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http://dx.doi.org/10.5012/bkcs.2009.30.12.2949

Deguanylation of Guanine Based-Nucleosides and Calf Thymus DNA Induced by Halogenated Alkanes at the Physiological Condition  

Sherchan, Jyoti (College of Pharmacy, Yeungnam University)
Lee, Eung-Seok (College of Pharmacy, Yeungnam University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.12, 2009 , pp. 2949-2958 More about this Journal
Abstract
Massive deguanylation of guanine based-nucleosides induced by halogenated alkanes at the physiological condition have been observed. For the study of deguanylation effects by the different substituents and/or functionality in halogenated alkanes, diverse kinds of halogenated alkanes were incubated with guanine based-nucleosides (ddG, dG and guanosine) 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 deguanylation of nucleosides by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane. The order of deguanylation 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 deguanylation in guanine basednucleosides induced by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane at the physiological condition were investigated. Deguanylation 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.
Keywords
Deguanylation; Depurination; Halogenated alkanes; Guanine base-nucleosides; Calf thymus DNA;
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1 Kunkel, T. A. Proc. Natl. Acad. Sci. USA 1984, 81, 1494   DOI   ScienceOn
2 Vousden, K. H.; Bos, J. L.; Marsheall, C. J.; Phillips, D. H. Proc. Natl. Acad. Sci. USA 1986, 83, 1222   DOI   ScienceOn
3 Drake, J. W.; Baltz, R. H. Annu. Rev. Biochem. 1976, 45, 11   DOI   ScienceOn
4 Schaaper, R. M.; Leob, L. A. Proc. Natl. Acad. Sci. USA 1981, 78, 1773   DOI   ScienceOn
5 Lucas, L. T.; Gatehouse, D.; Shuker, D. E. G. J. Biol. Chem. 1999, 274, 18319   DOI
6 Sherchan, J.; Choi, H.; Lee, E. S. Bull. Korean Chem. Soc. 2009, 30(10), 2309   과학기술학회마을   DOI   ScienceOn
7 Sherchan, J.; Yun, M.; Lee, E. S. Bull. Korean Chem. Soc. 2009, 30(10), 2318   과학기술학회마을   DOI   ScienceOn
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   DOI   ScienceOn
10 Jones, A. R.; Wells, G. Xenobiotica. 1981, 11, 541   DOI   ScienceOn
11 James, S. P.; Pue, M. A.; Richards, D. H. Toxicol. Lett. 1981, 8, 7   DOI   ScienceOn
12 Tachizawa, H.; MacDonald, T. L.; Neal, R. A. Mol. Pharmacol. 1982, 22, 745
13 Zoltewicz, J. A.; Clark, D. F.; Sharpless, T. W.; Grahe, G. J. Am. Chem. Soc. 1970, 92, 1741   DOI
14 Volp, R. F.; Sipes, I. G.; Falcoz, C.; Carter, D. E.; Gross, J. F. Toxicol. Appl. Pharmacol. 1984, 75, 8   DOI   ScienceOn
15 Pearson, P. G.; Søderlund, E. J.; Dybing, E.; Nelson, S. D. Biochemistry 1990, 29, 4971   DOI   ScienceOn
16 Cmarik, J. L.; Inskeep, P. B.; Meredith, M. J.; Meyer, D. J.; Ketterer, B.; Guengerich, F. P. Cancer Res. 1990, 50, 2747
17 York, J. L. J. Org. Chem. 1981, 46, 2171   DOI
18 Garrett, E. R.; Mehta, P. J. J. Am. Chem. Soc. 1972, 94, 8542   DOI
19 Pearson, P. G.; Omichinski, J. G.; Myers, T. G.; Søderlund, E. J.; Dybing, E.; Nelson, S. D. Chem. Res. Toxicol. 1990, 3, 458   DOI   ScienceOn
20 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; vol. 10, p. 139