Diethyl Selenodiglycolate: An Eco-Friendly Synthetic Antioxidant with Potential Application to Inflammatory Disorders

被引:4
作者
Pinatto-Botelho, Marcos F. [1 ,2 ]
da Silva, Railmara P. [3 ]
Archilha, Marcos V. L. R. [1 ,2 ]
Giroldo, Lilian [1 ]
Kuznetsov, Aleksey E. [4 ]
Meotti, Flavia C. [3 ]
dos Santos, Alcindo A. [1 ]
机构
[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, BR-05508000 Sao Paulo, SP, Brazil
[2] Univ Sao Paulo, SelenoLife, Ctr Inovacao Empreendedorismo & Tecnol CIETEC, IPEN, BR-05508000 Sao Paulo, SP, Brazil
[3] Univ Sao Paulo, Inst Quim, Dept Bioquim, BR-05508000 Sao Paulo, SP, Brazil
[4] Univ Tecn Federico Santa Maria, Dept Chem, Av Santa Maria 6400, Santiago 7660251, Chile
基金
巴西圣保罗研究基金会;
关键词
diethyl selenodiglycolate; antioxidant; inflammation; oxidative burst; hypochlorous acid; PEROXIDASE-LIKE ACTIVITY; HYPOCHLOROUS ACID; PROTEIN OXIDATION; SELENIUM; MYELOPEROXIDASE; ORGANOSELENIUM; EBSELEN; ANALOGS; SUPEROXIDE; MECHANISMS;
D O I
10.21577/0103-5053.20200009
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This study describes a single step. high yield and purity. ecofriendly and scalable procedure to prepare a selenium derivative (diethyl selenodiglycolate). Diethyl selenodiglycolate rapidly reduces hypochlorous acid (HOCl, second-order rate constant of 7 x 10(7) M-1 s(-1)) to generate its corresponding selenoxide. In activated HL-60 cells, diethyl selenodiglycolate selectively reacted with HOCl (half maximal inhibitory concentration (IC50) = 23.07 mu M) but not with superoxide anion radical or hydrogen peroxide without any cytotoxicity. These results show that this synthetically simple selenide reacts in a very efficient and specific way with the harmful pro-oxidant HOCl being a promising compound to be applied in oxidative inflammatory-related conditions.
引用
收藏
页码:1239 / 1248
页数:10
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