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8-氧代鸟苷和8-氧代-2'-脱氧鸟苷与2'-脱氧腺苷、2'-脱氧胞苷、2'-脱氧鸟苷和胸腺嘧啶的碱基配对。

Base pairing of 8-oxoguanosine and 8-oxo-2'-deoxyguanosine with 2'-deoxyadenosine, 2'-deoxycytosine, 2'-deoxyguanosine, and thymidine.

作者信息

Gannett P M, Sura T P

机构信息

School of Pharmacy, West Virginia University, Morgantown 26506.

出版信息

Chem Res Toxicol. 1993 Sep-Oct;6(5):690-700. doi: 10.1021/tx00035a015.

DOI:10.1021/tx00035a015
PMID:8292748
Abstract

Base pair formation between O-silyl derivatives of 8-oxoguanosine (8-OxoG) and 8-oxo-2'-deoxyguanosine (8-OxodG) with 2'-deoxyadenosine (dA), 2'-deoxycytosine (dC), 2'-deoxyguanosine (dG), and thymidine (dTHd) have been examined by NMR methods in chloroform. 8-OxoG and 8-OxodG form base pairs with all four nucleosides, suggesting that they can mimic the base pairing properties of any DNA base. In 8-OxodG.dA or 8-OxoG.dA base pairs both bases assume Hoogsteen geometry with respect to both bases. Hoogsteen and Watson-Crick base pairs are formed between 8-OxodG or 8-OxoG and either dThd or dG. Only Watson-Crick geometry is seen for 8-OxodG.dC and 8-OxoG.dC base pairs. In all base pairs the glycosidic bond of 8-OxodG or 8-OxoG is syn and anti for the base pair partner. Additional base pairing studies with the modified nucleosides 1-methyl-8-oxoguanosine (1-Me-8-oxoG), 7-methyl-8-oxoguanosine (7-Me-8-oxoG), and 8-methoxyguanosine (8-OMeG), modified nucleosides structurally related to 8-OxoG and 8-OxodG, support the proposed base pair structures and aided in the determination of base pair geometry. Association constants were determined for 8-OxoG.dN and 8-OxodG.dN (N = A, C, G, Thd) base pairs as well as the normal dTHd-A and dG.dC base pairs. The magnitude of the association constants allows the relative stabilities of the base pairs to be determined: 8-OxodGWC.dC (8-OxoGWC.dC) approximately dGWC.dC > 8-OxodGH.dG (8-OxoGH.dG) > 8-OxodGH.dA (8-OxoGH.dA) > 8-OxodGH.dThd (8-oxoGH.dThd) approximately dThd.dA. The formation of these base pairs is consistent with the known mutagenic nature of 8-oxo-2'-deoxyguanosine and with NMR studies of oligonucleotides containing the 8-oxoG modification.

摘要

采用核磁共振方法在氯仿中研究了8-氧代鸟苷（8-OxoG）和8-氧代-2'-脱氧鸟苷（8-OxodG）的O-硅烷基衍生物与2'-脱氧腺苷（dA）、2'-脱氧胞苷（dC）、2'-脱氧鸟苷（dG）和胸苷（dTHd）之间的碱基对形成情况。8-OxoG和8-OxodG与所有四种核苷形成碱基对，这表明它们可以模拟任何DNA碱基的碱基配对特性。在8-OxodG.dA或8-OxoG.dA碱基对中，两个碱基相对于彼此都呈现Hoogsteen几何构型。在8-OxodG或8-OxoG与dThd或dG之间形成了Hoogsteen碱基对和沃森-克里克碱基对。对于8-OxodG.dC和8-OxoG.dC碱基对，只观察到沃森-克里克几何构型。在所有碱基对中，8-OxodG或8-OxoG的糖苷键对于碱基对伙伴而言是顺式和反式的。对与8-OxoG和8-OxodG结构相关的修饰核苷1-甲基-8-氧代鸟苷（1-Me-8-oxoG）、7-甲基-8-氧代鸟苷（7-Me-8-oxoG）和8-甲氧基鸟苷（8-OMeG）进行的额外碱基配对研究，支持了所提出的碱基对结构，并有助于确定碱基对几何构型。测定了8-OxoG.dN和8-OxodG.dN（N = A、C、G、Thd）碱基对以及正常的dTHd-A和dG.dC碱基对的缔合常数。缔合常数的大小使得能够确定碱基对的相对稳定性：8-OxodGWC.dC（8-OxoGWC.dC）≈dGWC.dC > 8-OxodGH.dG（8-OxoGH.dG）> 8-OxodGH.dA（8-OxoGH.dA）> 8-OxodGH.dThd（8-oxoGH.dThd）≈dThd.dA。这些碱基对的形成与8-氧代-2'-脱氧鸟苷已知的诱变性质以及对含有8-oxoG修饰的寡核苷酸的核磁共振研究一致。

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