The reaction of ebselen with peroxynitrite
The reaction of ebselen with peroxynitrite
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DOI：
10.1021/tx950115u
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发表时间：
1996-01-01
影响因子：
4.1
通讯作者：
Sies, H
中科院分区：
文献类型：
--
作者：
Masumoto, H;Sies, H
Ebselen，2-苯基-1，2-苯并异硒-3(2H)-酮与过氧亚硝酸根迅速反应，反应速率常数约为10(6)M(-1)S(-1)。该反应生成母体分子2-苯基-1，2-苯并异硒-3(2H)-酮-1-氧化物的氧化硒，其化学计量比为1摩尔ebselen反应和每摩尔过氧亚硝酸根生成的氧化硒。在中性和碱性条件下(pH 10~11)对反应进行了详细的研究。在以过亚硝酸(ONOOH)为主的酸性条件下，由于过亚硝酸(pK(A)=6.8)的迅速衰变，氧化亚硒的产率较低。减少细胞中的氧化硒以再生ebselen将允许对过氧亚硝酸根的持续防御。这种新的反应构成了一条潜在的细胞防线，对抗炎症过程中重要的反应物种之一的过氧亚硝酸盐。
Ebselen, 2-phenyl-1,2-benzisoselenazol-3(2H)-one rapidly reacts with peroxynitrite, the rate constant being of the order of 10(6) M(-1) s(-1) the reaction yields the selenoxide of the parent molecule, 2-phenyl-1,2-benzisoselenazol-3(2H)-one 1-oxide, as the sole selenium-containing product; a stoichiometry of 1 mol of ebselen reacted and of the selenoxide formed per mole of peroxynitrite was observed. The reaction was studied in detail at neutral and alkaline pH (pH 10-11). It also proceeds at acidic pH where peroxynitrous acid (ONOOH) is predominant, the yield of the selenoxide being lower because peroxynitrous acid (pK(a) = 6.8) decays rapidly. Reduction of the selenoxide in cells to regenerate ebselen would allow for a sustained defense against peroxynitrite. This novel reaction constitutes a potential cellular defense line against peroxynitrite, one of the important reactive species in inflammatory processes.