Synthesis of Vitamin E-Carnosine (VECAR): New Antioxidant Molecule with Potential Application in Atherosclerosis
Synthesis of Vitamin E-Carnosine (VECAR): New Antioxidant Molecule with Potential Application in Atherosclerosis
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DOI：
10.1080/00397911.2011.632829
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发表时间：
2013-05-03
影响因子：
2.1
通讯作者：
Sabliov, Cristina
中科院分区：
文献类型：
--
作者：
Astete, Carlos E.;Meador, Danielle Songe;Sabliov, Cristina
天然抗氧化剂，如肌肽和-生育酚（维生素E）可以预防几种与氧化应激相关的疾病，如动脉粥样硬化和阿尔茨海默氏症。-生育酚和肌肽的合成可以利用-生育酚的细胞运输机制，通过-生育酚转移蛋白（-TTP）将-生育酚和肌肽定位在亲脂和亲水结构域的界面上，保护两者不被氧化。成功合成了一种新的-生育酚（维生素E）和肌肽异二聚体，VECAR共进行了九个步骤。VECAR设计使用一个13碳的植基链模拟物在C2碳位置连接肌肽和Trolox。这一设计特点预计将保持与-TTP的结合，同时保持两种异源二聚体成分的抗氧化活性。我们的研究结果证实，与-生育酚和Trolox相比，在体外DPPH试验中，VECAR的抗氧化活性没有下降。本文有补充材料。去出版商的在线版合成通信(R)查看免费补充。
Natural antioxidants such as carnosine and -tocopherol (vitamin E) provide protection against several oxidative stress-related diseases such as atherosclerosis and Alzheimer's. The synthetic combination of -tocopherol and carnosine can take advantage of the cellular transport mechanism of -tocopherol by -tocopherol transfer protein (-TTP) to colocate -tocopherol and carnosine at the interface between a lipophilic and a hydrophilic domain and protect both from oxidation. Successful synthesis of a novel heterodimer of -tocopherol (vitamin E) and carnosine, VECAR was carried out in a total of nine steps. The VECAR design uses a 13-carbon phytyl-chain mimic to link carnosine to Trolox at the C2 carbon position. This design feature is anticipated to maintain binding to -TTP, while maintaining the antioxidant activity of the two heterodimer components. Our results confirmed that there was no loss in antioxidant activity in VECAR using an in-vitro DPPH assay, versus -tocopherol and Trolox. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental.