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Background <p>Hydrogen sulfide (H<sub>2</sub>S) is a critical reactive sulfur species that serves a vital role in cellular signaling, cardiovascular regulation, and oxidative stress protection. To detect the physiological presence of this small molecule, a new indole-nitronaphthalimide hybrid (INN), wherein the two core units are linked through an acetamide spacer, was synthesized through an imidation reaction between indole-3-acetic acid hydrazide and 4-nitro-1,8-naphthalic anhydride.</p> Results <p>INN demonstrated sensitivity towards H<sub>2</sub>S in electrochemical analysis with a detection limit of 11.04 nM. Electrochemical measurements with INN-coated electrodes in solutions of different pH levels facilitated the elucidation of the underlying redox mechanism. While most fluorescence probes are based on a simple turn-on mode, INN exhibited ratiometric fluorescence sensing of H<sub>2</sub>S at physiological pH with a detection threshold of 7.71 mM. The reduction of the nitro group in INN to amino in the presence of H<sub>2</sub>S induces a ratiometric change in the fluorescence emission, transitioning from 343 to 547&#xa0;nm. Live imaging in HEK293T cells confirmed that INN exhibits strong fluorescence in the red channel, highlighting its capability to detect H<sub>2</sub>S under physiological conditions.</p> Significance <p>This small-molecule probe serves as a valuable tool for studying H<sub>2</sub>S-mediated biological processes and holds great potential for advancing sulfur chemistry.</p> Graphical abstract <p></p>

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Indole-functionalized naphthalimide: a dual electrochemical and ratiometric fluorescent sensor for detection of hydrogen sulfide

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年12月1日

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  • Ranjana M.,
  • Anshuman Bera,
  • Namita N. Kashyap,
  • Dhanya Sunil,
  • Sudhakar Y. N.,
  • Sivaranjana Reddy Vennapusa,
  • Dinesh Upadhya,
  • Suresh D. Kulkarni

摘要

Background

Hydrogen sulfide (H2S) is a critical reactive sulfur species that serves a vital role in cellular signaling, cardiovascular regulation, and oxidative stress protection. To detect the physiological presence of this small molecule, a new indole-nitronaphthalimide hybrid (INN), wherein the two core units are linked through an acetamide spacer, was synthesized through an imidation reaction between indole-3-acetic acid hydrazide and 4-nitro-1,8-naphthalic anhydride.

Results

INN demonstrated sensitivity towards H2S in electrochemical analysis with a detection limit of 11.04 nM. Electrochemical measurements with INN-coated electrodes in solutions of different pH levels facilitated the elucidation of the underlying redox mechanism. While most fluorescence probes are based on a simple turn-on mode, INN exhibited ratiometric fluorescence sensing of H2S at physiological pH with a detection threshold of 7.71 mM. The reduction of the nitro group in INN to amino in the presence of H2S induces a ratiometric change in the fluorescence emission, transitioning from 343 to 547 nm. Live imaging in HEK293T cells confirmed that INN exhibits strong fluorescence in the red channel, highlighting its capability to detect H2S under physiological conditions.

Significance

This small-molecule probe serves as a valuable tool for studying H2S-mediated biological processes and holds great potential for advancing sulfur chemistry.

Graphical abstract