An Edaravone-Guided Design of a Rhodamine-Based Turn-on Fluorescent Probe for Detecting Hydroxyl Radicals in Living Systems,Analytical Chemistry

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An Edaravone-Guided Design of a Rhodamine-Based Turn-on Fluorescent Probe for Detecting Hydroxyl Radicals in Living Systems
Analytical Chemistry ( IF 6.7 ) Pub Date : 2021-10-13 , DOI: 10.1021/acs.analchem.1c03877
Liqin Chen ₁ , Xia Wu ₂ , Hanjie Yu ₃ , Lei Wu ₁ , Qin Wang ₄ , Jianjian Zhang ₁ , Xiaogang Liu ₂ , Zheng Li ₃ , Xiao-Feng Yang ₁

Affiliation

The hydroxyl radical (·OH), one of the reactive oxygen species (ROS) in biosystems, is found to be involved in many physiological and pathological processes. However, specifically detecting endogenous ·OH remains an outstanding challenge owing to the high reactivity and short lifetime of this radical. Herein, inspired by the scavenging mechanism of a neuroprotective drug edaravone toward ·OH, we developed a new ·OH-specific fluorescent probe RH-EDA. RH-EDA is a hybrid of rhodamine and edaravone and exploits a ·OH-specific 3-methyl-pyrazolone moiety to control its fluorescence behavior. RH-EDA itself is almost nonfluorescent in physiological conditions, which was attributed to the formation of a twisted intramolecular charge transfer (TICT) state upon photoexcitation and the acylation of its rhodamine nitrogen at the 3′ position. However, upon a treatment with ·OH, its edaravone subunit was converted to the corresponding 2-oxo-3-(phenylhydrazono)-butanoic acid (OPB) derivative (to afford RH-OPB), thus leading to a significant fluorescence increase (ca. 195-fold). RH-EDA shows a high sensitivity and selectivity to ·OH without interference from other ROS. RH-EDA has been utilized for imaging endogenous ·OH production in living cells and zebrafishes under different stimuli. Moreover, RH-EDA allows a high-contrast discrimination of cancer cells from normal ones by monitoring their different ·OH levels upon stimulation with β-Lapachone (β-Lap), an effective ROS-generating anticancer therapeutic agent. The present study provides a promising methodology for the construction of probes through a drug-guided approach.

中文翻译：

用于检测生命系统中羟基自由基的基于罗丹明的开启荧光探针的依达拉奉引导设计

羟基自由基（·OH）是生物系统中的活性氧（ROS）之一，被发现参与许多生理和病理过程。然而，由于该自由基的高反应性和短寿命，特异性检测内源性·OH仍然是一个突出的挑战。在此，受神经保护药物依达拉奉对·OH的清除机制的启发，我们开发了一种新的·OH特异性荧光探针RH-EDA。RH-EDA是罗丹明和依达拉奉的混合物，利用·OH 特异性 3-甲基-吡唑啉酮部分来控制其荧光行为。RH-EDA本身在生理条件下几乎不发荧光，这归因于在光激发时形成扭曲的分子内电荷转移 (TICT) 状态以及其 3' 位置的罗丹明氮酰化。然而，在用·OH处理后，其依达拉奉亚基转化为相应的2-氧代-3-(苯肼基)-丁酸(OPB)衍生物(得到RH-OPB )，从而导致荧光显着增加(ca . 195 倍）。RH-EDA显示出对·OH 的高灵敏度和选择性，而不受其他 ROS 的干扰。RH-EDA已被用于成像不同刺激下活细胞和斑马鱼的内源性·OH 产生。此外，RH-EDA通过在 β-Lapachone (β-Lap)（一种有效的产生 ROS 的抗癌治疗剂）刺激下监测癌细胞的不同·OH 水平，允许以高对比度区分癌细胞和正常细胞。本研究为通过药物引导的方法构建探针提供了一种有前途的方法。

更新日期：2021-10-26

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