Majumdar Anupam, Mondal Subhendu, Daniliuc Constantin G, Sahu Debashis, Ganguly Bishwajit, Ghosh Sourav, Ghosh Utpal, Ghosh Kumaresh
Department of Chemistry, University of Kalyani , Kalyani 741235, India.
Organisch-Chemisches Institut, Universität Münster , Corrensstrasse 40, 48159 Münster, Germany.
Inorg Chem. 2017 Aug 7;56(15):8889-8899. doi: 10.1021/acs.inorgchem.7b00835. Epub 2017 Jul 24.
α-Amino acid derived benzimidazole-linked rhodamines have been synthesized, and their metal ion sensing properties have been evaluated. Experimentally, l-valine- and l-phenylglycine-derived benzimidazole-based rhodamines 1 and 2 selectively recognize Al ion in aqueous CHCN (CHCN/HO 4/1 v/v, 10 mM tris HCl buffer, pH 7.0) over the other cations by exhibiting color and "turn-on" emission changes. In contrast, glycine-derived benzimidazole 3 remains silent in the recognition event and emphasizes the role of α-substitution of amino acid undertaken in the design. The fact has been addressed on the basis of the single-crystal X-ray structures and theoretical calculations. Moreover, pink 1·Al and 2·Al ensembles selectively sensed F ions over other halides through a discharge of color. Importantly, compounds 1 and 2 are cell permeable and have been used as imaging reagents for the detection of Al uptake in human lung carcinoma cell line A549.
已合成了α-氨基酸衍生的苯并咪唑连接的罗丹明，并评估了它们对金属离子的传感特性。实验表明，在水/乙腈（乙腈/水 4/1 v/v，10 mM 三羟甲基氨基甲烷盐酸盐缓冲液，pH 7.0）中，L-缬氨酸和L-苯甘氨酸衍生的基于苯并咪唑的罗丹明1和2通过颜色变化和“开启”发射变化，比其他阳离子更能选择性地识别铝离子。相比之下，甘氨酸衍生的苯并咪唑3在识别过程中没有反应，这突出了设计中氨基酸α-取代的作用。这一事实已通过单晶X射线结构和理论计算得到证实。此外，粉红色的1·Al和2·Al组合通过颜色变化比其他卤化物更能选择性地检测氟离子。重要的是，化合物1和2具有细胞渗透性，并已用作成像试剂，用于检测人肺癌细胞系A549中铝的摄取情况。
