• 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>Chemistry: A European journal >Pyridoxine-Derived Organoselenium Compounds with Glutathione Peroxidase-Like and Chain-Breaking Antioxidant Activity
【24h】

Pyridoxine-Derived Organoselenium Compounds with Glutathione Peroxidase-Like and Chain-Breaking Antioxidant Activity

机译：具有谷胱甘肽过氧化物酶和断链抗氧化活性的吡y醇衍生的有机硒化合物

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

One of the vitamin B6 vitamers, pyridoxine, was modified to incorporate selenium in various oxidation states in place of the methyl group in position 2. Such compounds were conveniently accessed by treatment of bis-4,5-(carboethoxy)-2-iodo-3-pyridinol with disodium diselenide and LiAlH4-reduction. After work-up, selone 7 was isolated in good yield as an air-stable crystalline material. Hydrogen bonding to the neighboring hydroxyl group, as revealed by the short intramolecular Se···H distance in the crystal structure is likely to provide extra stabilization to the compound. Computational studies showed that selone 7 is more stable than the corresponding selenol tautomer by 12.2 kcalmol~(-1). Hydrogen peroxide oxidation of the selone 7 afforded diselenide 12, and, on further oxidation, seleninic acid 13. Treatment of the seleninic acid with thiophenol provided an isolable selenosulfide 14. The glutathione peroxidase-like properties of the pyridoxine-derived compounds were assessed by using the coupled reductase method. Seleninic acid 13 was found to be twofold more active than ebselen. The chain-breaking capacity of the pyridoxine compounds were studied in a water/chlorobenzene membrane model containing linoleic acid as an oxidizable substrate and N-acetylcysteine as a thiol reducing agent. Diselenide 15 could match a-tocopherol when it comes to reactivity towards peroxyl radicals and inhibition time.
机译：对维生素B6维生素之一吡pyr醇进行了修饰，以取代处于2位甲基的各种氧化态的硒。通过处理bis-4,5-（carboethoxy）-2-iodo- 3-吡啶二硒代二钠和LiAlH4-还原。后处理后，以良好的产率分离出selone 7，其为空气稳定的晶体材料。如晶体结构中较短的分子内Se···H距离所示，氢与相邻羟基的键合可能为该化合物提供额外的稳定性。计算研究表明，selone 7比相应的硒酚互变异构体稳定12.2 kcalmol〜（-1）。 selone 7的过氧化氢氧化提供了二硒化物12，硒酸进一步氧化后得到硒酸13。用硫酚处理硒酸提供了可分离的硒硫化物14。吡using醇新衍生物的谷胱甘肽过氧化物酶样性质通过使用偶联还原酶法。发现硒酸13的活性是依布硒仑的两倍。在含有亚油酸作为可氧化底物和N-乙酰基半胱氨酸作为硫醇还原剂的水/氯苯膜模型中研究了吡ido醇化合物的断链能力。当涉及过氧自由基的反应性和抑制时间时，二硒化物15可以与α-生育酚匹配。

著录项

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号