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题名: The Unexpected and Exceptionally Facile Chemical Modification of the Phenolic Hydroxyl Group of Tyrosine by Polyhalogenated Quinones under Physiological Conditions
作者: Qu, Na1, 2; Li, Feng1, 2; Shao, Bo1, 2; Shao, Jie1, 2; Zhai, Guijin3, 4; Wang, Fuyi3; Zhu, Ben-Zhan1, 2
刊名: CHEMICAL RESEARCH IN TOXICOLOGY
发表日期: 2016-10-01
卷: 29, 期:10, 页:1699-1705
收录类别: SCI
英文摘要: The phenolic hydroxyl group of tyrosine residue plays a crucial role in the structure and function of many proteins. However, little study has been reported about its modification by chemical agents under physiological conditions. In this study, we found, unexpectedly, that the phenolic hydroxyl group of tyrosine can be rapidly and efficiently modified by tetrafluoro-1,4-benzoquinone and other polyhalogenated quinones, which are the major genotoxic and carcinogenic quinoid metabolites of polyhalogenated aromatic compounds. The modification was found to be mainly due to the formation of a variety of fluoroquinone-O-tyrosine conjugates and their hydroxylated derivatives via nucleophilic substitution pathway. Analogous modifications were observed for tyrosine-containing peptides. Further studies showed that the blockade of the reactive phenolic hydroxyl group of tyrosine in the substrate peptide, even by very low concentration of tetrafluoro-1,4-benzoquinone, can prevent the kinase catalyzed tyrosine phosphorylation. This is the first report showing the exceptionally facile chemical modification of the phenolic hydroxyl group of tyrosine by polyhalogenated quinones under normal physiological conditions, which may have potential biological and toxicological implications.
语种: 英语
内容类型: 期刊论文
URI标识: http://ir.iccas.ac.cn/handle/121111/35485
Appears in Collections:活体分析化学实验室_期刊论文

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作者单位: 1.Chinese Acad Sci, Ecoenvironm Sci Res Ctr, State Key Lab Environm Chem & Ecotoxicol, 18 Shuangqin Rd, Beijing 100085, Peoples R China
2.Chinese Acad Sci, Univ Chinese Acad Sci, 18 Shuangqin Rd, Beijing 100085, Peoples R China
3.Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Analyt Chem Living Biosyst, Inst Chem, Beijing 100190, Peoples R China
4.Tianjin Med Univ, Tianjin Res Ctr Basic Med Sci, Tianjin 300070, Peoples R China
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