Fluorescent probes based on nucleophilic aromatic substitution reactions for reactive sulfur and selenium species: Recent progress, applications, and design strategies

Yuning Liu; Yanan Yu; Qingyu Zhao; Chaohua Tang; Huiyan Zhang; Yuchang Qin; Xiaohui Feng; Junmin Zhang

doi:10.1016/j.ccr.2020.213601

Fluorescent probes based on nucleophilic aromatic substitution reactions for reactive sulfur and selenium species: Recent progress, applications, and design strategies

Coord Chem Rev. 2021 Jan 15:427:213601. doi: 10.1016/j.ccr.2020.213601. Epub 2020 Oct 2.

Authors

Yuning Liu^{1

2}, Yanan Yu^{1

2}, Qingyu Zhao^{1

2}, Chaohua Tang^{1

2}, Huiyan Zhang^{1

2}, Yuchang Qin^{1

2}, Xiaohui Feng^{1

2}, Junmin Zhang^{1

2}

Affiliations

¹ State Key Laboratory of Animal Nutrition, Institute of Animal Science, Chinese Academy of Agricultural Sciences, Beijing 100193, China.
² Scientific Observing and Experiment Station of Animal Genetic Resources and Nutrition in North China of Ministry of Agriculture and Rural Affairs, Institute of Animal Science, Chinese Academy of Agricultural Sciences, Beijing 100193, China.

Abstract

Reactive sulfur species (RSS) and reactive selenium species (RSeS) are important substances for the maintenance of physiological balance. Imbalance of RSS and RSeS is closely related to a series of human diseases, so it is considered to be an important biomarker in early diagnosis, treatment, and stage monitoring. Fast and accurate quantitative analysis of different RSS and RSeS in complex biological systems may promote the development of personalized diagnosis and treatment in the future. One way to explore the physiological function of various types of RSS and RSeS in vivo is to detect them at the molecular level, and one of the most effective methods for this is to use fluorescent probes. Nucleophilic aromatic substitution (S_NAr) reactions are commonly exploited as a detection mechanism for RSS and RSeS in fluorescent probes. In this review, we cover recent progress in fluorescent probes for RSS and RSeS based on S_NAr reactions, and discuss their response mechanisms, properties, and applications. Benzenesulfonate, phenyl-O ether, phenyl-S ether, phenyl-Se ether, 7-nitro-2,1,3-benzoxadiazole (NBD), benzoate, and selenium-nitrogen bonds are all good detection groups. Moreover, based on an integration of different reports, we propose the design and synthesis of RSS- and RSeS-selective probes based on S_NAr reactions, current challenges, and future research directions, considering the selection of active sites, the effect of substituents on the benzene ring, and the introduction of other functional groups.

Publication types

Review