Cucurbit[7]uril confined phenothiazine bridged bis(bromophenyl pyridine) activated NIR luminescence for lysosome imaging

• Published in: Chinese chemical letters Vol. 35; no. 6; p. 109183
• Main Authors: Wang, Hui-Juan, Xing, Wen-Wen, Yu, Zhen-Hai, Li, Yong-Xue, Zhang, Heng-Yi, Yu, Qilin, Zhu, Hongjie, Wang, Yao-Yao, Liu, Yu
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.06.2024
• Subjects: HClO/ClO; Macrocycle confined; Phenothiazine; Probe; Supramolecular assembly; HClO/ClO; Probe; Supramolecular assembly; Macrocycle confined; Phenothiazine
• DOI: 10.1016/j.cclet.2023.109183
• ISSN: 1001-8417

Macrocycle confinement induced guest near-infrared (NIR) luminescence was research hotspot currently. Here in, we reported a cucurbit[7]uril (CB[7]) confined 3,7-bis((E)-2-(pyridin-4-yl)vinyl)-10-H-phenothiazine bridged bis(4-(4-bromophenyl)pyridine) (G), which not only boosted its NIR luminescence but also realized detection of HClO/ClO− in living cells and lysosome imaging. Fluorescence spectroscopy experiments were performed to calculate the detection ability of probe G to HClO/ClO− up to 147 nmol/L. As compared with G, supramolecular probe G⊂CB[7] formed after encapsulated by CB[7], the detection ability towards HClO/ClO− was improved to 24 nmol/L which was ascribe to the macrocycle CB[7] confinement increasing the fluorescence intensity to 103 folds. Accompanying the excitation wavelength changing, the fluorescence red-shifted to 820 nm when excited by 570 nm light, which was used to NIR lysosome imaging. Meanwhile, the supramolecular assembly G⊂CB[7] was also successfully used to highly sense to exogenous HClO/ClO− in RAW 264.7 cells and live animal. The formed supramolecular assembly between phenothiazine derivative (G) and cucurbit[7]uril (CB[7]) not only boosted NIR fluorescence through macrocycle confinement, but also used to detect HClO/ClO−in vitro and in vivo with the sensitivity reached to 24 nmol/L and NIR lysosome cell imaging. [Display omitted]