Analyte Regeneration Fluorescent Probes for Formaldehyde Enabled by Regiospecific Formaldehyde-induced Intramolecularity,Journal of the American Chemical Society

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Analyte Regeneration Fluorescent Probes for Formaldehyde Enabled by Regiospecific Formaldehyde-induced Intramolecularity
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-11-20 , DOI: 10.1021/jacs.8b09794
Hang Xu ₁ , Huan Xu ₁ , Shengnan Ma ₁ , Xiani Chen ₁ , Lixian Huang ₁ , Junwei Chen ₁ , Feng Gao ₁ , Rui Wang ₁ , Kaiyan Lou ₁ , Wei Wang _{1,

2}

Affiliation

An important challenge for reaction-based fluorescent probes is that they generally require analyte consumption for fluorescence signal generation, thus creating potential perturbation of native analyte homeostasis or change of local concentrations. Herein, we reported two formaldehyde (FA) regeneration fluorescent probes, NAP-FAP-1 and NAP-FAP-2. An unprecedented regiospecific FA-induced intramolecularity strategy is implemented in the probe design, which adopts 3-(benzylamino)-succinimide as the FA-selective reaction group. The probes are able to capture the analyte molecule, induce regiospecific imide bond cleavage, and then release the captured FA molecule with simultaneous fluorescence turn-on response via a unique dual PeT/ICT quenching mechanism. The probes have shown potentials in detection, comparison, and imaging of FA levels intracellularly and inside lysosomes. These features make them useful for the study of FA homeostasis and functions in biological systems with minimal perturbation.

中文翻译：

由区域特异性甲醛诱导的分子内作用实现的甲醛分析物再生荧光探针

基于反应的荧光探针的一个重要挑战是它们通常需要消耗分析物来产生荧光信号，从而对天然分析物稳态产生潜在的扰动或局部浓度的变化。在此，我们报道了两种甲醛 (FA) 再生荧光探针，NAP-FAP-1 和 NAP-FAP-2。在探针设计中实施了前所未有的区域特异性 FA 诱导的分子内策略，该策略采用 3-(苄基氨基)-琥珀酰亚胺作为 FA 选择性反应基团。探针能够捕获分析物分子，诱导区域特异性酰亚胺键裂解，然后通过独特的双 PeT/ICT 淬灭机制释放捕获的 FA 分子，同时荧光开启响应。这些探针在检测、比较、细胞内和溶酶体内部 FA 水平的成像。这些特征使它们可用于研究 FA 稳态和生物系统中具有最小扰动的功能。

更新日期：2018-11-20

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