DOI QR코드

DOI QR Code

Deadenylation of Adenine Based-Nucleosides and Calf thymus DNA Induced by Halogenated Alkanes at the Physiological Condition

  • 발행 : 2009.10.20

초록

Massive deadenylation of adenine based-nucleosides induced by halogenated alkanes at the physiological condition have been observed. For the study of deadenylation effects by the different substituents and/or functionality in halogenated alkanes, diverse kinds of halogenated alkanes were incubated with adenine based-nucleosides (ddA, dA and adenosine) for 48 h at the physiological condition (pH 7.4, $37\;{^{\circ}C}$), which were analyzed by HPLC and further confirmed by LC-MS. Among the sixteen different halogenated alkanes, we observed massive deadenylation of nucleosides by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane. The order of deadenylation rate was highest in 2-bromo-2-methylpropane followed by 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane. In addition, time and dose response relationship of deadenylation in adenine based-nucleosides induced by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane at the physiological condition were investigated. In addition, deadenylation of calf thymus DNA induced by halogenated alkanes was also investigated. These results suggest that the toxic effect of certain halogenated alkanes might be from the depurination of nucleosides.

키워드

참고문헌

  1. Kunkel, T. A. Proc. Natl. Acad. Sci. USA 1984, 81, 1494. https://doi.org/10.1073/pnas.81.5.1494
  2. Vousden, K. H.; Bos, J. L.; Marsheall, C. J.; Phillips, D. H. Proc. Natl. Acad. Sci. USA 1986, 83, 1222. https://doi.org/10.1073/pnas.83.5.1222
  3. Drake, J. W.; Baltz, R. H. Annu. Rev. Biochem. 1976, 45, 11. https://doi.org/10.1146/annurev.bi.45.070176.000303
  4. Schaaper, R. M.; Leob, L. A. Proc. Natl. Acad. Sci. USA 1981, 78, 1773. https://doi.org/10.1073/pnas.78.3.1773
  5. Lucas, L. T.; Gatehouse, D.; Shuker, D. E. G. J. Biol. Chem. 1999, 274, 18319. https://doi.org/10.1074/jbc.274.26.18319
  6. Sherchan, J.; Choi, H.; Lee, E. S. Bull. Korean Chem. Soc. 2009, 30(10), 2309. https://doi.org/10.5012/bkcs.2009.30.10.2309
  7. Burlinson, N. E.; Lee, L. A.; Rosenblatt, D. H. Environ. Sci. Technol. 1982, 16, 627. https://doi.org/10.1021/es00103a018
  8. Lag, M.; Omichinski, J. G.; Dybing, E.; Nelson, S. D.; Soderlund, E. J. Chem. Res. Toxicol. 1994, 93, 73.
  9. Jones, A. R.; Fakhouri, G.; Gadiel, P. Experientia. 1979, 35, 1432. https://doi.org/10.1007/BF01962767
  10. Jones, A. R.; Wells, G. Xenobiotica. 1981, 11, 541. https://doi.org/10.3109/00498258109045865
  11. James, S. P.; Pue, M. A.; Richards, D. H. Toxicol. Lett. 1981, 8, 7. https://doi.org/10.1016/0378-4274(81)90130-2
  12. Tachizawa, H.; MacDonald, T. L.; Neal, R. A. Mol. Pharmacol. 1982, 22, 745.
  13. Volp, R. F.; Sipes, I. G.; Falcoz, C.; Carter, D. E.; Gross, J. F. Toxicol. Appl. Pharmacol. 1984, 75, 8. https://doi.org/10.1016/0041-008X(84)90070-X
  14. Dybing, E.; Omichinski, J. G.; Saderlund, E. J.; Brunborg, G.; Lag, M.; Holme, J. A.; Nelson, S. D. Reviews in Biochemical Toxicology; Hodgson, E.; Bend, J. R.; Philpot, R. M., Eds.; Elsevier Science Publishing: New York, 1989; 10,139.
  15. Pearson, P. G.; Omichinski, J. G.; Myers, T. G.; Soderlund, E. J.; Dybing, E.; Nelson, S. D. Chem. Res. Toxicol. 1990, 3, 458. https://doi.org/10.1021/tx00017a012
  16. Pearson, P. G.; Soderlund, E. J.; Dybing, E.; Nelson, S. D. Biochemistry 1990, 29, 4971 https://doi.org/10.1021/bi00472a030
  17. Cmarik, J. L.; Inskeep, P. B.; Meredith, M. J.; Meyer, D. J.; Ketterer, B.; Guengerich, F. P. Cancer Res. 1990, 50, 2747.
  18. Zoltewicz, J. A.; Clark, D. F.; Sharpless, T. W.; Grahe, G. J. Am. Chem. Soc. 1970, 92, 1741. https://doi.org/10.1021/ja00709a055
  19. York, J. L. J. Org. Chem. 1981, 46, 2171.
  20. Garrett, E. R.; Mehta, P. J. J. Am. Chem. Soc. 1972, 94, 8542. https://doi.org/10.1021/ja00779a041

피인용 문헌

  1. Deguanylation of Guanine Based-Nucleosides and Calf Thymus DNA Induced by Halogenated Alkanes at the Physiological Condition vol.30, pp.12, 2009, https://doi.org/10.5012/bkcs.2009.30.12.2949