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首页> 外文期刊>Life sciences >FORMATION OF ADDUCTS BETWEEN 13-OXOOCTADECADIENOIC ACID (13-OXO) AND PROTEIN-DERIVED THIOLS, IN VIVO AND IN VITRO
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FORMATION OF ADDUCTS BETWEEN 13-OXOOCTADECADIENOIC ACID (13-OXO) AND PROTEIN-DERIVED THIOLS, IN VIVO AND IN VITRO

机译：体内和体外13-氧代十碳二烯酸（13-OXO）与蛋白质衍生的硫醇之间的形成

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摘要

Linoleic acid is metabolized by numerous tissues to oxidized derivatives possessing biological activity. In the current experiments we have investigated the reaction of 13-oxooctadecadienoic acid (13-OXO) and the metabolic precursor 13-hydroxyoctadecadienoic acid (13-HODE) with cellular macromolecules and model cellular nucleophiles. Colonic mucosal explants from Sprague-Dawley rats were incubated in the presence of [1-C-14]-13-OXO or [1-C-14]-13-HODE. The binding of radiolabel to the protein and nucleic acid fractions was analyzed by isopycnic centrifugation in Cs2SO4. Cellular homogenates incubated with either 13-OXO or 13-HODE resulted in the binding of radiolabel to cellular protein. No significant amounts of reaction with cellular RNA or DNA were observed. To assess possible modes of reaction with cellular constituents, the oxidized fatty acids were incubated in vitro with oxygen, sulfur, or nitrogen nucleophiles including, serine, cysteine, glutathione, methionine, lysine, adenosine, and guanosine. Under physiologic conditions, in the absence of cellular homogenates, only 13-OXO was reactive. In addition, only the sulfur-containing compounds cysteine and glutathione showed significant rates of reaction. Furthermore, treatment of colonic homogenates with N-ethylmaleimide reduced the binding of [1-C-14]-13-OXO to cellular protein. These data support the suggestion that 13-HODE requires metabolic activation, by dehydrogenation to 13-OXO, prior to binding to cellular protein and that protein-derived thiol groups are involved in the binding reactions. [References: 27]
机译：亚油酸被许多组织代谢为具有生物活性的氧化衍生物。在当前的实验中，我们已经研究了13-氧十八碳二烯酸（13-OXO）和代谢前体13-羟基十八碳二烯酸（13-HODE）与细胞大分子和模型细胞亲核试剂的反应。将来自Sprague-Dawley大鼠的结肠粘膜外植体在[1-C-14] -13-OXO或[1-C-14] -13-HODE的存在下孵育。通过在Cs2SO4中进行等温离心，分析了放射性标记与蛋白质和核酸部分的结合。用13-OXO或13-HODE孵育的细胞匀浆导致放射性标记与细胞蛋白结合。没有观察到与细胞RNA或DNA的大量反应。为了评估与细胞成分反应的可能模式，将氧化的脂肪酸与氧，硫或氮亲核试剂（包括丝氨酸，半胱氨酸，谷胱甘肽，蛋氨酸，赖氨酸，腺苷和鸟苷）进行体外孵育。在生理条件下，在没有细胞匀浆的情况下，只有13-OXO具有反应性。另外，仅含硫化合物半胱氨酸和谷胱甘肽显示出显着的反应速率。此外，用N-乙基马来酰亚胺处理结肠匀浆降低了[1-C-14] -13-OXO与细胞蛋白的结合。这些数据支持以下建议：13-HODE在与细胞蛋白结合之前需要通过脱氢成13-OXO进行代谢活化，并且蛋白质衍生的巯基参与结合反应。 [参考：27]

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