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A fluorescent probe for carbon monoxide based on allyl ether rather than allyl ester: A practical strategy to avoid the interference of esterase in cell imaging

Fang, Wen-Le, Tang, Ying-Jie, Guo, Xiao-Feng, Wang, Hong
Talanta 2019 v.205 pp. 120070
carbon monoxide, cell culture, detection limit, enzyme activity, esterases, esters, fetal bovine serum, fluorescence, fluorescent dyes, hydrolysis, image analysis, moieties, palladium, wavelengths
Pd0-mediated Tsuji-Trost reaction is a practical strategy to design fluorescent probes for carbon monoxide (CO) sensing, and in such reaction CO can reduce Pd2+ to Pd0 in-situ and remove allyl groups on fluorophores. In most of these probes, esters are commonly used to link allyl on fluorophores. We found that the ester groups could be hydrolyzed by esterase activity of fetal bovine serum (FBS), while FBS is a requisite in cell culture, and the hydrolysis could interfere the Pd0-mediated Tsuji-Trost reaction. In this study, we synthesized a fluorescent probe (Cou-CO) using allyl ether as reaction site rather than allyl ester. Cou-CO is non-fluorescence, and could react with CO under the presence of Pd0 to form Cou with strong fluorescence, and the maximum excitation and emission wavelengths of Cou are 464 nm and 495 nm respectively. Cou-CO shows excellent selectivity to CO and could avoid the effect of FBS with the limit of detection for CO is 78 nm. Finally, Cou-CO was successfully applied for imaging of CO in living cells.