese, B., Carl, B., Carl, T., Carell, T., Behrens, C., Hennecke, U., Schiemann, O. and Feresin, E. (2004) Excess electron transport through DNA: a single electron repairs more than one UV-induced lesion. Angew. Chem. Int. Ed. Engl., 43, 1848-1851.
18. Bando, T. and Sugiyama, H. (2006) Synthesis and biological properties of sequence-specific DNA-alkylating pyrrole-imidazole polyamides. Acc. Chem. Res., 39, 935-944.
19. Best, T.P., Edelson, B.S., Nickols, N.G. and Dervan, P.B. (2003) Nuclear localization of pyrrole-imidazole polyamide-fluorescein conjugates in cell culture. Proc. Natl Acad. Sci. USA, 100, 12063-12068.
20. Fujimoto, J., Bando, T., Minoshima, M., Kashiwazaki, G., Nishijima, S., Shinohara, K. and Sugiyama, H. (2008) Perylene-conjugated pyrrole polyamide as a sequence-specific fluorescent probe. Bioorg. Med. Chem., 16, 9741-9744.
21. Dervan, P.B. and Edelson, B.S. (2003) Recognition of the DNA minor groove by pyrrole-imidazole polyamides. Curr. Opin. Struct. Biol., 13, 284-299.
22. Watanabe, T., Tashiro, R. and Sugiyama, H. (2007) Photoreaction at 50-(G/C)AA(Br)UT-30 sequence in duplex DNA: efficient generation of uracil-5-yl radical by charge transfer. J. Am. Chem. Soc., 129, 8163-8168.
23. Xu, Y., Tashiro, R. and Sugiyama, H. (2007) Photochemical determination of different DNA structures. Nat. Protoc., 2, 78-87.
24. Tashiro, R., Wang, A.H. and Sugiyama, H. (2006) Photoreactivation of DNA by an archaeal nucleoprotein Sso7d. Proc. Natl Acad. Sci. USA, 103, 16655-16659.
25. Oyoshi, T., Wang, A.H. and Sugiyama, H. (2002) Photoreactivity of 5-iodouracil-containing DNA-Sso7d complex in solution: the protein-induced DNA kink causes intrastrand hydrogen abstraction from the 5-methyl of thymine at the 50 side. J. Am. Chem. Soc., 124, 2086-2087.