Suzuki T, Yamada M, Ide H, Kanaori K, Tajima K, Morii T, Makino K
Institute of Advanced Energy, Kyoto University, Gokasho, Uji 611-0011, Japan.
Chem Res Toxicol. 2000 Apr;13(4):227-30. doi: 10.1021/tx990164x.
2'-Deoxyoxanosine (dOxo) is a novel DNA lesion produced from dGuo by reaction with nitrous acid or nitric oxide [Suzuki, T., Yamaoka, R., Nishi, M., Ide, H., and Makino, K. (1996) J. Am. Chem. Soc. 118, 2515-2516]. We investigated the reaction of dOxo with glycine (Gly) under physiological conditions. When 5 mM dOxo was incubated with 500 mM Gly in 100 mM sodium phosphate buffer (pH 7.4) at 37 degrees C, an unknown product was formed exclusively. The yield of the product was 86% at an incubation time of 3 h. Using spectrometric data, it was identified as a ring-opened adduct containing an amide bond between the carbonyl group of dOxo and the amino group of Gly. The adduct was very stable (t(1/2) = 1280 h) under physiological conditions. Furthermore, dOxo in oligodeoxynucleotide reacted with Gly, yielding the same adduct. These results suggest that dOxo formed in DNA may react with Gly present in cells, resulting in adduct formation in vivo.
2'-脱氧氧杂鸟苷（dOxo）是由脱氧鸟苷（dGuo）与亚硝酸或一氧化氮反应产生的一种新型DNA损伤产物[铃木，T.，山冈，R.，西，M.，井手，H.，以及牧野，K.（1996年）《美国化学会志》118，2515 - 2516]。我们研究了在生理条件下dOxo与甘氨酸（Gly）的反应。当在37℃下，将5 mM的dOxo与500 mM的Gly在100 mM磷酸钠缓冲液（pH 7.4）中孵育时，仅形成了一种未知产物。在孵育3小时时，该产物的产率为86%。利用光谱数据，它被鉴定为一种开环加合物，在dOxo的羰基与Gly的氨基之间含有一个酰胺键。该加合物在生理条件下非常稳定（半衰期 = 1280小时）。此外，寡脱氧核苷酸中的dOxo与Gly反应，产生相同的加合物。这些结果表明，在DNA中形成的dOxo可能与细胞中存在的Gly反应，导致在体内形成加合物。
