8-(4-aminophenyl) BODIPYs as fluorescent pH probes: facile synthesis, computational study and lysosome imaging
8-(4-aminophenyl) BODIPYs as fluorescent pH probes: facile synthesis, computational study and lysosome imaging
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8-(4-氨基苯基) BODIPY 作为荧光 pH 探针：简便合成、计算研究和溶酶体成像
DOI：
10.1002/slct.201500016
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发表时间：
2016
期刊：
影响因子：
2.1
通讯作者：
Xing Guo-wen
中科院分区：
文献类型：
--
作者：
Zhang Yuan;Fang Hong-mei;Zhang Xiao-tai;Wang Shu;Xing Guo-wen
采用abuchwald - Hartwig交叉偶联反应合成了5种新型BODIPY基染料（3 a - e）。8‐（4‐氨基苯基）BODIPYs可作为荧光pH探针，具有宽响应范围。在中性或弱酸性条件下观察到3a - e的荧光强度较低，而随着pH值的进一步降低，荧光信号显著增加，表明它们对酸性pH变化高度敏感。探针对pH的荧光响应机制基于光诱导电子转移（PET），并通过密度泛函理论（DFT）和时间依赖密度泛函理论（TD - DFT）计算进行了研究。细胞成像实验证明3b （pKa 3.59）是一种新型的溶酶体靶向探针，具有优异的膜通透性、高灵敏度和选择性以及低细胞毒性。此外，pKa为2.66、2.51的探针3和探针3可能用于检测细菌中的极酸性条件。
Five novel BODIPY‐based dyes (3 a‐e) were facilely synthesizedviaBuchwald‐Hartwig cross coupling reaction. The 8‐(4‐aminophenyl)BODIPYs can be used as fluorescent pH probes with broad response ranges. Low fluorescence intensities of3a–ewere observed under neutral or weak acidic conditions, whereas, the fluorescence signals significantly increased with further decreasing pH values, indicating that they are highly sensitive to acidic pH alterations. Fluorescence response mechanism of the probes to pH is based on the photo‐induced electron transfer (PET), which was investigated by density functional theory (DFT) and time dependent‐density functional theory (TD‐DFT) calculations. Cell imaging experiments demonstrated3 b(pKa 3.59) was a novel lysosome‐targeting probe with excellent membrane permeability, high sensitivity and selectivity, as well as low cytotoxicity. In addition, probes3 aand3 dwith pKa 2.66, 2.51 could be potential for detecting extremely acidic conditions in bacteria.