Uncatalyzed Click Reaction between Phenyl Azides and Acrolein: 4-Formyl-1,2,3-Triazolines as “Clicked” Markers for Visualizations of Extracellular Acrolein Released from Oxidatively Stressed Cells

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• 作者：Ambara R. Pradipta ; Misako Taichi ; Ikuhiko Nakase ; Elena Saigitbatalova ; Almira Kurbangalieva ; Shinobu Kitazume ; Naoyuki Taniguchi ; Katsunori Tanaka
• 刊名：ACS Sensor
• 出版年：2016
• 出版时间：May 27, 2016
• 年：2016
• 卷：1
• 期：5
• 页码：623-632
• 全文大小：846K
• ISSN：2379-3694

文摘

Acrolein, a highly toxic α,β-unsaturated aldehyde, has been a longstanding key biomarker associated with a range of disorders related to oxidative stresses. Currently available analytical methods rely on the indirect protocols, e.g., derivatization/HPLC or mAb detection of the lysine adducts. Consequently, developing new analytical tools for acrolein detection that are straightforward, cost-effective, selective, and preferably feasible using live cells remains a highly essential pursuit in the diagnosis and therapeutic treatment of oxidative stress-related diseases. We demonstrated that for the first time aryl azides can rapidly and selectively react with acrolein in a “click” manner to provide 4-formyl-1,2,3-triazolines and 4-formyl-1,2,3-triazoles, which represents an unexplored reactivity of aryl azides. When treating a fluorescently labeled phenyl azide with oxidatively stressed or smoking-associated cell models, these heterocyclic compounds could be selectively taken up by the cells and preferably localized at the endoplasmic reticulum (ER) and lysosome, leading to a new tool for both effectively detecting acrolein level and directly imaging live cells that are under stress. The detection method developed here is convenient: target cells may be treated with fluorescently labeled azides to enable the direct and efficient detection of acrolein in live system. The simple stuctures of the azide probes allows for functional groups other than fluorescent groups to be readily linked to aryl azides to image, examine, or target cells associated with oxidative stress processes. We developed a new method for detecting and imaging acrolein extracellularly released by cells in the context of oxidative stress processes or introduced via environmental exposure.