生物正交化学
醛
荧光
化学选择性
荧光团
部分
生命系统
光化学
化学
组合化学
纳米技术
计算机科学
生物化学
材料科学
有机化学
催化作用
点击化学
物理
量子力学
人工智能
作者
Rachel Wills,Rajendra P. Shirke,Hannah R. Hrncir,John M. Talbott,Kirti Sad,Jennifer M. Spangle,Adam D. Gracz,Manoj C. Raj
出处
期刊:Chemical Science
[The Royal Society of Chemistry]
日期:2024-01-01
卷期号:15 (13): 4763-4769
摘要
Aldehydes, pervasive in various environments, pose health risks at elevated levels due to their collective toxic effects via shared mechanisms. Monitoring total aldehyde content in living systems is crucial due to their cumulative impact. Current methods for detecting cellular aldehydes are limited to UV and visible ranges, restricting their analysis in living systems. This study introduces an innovative reaction-based trigger that leverages the exceptional selectivity of 2-aminothiophenol for aldehydes, leading to the production of dihydrobenzothiazole and activating a fluorescence response. Using this trigger, we developed a series of fluorescent probes for aldehydes by altering the fluorophore allowing for excitation and emission wavelengths across the visible to near-infrared spectral regions without compromising the reactivity of the bioorthogonal moiety. These probes exhibit remarkable aldehyde chemoselectivity, rapid kinetics, and high quantum yields, enabling the detection of diverse aldehyde types, both exogenous and endogenous, within complex biological contexts. Notably, we employed the most red-shifted near-infrared probe from this series to detect aldehydes in living systems, including biliary organoids and mouse organs. These probes provide valuable tools for exploring the multifaceted roles of aldehydes in biological functions and diseases within living systems, laying the groundwork for further investigations.
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