Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Kyoto 606-8522, Japan.
Bioorg Med Chem. 2011 Jul 15;19(14):4162-72. doi: 10.1016/j.bmc.2011.06.015. Epub 2011 Jun 13.
In this paper we report a disulfide formation of thiols induced by epolactaene and its derivatives. We previously reported the disulfide formation of N-acetylcysteine methyl ester by epolactaene in a 1:1 MeOH/0.5M NaHCO(3) aq solution. The present studies reveal that the disulfide formation proceeds under mild conditions such as in PBS at pH 7.3, suggesting that epolactaene may induce disulfide formation of cellular thiols. This compound induces the disulfide formation of several thiols in a 1:1 MeOH/0.5M NaHCO(3) aq solution at room temperature. Moreover, our results show that the acyl side-chain of epolactaene greatly influences the products of the reaction. We analyzed the reaction mechanism by using thiolysis products of epolactaene derivatives and propose a new reaction mechanism.
本文报道了表鬼臼毒素及其衍生物诱导硫醇二硫化物的形成。我们之前报道了表鬼臼毒素在 1:1 MeOH/0.5M NaHCO(3) aq 溶液中诱导 N-乙酰半胱氨酸甲酯形成二硫化物。本研究表明，在温和条件下，如 PBS 在 pH 7.3 下，二硫化物的形成会进行，提示表鬼臼毒素可能诱导细胞硫醇的二硫化物形成。该化合物在室温下在 1:1 MeOH/0.5M NaHCO(3) aq 溶液中诱导几种硫醇的二硫化物形成。此外，我们的结果表明表鬼臼毒素的酰基侧链对反应产物有很大影响。我们通过使用表鬼臼毒素衍生物的硫解产物来分析反应机制，并提出了一个新的反应机制。
