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Phosphorogenic sensors for biothiols derived from cyclometalated iridium(III) polypyridine complexes containing a dinitrophenyl ether moiety
Journal of Inorganic Biochemistry ( IF 3.9 ) Pub Date : 2017-09-12 , DOI: 10.1016/j.jinorgbio.2017.08.037
Karson Ka-Shun Tso , Hua-Wei Liu , Kenneth Kam-Wing Lo

We report the synthesis and characterization of three cyclometalated iridium(III) polypyridine complexes containing a 2,4-dinitrophenyl ether moiety [Ir(pq)2(N^N)](PF6) (Hpq = 2-phenylquinoline; N^N = 4-(N-(4-(2,4-dinitrophenoxy)benzyloxy)carbonyl)aminomethyl-4′-methyl-2,2′-bipyridine (bpy-dinitro-1) (1a), 4-(2,4-dinitrophenoxy)methyl-4′-methyl-2,2′-bipyridine (bpy-dinitro-2) (2a), 4-(4-(2,4-dinitrophenoxy)phenyl)-2,2′-bipyridine (bpy-dinitro-3) (3a)) as intracellular sensors for biothiols. Due to the quenching effect of the dinitroaromatic moiety, these complexes were extremely weakly emissive. Upon the reaction with biothiols, however, the emission was turned on as a consequence of the departure of the quenching unit. The results from a range of experiments demonstrated that complex 1a was noncytotoxic under the conditions used for confocal imaging, showed facile cellular uptake, and can serve as a phosphorogenic intracellular sensor for biothiols including glutathione (GSH) and hydrogen sulfide.



中文翻译:

衍生自含二硝基苯基醚部分的环金属化铱(III)聚吡啶配合物的生物硫醇的生磷传感器

我们报告了合成和表征的三个环金属化铱(III)聚吡啶配合物,含有2,4-二硝基苯基醚部分[Ir(pq)2(N ^ N)](PF 6)(Hpq = 2-苯基喹啉; N ^ N = 4-(N-(4-(2,4-二硝基苯氧基)苄氧基)羰基)氨基甲基-4'-甲基-2,2'-联吡啶(bpy-dinitro-1)(1a),4-(2,4 -二硝基苯氧基)甲基-4'-甲基-2,2'-联吡啶(bpy-dinitro-2)(2a),4-(4-(2,4-二硝基苯氧基)苯基)-2,2'-联吡啶(bpy -二硝基-3)(3a))作为生物硫醇的细胞内传感器。由于二硝基芳族部分的猝灭作用,这些配合物极弱地发射。然而,在与生物硫醇反应时,由于淬灭单元的离开而打开了发射。一系列实验的结果表明,复合物1a在用于共聚焦成像的条件下是无细胞毒性的,显示出容易的细胞摄取,并且可以用作生物硫醇(包括谷胱甘肽(GSH)和硫化氢)的生磷细胞内传感器。

更新日期:2017-09-12
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