A flavone-based turn-on fluorescent probe for intracellular cysteine/homocysteine sensing with high selectivity

• Published in: Talanta (Oxford) 2016-01, Vol.146, p.41-48
• Main Authors: Zhang, Jian, Lv, Yanlin, Zhang, Wei, Ding, Hui, Liu, Rongji, Zhao, Yongsheng, Zhang, Guangjin, Tian, Zhiyuan
• Format: Article
• Language: English
• Subjects: Bioimaging; Chemistry Techniques, Analytical - instrumentation; Cyclization; Cysteine - analysis; Cysteine - chemistry; Cysteine/homocysteine; Electron Transport; Flavones - chemistry; Fluorescent Dyes - chemistry; Fluorescent probe; Homocysteine - analysis; Humans; Intracellular Space - chemistry; Light; MCF-7 Cells; Optical Imaging; Spectrometry, Fluorescence
• ISSN: 0039-9140; 1873-3573
• DOI: 10.1016/j.talanta.2015.08.025

A new type of flavone-based fluorescent probe (DMAF) capable of cysteine (Cys)/homocysteine (Hcy) sensing with high selectivity over other amino acids was developed. Such type of probe undergoes Cys/Hcy-mediated cyclization reaction with the involvement of its aldehyde group, which suppresses of the photoinduced electron transfer (PET) process of the probe molecule and consequently leads to the enhancement of fluorescence emission upon excitation using visible light. The formation of product of the Cys/Hcy-mediated cyclization reaction was confirmed and the preliminary fluorescence imaging experiments revealed the biocompatibility of the as-prepared probe and validated its practicability for intracellular Cys/Hcy sensing. A new type of flavone-based fluorescent probe (DMAF) capable of cysteine (Cys)/homocysteine (Hcy) sensing with high selectivity over other amino acids was developed. Such type of probe undergoes Cys/Hcy-mediated cyclization reaction with the involvement of its aldehyde group, which suppresses of the photoinduced electron transfer (PET) process of the probe molecule and consequently leads to the enhancement of fluorescence emission upon excitation using visible light. The formation of product of the Cys/Hcy-mediated cyclization reaction was confirmed and the preliminary fluorescence imaging experiments revealed the biocompatibility of the as-prepared probe and validated its practicability for intracellular Cys/Hcy sensing. [Display omitted] •Flavone-based highly selective fluorescent probe for Cys/Hcy sensing was developed.•The ability of the probe for micromolar level Cys/Hcy sensing was confirmed.•The practicability of the probe for intracellular Cys/Hcy sensing was validated.