N-Positive ion activated rapid addition and mitochondrial targeting ratiometric fluorescent probes for in vivo cell H₂S imaging

Abstract

Heterocyclic compound quinoline and its derivatives exist in natural compounds and have a broad spectrum of biological activity. They play an important role in the design of new structural entities for medical applications. Similarly, indoles and their derivatives are found widely in nature. Amino acids, alkaloids and auxin are all derivatives of indoles, as are dyes, and their condensation with aldehydes makes it easy to construct reaction sites for nucleophilic addition agents. In this work, we combine these two groups organically to construct a rapid response site (within 30 s) for H₂S, and at the same time, a ratiometric fluorescence response is presented throughout the process of H₂S detection. As such, the lower detection limit can reach 55.7 nmol/L for H₂S. In addition, cell imaging shows that this probe can be used for the mitochondrial targeted detection of endogenous and exogenous H₂S. Finally, this probe application was verified by imaging H₂S in nude mice.

Graphical abstract

Keywords

heterocyclic compound / hydrogen sulfide / ratiometric / mitochondrial targeted

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Acknowledgments

We thank the National Natural Science Foundation of China (Grant Nos. 21775096 and 21878180), One hundred people plan of Shanxi Province, Shanxi Province “1331 project” key innovation team construction plan cultivation team (No. 2018-CT-1), 2018 Xiangyuan County Solid Waste Comprehensive Utilization Science and Technology Project (No. 2018XYSDJS-05), Key R&D Program of Shanxi Province (No. 201903D421069), the Shanxi Province Science Foundation (No. 201901D111015), Shanxi Collaborative Innovation Center of High Value-added Utilization of Coal-related Wastes (No. 2015-10-B3), the Shanxi Province Foundation for Selected Returnee (No. 2019), Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi (No. 2019L0031), Project of Graduate Innovation of Shanxi Province (No. 2020), Key R&D and transformation plan of Qinghai Province (No. 2020-GX-101) and Scientific Instrument Center of Shanxi University (No. 201512).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at http://dx.doi.org/10.1007/s11705-021-2048-8 and is accessible for authorized users.

Compliance with Ethics Guidelines

Yan Shi, Fangjun Huo, Yongkang Yue and Caixia Yin declare that they have no conflict of interest. All institutional and national guidelines for the care and use of laboratory animals were followed.

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