A mitochondrial targeted dual ratiometric near-infrared fluorescent probe based on ICT effect for the detection of SO2 derivative and its bioimaging

Kangshuo Xu; Na Tang; Furong Liu; Yin Ai; Haichang Ding; Congbin Fan; Gang Liu; Shouzhi Pu

doi:10.1016/j.saa.2024.124415

A mitochondrial targeted dual ratiometric near-infrared fluorescent probe based on ICT effect for the detection of SO₂ derivative and its bioimaging

Spectrochim Acta A Mol Biomol Spectrosc. 2024 May 6:317:124415. doi: 10.1016/j.saa.2024.124415. Online ahead of print.

Authors

Kangshuo Xu¹, Na Tang¹, Furong Liu¹, Yin Ai¹, Haichang Ding², Congbin Fan¹, Gang Liu³, Shouzhi Pu⁴

Affiliations

¹ Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China.
² Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China. Electronic address: dinghaichang@126.com.
³ Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China. Electronic address: liugang0926@163.com.
⁴ Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China; Department of Ecology and Environment, Yuzhang Normal University, Nanchang 330103, PR China. Electronic address: pushouzhi@tsinghua.org.cn.

PMID: 38733918
DOI: 10.1016/j.saa.2024.124415

Abstract

SO₂ derivatives play an important role in many metabolic processes, excessive ingestion of them can lead to serious complications of various diseases. In this work, a novel dual ratiometric NIR fluorescent probe XT-CHO based on ICT effect was synthesized for detecting SO₂ derivative. In the design of the probe, the α, β-unsaturated bond formed between benzopyran and coumarin was used as the reaction site for SO₂, meanwhile, the extended π-conjugate system promoted maximum emission wavelength of the probe up to 708 nm. Notably, the probe exhibited high selectivity and sensitivity for detecting SO₂, the limit of detection reached 2.13 nM and 58.5 nM in fluorescence spectra and UV-Vis absorption spectra, respectively. The reaction mechanism of SO₂ and XT-CHO had been verified by ¹H NMR, ESI-MS spectra and DFT calculation. Moreover, the probe was successfully applied in detecting endogenous and exogenous SO₂ in living cells and proved possessed the mitochondrial targeted ability.

Keywords: Imaging; Mitochondrial; NIR; Ratiometric probe; SO(2).