Browse > Article
http://dx.doi.org/10.5012/bkcs.2009.30.10.2318

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

Sherchan, Jyoti (College of Pharmacy, Yeungnam University)
Yun, Min-Ho (College of Pharmacy, Yeungnam University)
Lee, Eung-Seok (College of Pharmacy, Yeungnam University)
Publication Information
Abstract
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.
Keywords
Deadenylation; Depurination; Halogenated alkanes; Adenine base-nucleosides; Calf thymus DNA;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 1
연도 인용수 순위
1 Drake, J. W.; Baltz, R. H. Annu. Rev. Biochem. 1976, 45, 11.   DOI   ScienceOn
2 Schaaper, R. M.; Leob, L. A. Proc. Natl. Acad. Sci. USA 1981, 78, 1773.   DOI   ScienceOn
3 Lucas, L. T.; Gatehouse, D.; Shuker, D. E. G. J. Biol. Chem. 1999, 274, 18319.   DOI
4 Sherchan, J.; Choi, H.; Lee, E. S. Bull. Korean Chem. Soc. 2009, 30(10), 2309.   DOI   ScienceOn
5 Burlinson, N. E.; Lee, L. A.; Rosenblatt, D. H. Environ. Sci. Technol. 1982, 16, 627.   DOI   ScienceOn
6 Kunkel, T. A. Proc. Natl. Acad. Sci. USA 1984, 81, 1494.   DOI   ScienceOn
7 Vousden, K. H.; Bos, J. L.; Marsheall, C. J.; Phillips, D. H. Proc. Natl. Acad. Sci. USA 1986, 83, 1222.   DOI   ScienceOn
8 Pearson, P. G.; Omichinski, J. G.; Myers, T. G.; Soderlund, E. J.; Dybing, E.; Nelson, S. D. Chem. Res. Toxicol. 1990, 3, 458.   DOI   ScienceOn
9 Pearson, P. G.; Soderlund, E. J.; Dybing, E.; Nelson, S. D. Biochemistry 1990, 29, 4971   DOI   ScienceOn
10 Cmarik, J. L.; Inskeep, P. B.; Meredith, M. J.; Meyer, D. J.; Ketterer, B.; Guengerich, F. P. Cancer Res. 1990, 50, 2747.
11 Zoltewicz, J. A.; Clark, D. F.; Sharpless, T. W.; Grahe, G. J. Am. Chem. Soc. 1970, 92, 1741.   DOI
12 York, J. L. J. Org. Chem. 1981, 46, 2171.
13 Garrett, E. R.; Mehta, P. J. J. Am. Chem. Soc. 1972, 94, 8542.   DOI
14 James, S. P.; Pue, M. A.; Richards, D. H. Toxicol. Lett. 1981, 8, 7.   DOI   ScienceOn
15 Lag, M.; Omichinski, J. G.; Dybing, E.; Nelson, S. D.; Soderlund, E. J. Chem. Res. Toxicol. 1994, 93, 73.
16 Jones, A. R.; Fakhouri, G.; Gadiel, P. Experientia. 1979, 35, 1432.   DOI   ScienceOn
17 Jones, A. R.; Wells, G. Xenobiotica. 1981, 11, 541.   DOI   ScienceOn
18 Tachizawa, H.; MacDonald, T. L.; Neal, R. A. Mol. Pharmacol. 1982, 22, 745.
19 Volp, R. F.; Sipes, I. G.; Falcoz, C.; Carter, D. E.; Gross, J. F. Toxicol. Appl. Pharmacol. 1984, 75, 8.   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; 10,139.