Key Laboratory of Natural Resources of Changbai Mountain & Functional Molecules of the Ministry of Education, Department of Chemistry, Yanbian University, Yanji 133002, PR China.
Key Laboratory of Natural Resources of Changbai Mountain & Functional Molecules of the Ministry of Education, Department of Chemistry, Yanbian University, Yanji 133002, PR China.
Anal Chim Acta. 2017 Nov 15;993:87-95. doi: 10.1016/j.aca.2017.09.028. Epub 2017 Sep 28.
A novel fluorescent probe 1 based on acridine orange was developed for the selective detection and bioimaging of biothiols. The probe exhibits higher selectivity and turn-on fluorescence response to cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) than to other amino acids. Importantly, the probe responds to GSH and Cys/Hcy with distinct fluorescence emissions in PBS buffer at pH of 7.4. The Cys/Hcy-triggered tandem SAr-rearrangement reaction and GSH-induced SAr reaction with the probe led to the corresponding amino-acridinium and thio-acridinium dyes, respectively, which can discriminate GSH from Cys/Hcy through different emission channels. Interestingly, Cys finishes the tandem reaction with the probe and subsequently forms amino-acridinium and Hcy/GSH induces SAr reaction with the probe to form thio-acridiniums at weakly acidic conditions (pH 6.0), enabling Cys to be discriminated from Hcy/GSH at different emissions. Finally, we demonstrated that probe 1 can selectively probe GSH over Cys and Hcy or Cys over GSH and Hcy in HeLa cells through multicolor imaging.
一种基于吖啶橙的新型荧光探针 1 被开发用于生物硫醇的选择性检测和生物成像。该探针对半胱氨酸 (Cys)、同型半胱氨酸 (Hcy) 和谷胱甘肽 (GSH) 的选择性和开启荧光响应高于其他氨基酸。重要的是，探针在 pH 值为 7.4 的 PBS 缓冲液中对 GSH 和 Cys/Hcy 具有不同的荧光发射。Cys/Hcy 触发的串联 SAr 重排反应和 GSH 诱导的探针 SAr 反应分别导致相应的氨基吖啶和硫代吖啶染料，它们可以通过不同的发射通道区分 GSH 与 Cys/Hcy。有趣的是，Cys 与探针完成串联反应，随后在弱酸性条件 (pH 6.0) 下形成氨基吖啶，而 Hcy/GSH 与探针诱导 SAr 反应形成硫代吖啶，使 Cys 能够在不同的发射中与 Hcy/GSH 区分开来。最后，我们通过多色成像证明探针 1 可以选择性地在 HeLa 细胞中探测 GSH 与 Cys 和 Hcy 或 Cys 与 GSH 和 Hcy。
