Rapid Communication in Photoscience

Korean Society of Photoscience (한국광과학회)
권호 표지
DOI QR코드

DOI QR Code

Regulation of DNAzyme function by hypoxic irradiation that induces one-electron reduction of 2-oxoalkyl group on thymine base

  • Kanezaki, Hiroshi (Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University) ;
  • Nishimoto, Sei-Ichi (Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University) ;
  • Tanabe, Kazuhito (Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University)
  • Received : 2014.12.08
  • Accepted : 2014.12.20
  • Published : 2014.12.31
Download PDF
⟨ Previous Next ⟩

Abstract

We characterized the one-electron reduction of oligodeoxynucleotides with a 2-oxopropyl group on a thymine base ($d^{oxo}T$) and applied the reaction to the radiolytic activation of DNAzyme function. We designed a system in which the DNAzyme function of cleaving mRNA was suppressed by introduction of $d^{oxo}T$ into the strand of DNAzyme. Hypoxic X-irradiation led to recovery of the cleavage ability because the 2-oxopropyl group was removed to form unmodified DNAzyme. We characterized the DNAzyme function by monitoring the fluorescence change of fluorophore- and quencher-labeled target strands. We confirmed that the DNAzyme function could be regulated by hypoxic X-irradiation and the reaction of $d^{oxo}T$.

Keywords

References

  1. Milligan, J. F.; Matteucci, M. D.; Martin, J. C. J. Med. Chem. 1993, 36, 1923-1937. https://doi.org/10.1021/jm00066a001
  2. Miyake, Y.; Togashi, H.; Tashiro, M.; Yamaguchi, H.; Oda, S.; Kudo, M.; Tanaka, Y.; Kondo, Y.; Sawa, R.; Fujimoto, T.; Machinami, T.; Ono, A. J. Am. Chem. Soc. 2006, 128, 2172-2173. https://doi.org/10.1021/ja056354d
  3. Meggers, E.; Holland, P. L.; Tolman, W. B.; Romesberg, F. E.; Schultz, P. G. J. Am. Chem. Soc. 2000, 122, 10714-10715. https://doi.org/10.1021/ja0025806
  4. Tanaka, K.; Tengeiji, A.; Kato, T.; Toyama, N.; Shionoya, M. Science 2003, 299, 1212-1213. https://doi.org/10.1126/science.1080587
  5. Wada, T.; Minamimoto, N.; Inaki, Y.; Inoue, Y. J. Am. Chem. Soc. 2000, 122, 6900-6910. https://doi.org/10.1021/ja9935456
  6. Krock, L.; Heckel, A. Angew. Chem. Int. Ed. 2005, 44, 471-473. https://doi.org/10.1002/anie.200461779
  7. Mayer, G.; Heckel, A. Angew. Chem. Int. Ed. 2006, 45, 4900-4921. https://doi.org/10.1002/anie.200600387
  8. Asanuma, H.; Ito, T.; Yoshida, T.; Liang, X.; Komiyama, M. Angew. Chem. Int. Ed. 1999, 38, 2393-2395. https://doi.org/10.1002/(SICI)1521-3773(19990816)38:16<2393::AID-ANIE2393>3.0.CO;2-7
  9. Spinks, J. W. T.; Wood, R. J. Introduction to Radiation Chemistry 3rd Ed.; Wiley-Interscience: New York, 1990.
  10. Tanabe, K.; Kanezaki, H.; Ishii, H.; Nishimioto, S. Org. Biomol. Chem. 2007, 5, 1242-1246. https://doi.org/10.1039/b618810a
  11. Tanabe, K.; Mimasu, Y.; Eto, A.; Tachi, Y.; Sakakibara, S.; Mori, M.; Hatta, H.; Nishimoto, S. Bioorg. Med. Chem. 2003, 11, 4551-4556. https://doi.org/10.1016/j.bmc.2003.08.001
  12. Hirata, N.; Fujisawa, Y.; Tanabe, K.; Harada, H.; Hiraoka, M.; Nishimoto, S. Org. Biomol. Chem. 2009, 7, 651-654. https://doi.org/10.1039/B816194A
  13. Tanabe, K.; Mizoe, T.; Sugiura, M.; Okada, K.; Nishimoto, S. Bioorg. Med. Chem. Lett. 2013, 23, 2098-2100. https://doi.org/10.1016/j.bmcl.2013.01.123
  14. Baum, D. A.; Silverman, S. K. Cell. Mol. Life Sci. 2008, 65, 2156-2174. https://doi.org/10.1007/s00018-008-8029-y
  15. Silverman, S. K. Chem. Commun. 2008, 3647-3485.
  16. Santoro, S. W.; Joyce, G. F. Biochemistry 1998, 37, 13330- 13342. https://doi.org/10.1021/bi9812221
  17. Hobartner, C.; Silverman, S. K. Biopolymers 2007, 87, 279-292. https://doi.org/10.1002/bip.20813
  18. Scherer, L. J.; Rossi, J. J. Nat. Biotechnol. 2003, 21, 1457-1465. https://doi.org/10.1038/nbt915
  19. Flintoft, L. Nat. Rev. Gen. 2008, 9, 6.
  20. Liu, J.; Lu, Y. J. Am. Chem. Soc. 2003, 125, 6642-6643. https://doi.org/10.1021/ja034775u
  21. Buxton, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 513-886. https://doi.org/10.1063/1.555805

Cited by

  1. Chemically Caged Nucleic Acids vol.46, pp.5, 2017, https://doi.org/10.1246/cl.161063