Characterization of 2'-deoxyadenosine adducts derived from 4-oxo-2-nonenal, a novel product of lipid peroxidation.
Characterization of 2'-deoxyadenosine adducts derived from 4-oxo-2-nonenal, a novel product of lipid peroxidation.
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源自 4-oxo-2-nonenal（脂质过氧化的新产物）的 2-脱氧腺苷加合物的表征。
DOI：
10.1021/tx000057z
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发表时间：
2000
影响因子：
4.1
通讯作者：
Blair,IA
中科院分区：
文献类型：
--
作者：
Lee,SH;Rindgen,D;BibleJr,RH;Hajdu,E;Blair,IA
通过液相色谱/质谱分析2 ' -脱氧腺苷与4-氧-2-壬烯醛之间的反应，发现存在三个主要产物（A1， A2和B）。加合物a1和a2是同分异构体；它们在室温下相互转化，并且都很容易脱水形成加合物B。通过碰撞诱导解离和多重串联质谱联用得到的加合物B的质谱特征与取代的乙烯加合物的质谱特征一致。核磁共振波谱表明B的结构与取代的乙烯-2 ' -脱氧腺苷加合物1 ' ' -[3-（2 ' -脱氧-β-d-红五氟脲基）- 3h -咪唑[2,1-i]嘌呤-7-基]庚烷-2 ' ' - 1一致。结构的明确证据来自于加合物a1和A2（加合物B的前体）与硼氢化钠的反应。加合物a1和a2都形成了相同的还原产物，其中含有8个额外的氢原子。该还原产物的质谱特征表明，2 ' -脱氧腺苷的外环氨基（N6）与4-氧-2-壬烯醛的C-1相连。4-氧-2-壬烯醛与小牛胸腺DNA的反应也可生成取代的乙醇加合物a1和A2以及取代的乙烯加合物B，加合物B的生成量几乎比加合物a1和A2大2个数量级。这与观察到的加合物的稳定性是一致的。这项研究提供了额外的证据，表明4-氧-2-壬烯醛与DNA有效地反应形成取代的乙二烯加合物。
Analysis of the reaction between 2‘-deoxyadenosine and 4-oxo-2-nonenal by liquid chromatography/mass spectrometry revealed the presence of three major products (adducts A1, A2, and B). Adducts A1and A2were isomeric; they interconverted at room temperature, and they each readily dehydrated to form adduct B. The mass spectral characteristics of adduct B obtained by collision-induced dissociation coupled with multiple tandem mass spectrometry were consistent with those expected for a substituted etheno adduct. The structure of adduct B was shown by NMR spectroscopy to be consistent with the substituted etheno-2‘-deoxyadenosine adduct 1‘ ‘-[3-(2‘-deoxy-β-d-erythropentafuranosyl)-3H-imidazo[2,1-i]purin-7-yl]heptane-2‘ ‘-one. Unequivocal proof of structure came from the reaction of adducts A1and A2(precursors of adduct B) with sodium borohydride. Adducts A1and A2each formed the same reduction product, which contained eight additional hydrogen atoms. The mass spectral characteristics of this reduction product established that the exocyclic amino group (N6) of 2‘-deoxyadenosine was attached to C-1 of the 4-oxo-2-nonenal. The reaction of 4-oxo-2-nonenal with calf thymus DNA was also shown to result in the formation of substituted ethano adducts A1and A2and substituted etheno adduct B. Adduct B was formed in amounts almost 2 orders of magnitude greater than those of adducts A1and A2. This was in keeping with the observed stability of the adducts. The study presented here has provided additional evidence which shows that 4-oxo-2-nonenal reacts efficiently with DNA to form substituted etheno adducts.
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2,3-环氧-4-羟基壬醛与脱氧鸟苷反应形成的加合物的结构表征。
影响因子：
4.1
作者：
Sodum,RS;Chung,FL
通讯作者：
Chung,FL
腺嘌呤和其他碱与亚油酸甲酯氢过氧化物的二次氧化产物反应形成荧光产物。
DOI：
10.1271/bbb1961.53.1575
发表时间：
1989
期刊：
Agricultural and biological chemistry
影响因子：
--
作者：
K. Hasegawa;K. Fujimoto;T. Kaneda;W. Neff;E. Frankel
通讯作者：
E. Frankel
影响因子：
4.1
作者：
HECHT, SS;YOUNGSCIAME, R;CHUNG, FL
通讯作者：
CHUNG, FL
丙二醛与鸟嘌呤核苷的反应：在碱基配对区域形成含有恶二氮杂双环壬烯残基的加合物
DOI：
--
发表时间：
1986
期刊：
影响因子：
--
作者：
L. Marnett;A. Basu;S. O'hara;P. Weller;A. Rahman;J. Oliver
通讯作者：
J. Oliver
影响因子：
4.1
作者：
Barlow, T;Takeshita, J;Dipple, A
通讯作者：
Dipple, A