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双链DNA中鸟嘌呤氧化产物的分析以及单链、双链或四链DNA中鸟嘌呤氧化途径的提出。

Analysis of guanine oxidation products in double-stranded DNA and proposed guanine oxidation pathways in single-stranded, double-stranded or quadruplex DNA.

作者信息

Morikawa Masayuki, Kino Katsuhito, Oyoshi Takanori, Suzuki Masayo, Kobayashi Takanobu, Miyazawa Hiroshi

机构信息

Kagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan.

Faculty of Science, Department of Chemistry, Shizuoka University, 836 Ohya, Suruga, Shizuoka 422-8529, Japan.

出版信息

Biomolecules. 2014 Feb 10;4(1):140-59. doi: 10.3390/biom4010140.

DOI:10.3390/biom4010140
PMID:24970209
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4030987/
Abstract

Guanine is the most easily oxidized among the four DNA bases, and some guanine-rich sequences can form quadruplex structures. In a previous study using 6-mer DNA d(TGGGGT), which is the shortest oligomer capable of forming quadruplex structures, we demonstrated that guanine oxidation products of quadruplex DNA differ from those of single-stranded DNA. Therefore, the hotooxidation products of double-stranded DNA (dsDNA) may also differ from that of quadruplex or single-stranded DNA, with the difference likely explaining the influence of DNA structures on guanine oxidation pathways. In this study, the guanine oxidation products of the dsDNA d(TGGGGT)/d(ACCCCA) were analyzed using HPLC and electrospray ionization-mass spectrometry (ESI-MS). As a result, the oxidation products in this dsDNA were identified as 2,5-diamino-4H-imidazol-4-one (Iz), 8-oxo-7,8-dihydroguanine (8oxoG), dehydroguanidinohydantoin (Ghox), and guanidinohydantoin (Gh). The major oxidation products in dsDNA were consistent with a combination of each major oxidation product observed in single-stranded and quadruplex DNA. We previously reported that the kinds of the oxidation products in single-stranded or quadruplex DNA depend on the ease of deprotonation of the guanine radical cation (G•+) at the N1 proton. Similarly, this mechanism was also involved in dsDNA. Deprotonation in dsDNA is easier than in quadruplex DNA and more difficult in single-stranded DNA, which can explain the formation of the four oxidation products in dsDNA.

摘要

鸟嘌呤是四种DNA碱基中最易被氧化的，一些富含鸟嘌呤的序列可形成四链体结构。在先前一项使用6聚体DNA d(TGGGGT)（能够形成四链体结构的最短寡聚物）的研究中，我们证明了四链体DNA的鸟嘌呤氧化产物与单链DNA的不同。因此，双链DNA（dsDNA）的光氧化产物可能也与四链体或单链DNA的不同，这种差异可能解释了DNA结构对鸟嘌呤氧化途径的影响。在本研究中，使用高效液相色谱法和电喷雾电离质谱法（ESI-MS）分析了dsDNA d(TGGGGT)/d(ACCCCA)的鸟嘌呤氧化产物。结果，该dsDNA中的氧化产物被鉴定为2,5-二氨基-4H-咪唑-4-酮（Iz）、8-氧代-7,8-二氢鸟嘌呤（8oxoG）、脱氢胍基乙内酰脲（Ghox）和胍基乙内酰脲（Gh）。dsDNA中的主要氧化产物与在单链和四链体DNA中观察到的每种主要氧化产物的组合一致。我们先前报道过，单链或四链体DNA中氧化产物的种类取决于鸟嘌呤自由基阳离子（G•+）在N1质子处去质子化的难易程度。同样，这种机制也在dsDNA中起作用。dsDNA中的去质子化比四链体DNA中更容易，比单链DNA中更难，这可以解释dsDNA中四种氧化产物的形成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9b1/4030987/45d4ee72a5b5/biomolecules-04-00140-g014.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9b1/4030987/5e7e81a328ff/biomolecules-04-00140-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9b1/4030987/52819e4cb94c/biomolecules-04-00140-g008.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9b1/4030987/6f255e098e10/biomolecules-04-00140-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9b1/4030987/c3a3e5f0dd85/biomolecules-04-00140-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9b1/4030987/77d69eb44b2f/biomolecules-04-00140-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9b1/4030987/0b69bb0231de/biomolecules-04-00140-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9b1/4030987/45247b0c1c2d/biomolecules-04-00140-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9b1/4030987/45d4ee72a5b5/biomolecules-04-00140-g014.jpg

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