Department of Chemistry & Centre of Advanced Studies in Chemistry, Panjab University, Sector-14, Chandigarh, 160 014, India.
Rudolf Virchow Zentrum, Centre for Integrative and Translational Bioimaging, Julius-Maximillian, University of Wurzburg, 97080, Wurzburg, Germany.
Chembiochem. 2024 Feb 16;25(4):e202400074. doi: 10.1002/cbic.202400074. Epub 2024 Feb 1.
The synthesis of diarylamine-based organoselenium compounds via the nucleophilic substitution reactions has been described. Symmetrical monoselenides and diselenides were conveniently synthesized by the reduction of their corresponding selenocyanates using sodium borohydride. Selenocyanates were obtained from 2-chloro acetamides by the nucleophilic displacement with potassium selenocyanate. Selenides were synthesized by treating the 2-chloro acetamides with in situ generated sodium butyl selenolate as nucleophile. Further, the newly synthesized organoselenium compounds were evaluated for their glutathione peroxidase (GPx)-like activity in thiophenol assay. This study revealed that the methoxy-substituted organoselenium compounds showed significant effect on the GPx-like activity. The catalytic parameters for the most efficient catalysts were also determined. The anti-ferroptotic activity for all GPx-mimics evaluated in a 4-OH-tamoxifen (TAM) inducible GPx4 knockout cell line using liproxstatin as standard.
本文描述了通过亲核取代反应合成二芳基胺基有机硒化合物。通过使用硼氢化钠还原相应的硒氰酸盐，方便地合成了对称的单硒化物和二硒化物。硒氰酸盐是通过 2-氯乙酰胺与硒氰酸钾的亲核取代反应得到的。通过用原位生成的丁基硒醇钠作为亲核试剂处理 2-氯乙酰胺，合成了硒化物。此外，还通过噻吩酚测定法评估了新合成的有机硒化合物的谷胱甘肽过氧化物酶 (GPx) 样活性。该研究表明，甲氧基取代的有机硒化合物对 GPx 样活性有显著影响。还确定了最有效的催化剂的催化参数。使用 liproxstatin 作为标准，在 4-OH-他莫昔芬 (TAM) 诱导的 GPx4 敲除细胞系中，对所有评估的 GPx 模拟物的抗铁死亡活性进行了评估。
