Abstract

Near-infrared (NIR) fluorescent probes are attractive tools for bioimaging applications because of their low auto-fluorescence interference, minimal damage to living samples, and deep tissue penetration. H2S is a gaseous signaling molecule that is involved in redox homeostasis and numerous biological processes in vivo. To this end, we have developed a new red shifted fluorescent probe 1 to detect physiological H2S in live cells. The probe 1 is based on a rhodamine derivative as the red shifted fluorophore and the thiolysis of 7-nitro 1,2,3-benzoxadiazole (NBD) amine as the H2S receptor. The probe 1 displays fast fluorescent enhancement at 660 nm (about 10-fold turn-ons, k2 = 29.8 M−1s−1) after reacting with H2S in buffer (pH 7.4), and the fluorescence quantum yield of the activated red shifted product can reach 0.29. The probe 1 also exhibits high selectivity and sensitivity towards H2S. Moreover, 1 is cell-membrane-permeable and mitochondria-targeting, and can be used for imaging of endogenous H2S in living cells. We believe that this red shifted fluorescent probe can be a useful tool for studies of H2S biology.

Highlights

  • Biological reports have demonstrated the important role of H2 S, and the results suggested that endogenously-produced hydrogen sulfide (H2 S) has been marked as gasotransmitter, allowing the regulation of numerous important physiological functions including; cardiovascular, gastrointestinal, endocrine, nervous, and immune systems [1,2,3]

  • The interest in the molecular mechanisms of H2 S associated with physiology and pathology was sparked out of its recognition as a vital signaling molecule

  • In tumor biology, it is proposed that the both production and inhibition of H2 S concentration beyond a Molecules 2020, 25, 437; doi:10.3390/molecules25030437

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Summary

Introduction

Biological reports have demonstrated the important role of H2 S, and the results suggested that endogenously-produced hydrogen sulfide (H2 S) has been marked as gasotransmitter, allowing the regulation of numerous important physiological functions including; cardiovascular, gastrointestinal, endocrine, nervous, and immune systems [1,2,3]. As an important role played by H2 S in tumor biology, it is proposed that the both production and inhibition of H2 S concentration beyond a Molecules 2020, 25, 437; doi:10.3390/molecules25030437 www.mdpi.com/journal/molecules important role played by H2S in tumor biology, it is proposed that the both production and inhibition of H2S concentration beyond a threshold level could exert anticancer effects [10,11]. Threshold exert anticancer effects [10,11]

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