A two photon fluorescent probe for highly selective detection and endogenous imaging of hydrogen sulfide

Wan-Yu Yang; Kathiresan Anusuyadevi; Ping-Hsuan Lu; Natesan Thirumalaivasan; Wen- Hsuan Lin; Sivan Velmathi; Shu-Pao Wu

doi:10.1016/j.saa.2022.121043

A two photon fluorescent probe for highly selective detection and endogenous imaging of hydrogen sulfide

Spectrochim Acta A Mol Biomol Spectrosc. 2022 May 15:273:121043. doi: 10.1016/j.saa.2022.121043. Epub 2022 Feb 15.

Authors

Wan-Yu Yang¹, Kathiresan Anusuyadevi², Ping-Hsuan Lu¹, Natesan Thirumalaivasan¹, Wen- Hsuan Lin¹, Sivan Velmathi³, Shu-Pao Wu⁴

Affiliations

¹ Department of Applied Chemistry, National Yang Ming Chiao Tung University, Hsinchu 30010, Taiwan.
² Organic and Polymer Synthesis Laboratory, Department of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India.
³ Organic and Polymer Synthesis Laboratory, Department of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India. Electronic address: velmathis@nitt.edu.
⁴ Department of Applied Chemistry, National Yang Ming Chiao Tung University, Hsinchu 30010, Taiwan; Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan. Electronic address: spwu@nycu.edu.tw.

PMID: 35189492
DOI: 10.1016/j.saa.2022.121043

Abstract

Hydrogen sulfide (H₂S), one of redox-active sulfur species, is known as a signaling molecule and an antioxidant in biological tissues to maintain cellular functions. The development of selective and sensitive H₂S detection is important to understand the role of H₂S in vivo. Herein, a new two-photon probe NNE was developed to detect hydrogen sulfide using 6-acetyl-N-methyl-2-naphthylamine with an attachment of 7-nitrobenzo-oxadiazole. The probe NNE exhibits high selectivity towards hydrogen sulfide over other anions. Nucleophilic substitution of H₂S leads to a turn-on response with 28-fold enhancement in quantum yield (from 0.004 to 0.117). NNE shows a high sensitivity towards hydrogen sulfide with an extremely low detection limit at 6.8 nM. Furthermore, the probe NNE exhibits two-photon excited fluorescence, making it a suitable probe for monitoring H₂S distribution in live cells and tissues without background fluorescence interference.

Keywords: Endogenous cell imaging; Fluorescent probe; H(2)S; Two-photon.

MeSH terms

Diagnostic Imaging
Fluorescent Dyes
HeLa Cells
Humans
Hydrogen Sulfide*
Optical Imaging
Oxidation-Reduction
Photons

Substances

Fluorescent Dyes
Hydrogen Sulfide