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

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 × 107 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 µM) 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.

本研究报道了一种单步、高产率、高纯度、环保且可规模化的制备工艺，用于合成硒衍生物二乙基硒代二甘醇酸酯（diethyl selenodiglycolate）。二乙基硒代二甘醇酸酯可快速还原次氯酸（HOCl，二级速率常数为7×10^7 M⁻¹·s⁻¹），生成对应的硒氧化物。在活化的HL-60细胞中，二乙基硒代二甘醇酸酯仅与次氯酸发生选择性反应（半数抑制浓度IC50=23.07 μM），而不与超氧阴离子自由基或过氧化氢发生反应，且无任何细胞毒性。上述结果表明，这种合成简便的硒化物可高效且特异性地与有害促氧化剂次氯酸发生反应，是一种有望应用于氧化炎症相关病症的候选化合物。