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基于尼罗红骨架的可视化多硫化氢荧光探针的苯磺酰类似物的分子工程

Molecular engineering of benzenesulfonyl analogs for visual hydrogen polysulfide fluorescent probes based on Nile red skeleton.

作者信息

Feng Qian, Song Yiming, Ma Yixuan, Deng Yan, Xu Pengyue, Sheng Kangjia, Zhang Yongmin, Li Jianli, Wu Shaoping

机构信息

Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, Biomedicine Key Laboratory of Shaanxi Province, Northwest University, Xi'an 710069, PR China.

School of Chemical Engineering, Northwest University, 229 Taibai Road, Xi'an, Shaanxi 710069, PR China.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2023 Aug 5;296:122658. doi: 10.1016/j.saa.2023.122658. Epub 2023 Mar 21.

DOI:10.1016/j.saa.2023.122658
PMID:36989690
Abstract

Hydrogen polysulfide (HS, n > 1) has a valuable function in various aspects of biological regulation. Therefore, it is of great significance to realize the visual monitoring of HS levels in vivo. Herein, a series of fluorescent probes NR-BS were constructed by changing types and positions of substituents on the benzene ring of benzenesulfonyl. Among them, probe NR-BS4 was optimized due to its wide linear range (0 ∼ 350 μM) and little interference from biothiols. In addition, NR-BS4 has a broad pH tolerance range (pH = 4 ∼ 10) and high sensitivity (0.140 μM). In addition, the PET mechanism of probe NR-BS4 and HS was demonstrated by DFT calculations and LC-MS. The intracellular imaging studies indicate that NR-BS4 can be successfully devoted to monitor the levels of exogenous and endogenous HS in vivo.

摘要

多硫化氢(HS,n>1)在生物调节的各个方面都具有重要作用。因此,实现体内HS水平的可视化监测具有重要意义。在此,通过改变苯磺酰基苯环上取代基的类型和位置,构建了一系列荧光探针NR-BS。其中,探针NR-BS4因其较宽的线性范围(0∼350μM)和来自生物硫醇的干扰较小而得到优化。此外,NR-BS4具有较宽的pH耐受范围(pH=4∼10)和高灵敏度(0.140μM)。此外,通过密度泛函理论(DFT)计算和液相色谱-质谱联用(LC-MS)证实了探针NR-BS4与HS的PET机制。细胞内成像研究表明,NR-BS4能够成功用于监测体内外源性和内源性HS的水平。

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