Quinoline-derived fluorescent probes for the discrimination of Cys from Hcys/GSH and bioimaging in living cells.
Quinoline-derived fluorescent probes for the discrimination of Cys from Hcys/GSH and bioimaging in living cells.
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喹啉衍生的荧光探针，用于区分 Cys 与 Hcys/GSH 以及活细胞中的生物成像。
DOI：
10.1016/j.talanta.2018.04.044
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发表时间：
2018-08
期刊：
影响因子：
6.1
通讯作者：
Stadler Florian J
中科院分区：
文献类型：
--
作者：
Wu Qingqing;Mao Mao;Liang Wenlang;Stadler Florian J
开发对不同巯基化合物具有选择性的巯基特异性荧光探针比那些没有这种能力的荧光探针更具有实际意义。本工作合成了一种新的喹啉衍生荧光团，羟基取代喹啉-苯并[d]恶唑6，并与丙烯酸酯化得到两种荧光探针，BQA-1和BQA-2在pH7.4的水溶液中对半胱氨酸有很大的荧光响应，发射峰很大。从383 nm到518 nm的位移，超过130 nm。检测限低至0.59 μM。与BQA-1相比，BQA-2的丙烯酸酯部分进一步被吡啶基团修饰，其对Cys显示出开启荧光响应，检测限为0.98 μM。BQA-1和BQA-2对另外两种生物硫醇Hcys和GSH的反应较弱，对其他亲核试剂几乎没有反应。此外，通过细胞成像实验，证明了其在活细胞中检测生物硫醇的潜在应用。
Development of thiol-specific fluorescent probes with selectivity in different thiol compounds is more practical and significant than those without that capacity. In this work, a new quinoline-derived fluorophore, hydroxyl-substituted quinoline-benzo[d]oxazole6with high fluorescence quantum yield is synthesized and esterified with acrylic acid to afford two fluorescent probes,BQA-1andBQA-2for selectively discriminating Cys from Hcys/GSH based on conjugate addition-cyclization mechanism.BQA-1exhibits a large ratiometric fluorescence response toward Cys in aqueous pH 7.4 solution with big emission peak-shifting from 383 nm to 518 nm, over 130 nm. The detection limit is determined to be as low as 0.59 μM. In contrast toBQA-1,BQA-2whose acrylic ester moiety is further modified with pyridine group, displays a turn-on fluorescence response to Cys with detection limit of 0.98 μM. BothBQA-1andBQA-2have relatively weak response to another two biothiols, Hcys and GSH and nearly no response to other nucleophiles. Furthermore, the potential application for the detection of biothiols in living cells has been demonstrated by cell imaging experiment.
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