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Mechanism of 1,N2-etheno-2'-deoxyguanosine formation from epoxyaldehydes.由环氧醛生成1,N2-乙烯基-2'-脱氧鸟苷的机制。
Chem Res Toxicol. 2007 Nov;20(11):1685-92. doi: 10.1021/tx7001433. Epub 2007 Oct 2.
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4-Hydroperoxy-2-nonenal-induced formation of 1,N2-etheno-2'-deoxyguanosine adducts.4-氢过氧-2-壬烯醛诱导形成1,N2-乙烯基-2'-脱氧鸟苷加合物。
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4
Dioxododecenoic acid: a lipid hydroperoxide-derived bifunctional electrophile responsible for etheno DNA adduct formation.二氧代十二碳烯酸：一种源自脂质氢过氧化物的双功能亲电试剂，负责形成乙烯基DNA加合物。
Chem Res Toxicol. 2005 Mar;18(3):566-78. doi: 10.1021/tx049716o.
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Structural characterization of an etheno-2'-deoxyguanosine adduct modified by tetrahydrofuran.由四氢呋喃修饰的乙烯基-2'-脱氧鸟苷加合物的结构表征
Chem Res Toxicol. 2005 Feb;18(2):290-9. doi: 10.1021/tx0497494.
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Coupling products of nucleosides with the glyoxal adduct of deoxyguanosine.核苷与脱氧鸟苷乙二醛加合物的偶联产物。
Chem Res Toxicol. 2004 Aug;17(8):1047-56. doi: 10.1021/tx049906z.
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Predominance of the 1,N2-propano 2'-deoxyguanosine adduct among 4-hydroxy-2-nonenal-induced DNA lesions.在4-羟基-2-壬烯醛诱导的DNA损伤中，1,N2-丙烷-2'-脱氧鸟苷加合物占主导地位。
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8
Induction of apoptosis in colorectal carcinoma cells treated with 4-hydroxy-2-nonenal and structurally related aldehydic products of lipid peroxidation.用4-羟基-2-壬烯醛及脂质过氧化反应产生的结构相关醛类产物处理结肠癌细胞后诱导其凋亡。
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Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal.含有脂质过氧化产物反式-4-羟基壬烯醛的立体化学定义的1,N2-脱氧鸟苷加合物的寡核苷酸的位点特异性合成及反应活性。
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10
4-Hydroxy-2-nonenal: a product and mediator of oxidative stress.4-羟基-2-壬烯醛：氧化应激的产物与介质
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合成 2,3-环氧-4-羟基壬醛的四个立体异构体及其与脱氧鸟苷的反应性。

Synthesis of the four stereoisomers of 2,3-epoxy-4-hydroxynonanal and their reactivity with deoxyguanosine.

机构信息

Department of Chemistry, Center in Molecular Toxicology, Vanderbilt University, VU Station B 351822, Nashville, Tennessee, 37235-1822, USA.

出版信息

Org Biomol Chem. 2011 Mar 21;9(6):1960-71. doi: 10.1039/c0ob00546k. Epub 2011 Jan 24.

DOI:10.1039/c0ob00546k
PMID:21258716
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3694406/
Abstract

2,3-Epoxy-4-hydroxynonanal (EHN) is a potential product of lipid peroxidation that gives rise to genotoxic etheno adducts. We have synthesized all four stereoisomers of EHN and individually reacted them with 2'-deoxyguanosine. In addition to 1,N(2)-etheno-2'-deoxyguanosine, 12 stereoisomeric products were isolated and characterized by (1)H NMR and circular dichroism spectroscopy. The stereochemical assignments were consistent with selective NOE spectra, vicinal coupling constants, and molecular mechanics calculations. Reversed-phase HPLC conditions were developed that could separate most of the adduct mixture.

摘要

2,3-环氧-4-羟基壬醛（EHN）是脂质过氧化的潜在产物，会导致遗传毒性乙稀加合物的形成。我们已经合成了 EHN 的全部四个立体异构体，并分别与 2'-脱氧鸟苷反应。除了 1,N(2)-乙稀-2'-脱氧鸟苷外，还分离和鉴定了 12 个立体异构体产物，通过（1）H NMR 和圆二色性光谱进行鉴定。立体化学的分配与选择性 NOE 光谱、邻位耦合常数和分子力学计算一致。开发了反相 HPLC 条件，可以分离大部分加合物混合物。