Mitochondrial-Targeted AIE-Active Fluorescent Probe Based on Tetraphenylethylene Fluorophore with Dual Positive Charge Recognition Sites for Monitoring ATP in Cells,Analytical Chemistry

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Mitochondrial-Targeted AIE-Active Fluorescent Probe Based on Tetraphenylethylene Fluorophore with Dual Positive Charge Recognition Sites for Monitoring ATP in Cells
Analytical Chemistry ( IF 6.7 ) Pub Date : 2023-03-10 , DOI: 10.1021/acs.analchem.2c05523
Bin Yang ₁ , Ruowei Tian ₁ , Taiyu Guo ₁ , Wangbo Qu ₁ , Jiao Lu ₁ , Yong Li ₁ , Zhou Wu ₁ , Shihai Yan ₁ , Zhirong Geng ₂ , Zhilin Wang ₁

Affiliation

Adenosine triphosphate (ATP), as an important intracellular energy currency produced in mitochondria, is closely related to various diseases in living organisms. Currently, the biological application of AIE fluorophore as a fluorescent probe for ATP detection in mitochondria is rarely reported. Herein, D−π–A and D–A structure-based tetraphenylethylene (TPE) fluorophores were employed to synthesize six different ATP probes (P1–P6), and the phenylboronic acid groups and dual positive charge sites of probes could interact with the vicinal diol of ribose and negatively charged triphosphate structure of ATP, respectively. However, P1 and P4 with a boronic acid group and a positive charge site had poor selectivity for ATP detection. In contrast, P2, P3, P5, and P6 with dual positive charge sites exhibited better selectivity than P1 and P4. In particular, P2 had more advantages of high sensitivity, selectivity, and good time stability for ATP detection than P3, P5, and P6, which was ascribed to its D−π–A structure, linker 1 (1,4-bis(bromomethyl)benzene), and dual positive charge recognition sites. Then, P2 was employed to detect ATP, and it exhibited a low detection limit of 3.62 μM. Moreover, P2 showed utility in the monitoring of mitochondrial ATP level fluctuations.

中文翻译：

基于四苯乙烯荧光团的线粒体靶向 AIE 活性荧光探针，具有双正电荷识别位点，用于监测细胞中的 ATP

三磷酸腺苷（ATP）作为线粒体产生的重要细胞内能量货币，与生物体的各种疾病密切相关。目前，很少报道AIE荧光团作为荧光探针在线粒体中检测ATP的生物学应用。在此，采用基于 D-π-A 和 D-A 结构的四苯乙烯 (TPE) 荧光团合成六种不同的 ATP 探针 (P1-P6)，探针的苯基硼酸基团和双正电荷位点可以与邻位相互作用分别是核糖的二醇和 ATP 的带负电的三磷酸结构。然而，具有硼酸基团和正电荷位点的 P1 和 P4 对 ATP 检测的选择性较差。相比之下，具有双正电荷位点的 P2、P3、P5 和 P6 表现出比 P1 和 P4 更好的选择性。尤其，与P3、P5、P6相比，P2具有灵敏度高、选择性好、时间稳定性好等ATP检测优势，这主要归功于其D-π-A结构，接头1（1,4-双（溴甲基）苯）和双正电荷识别位点。然后，使用 P2 检测 ATP，检测限低至 3.62 μM。此外，P2 在监测线粒体 ATP 水平波动方面表现出实用性。

更新日期：2023-03-10

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