Theoretical Investigations on the Sensing Mechanism of Dicyanoisophorone Fluorescent Probe for the Detection of Hydrogen Sulfide

IF 2.6 4区 化学 Q2 BIOCHEMICAL RESEARCH METHODS
Zhicheng Xia, Honghong Xu, Anran Huang, Wenxuan Hao, Dongxia Wu, Shibin Yin, Haixiang He
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Abstract

As one of the biomolecules, hydrogen sulfide (H2S) has received a lot of attention. Recent studies have shown that endogenous hydrogen sulfide plays different roles in different organs in biological systems. Fluorescent probe technology has been widely adopted due to its many advantages such as low cost, simple operation, and high sensitivity. Among many probes, dicyanoisophorone fluorophore is often used in probe design for real-time detection of endogenous H2S due to the large Stokes shift and long fluorescence emission wavelength. In this paper, the fluorescence sensing mechanism of dicyanoisophorone-like probe L and its product 3 with near-infrared fluorescence emission has been theoretically investigated by using theory methods. The analysis of infrared (IR) vibration spectra and reduced density gradient (RDG) showed that the hydrogen bond of the enolic structure of product 3 was significantly enhanced in the S1 state. The spectroscopic information revealed that the emission of NIR fluorescence originated from the keto structure of the product. Finally, potential energy curves and frontier molecular orbitals diagrams showed that the fluorescence quenching phenomenon of the probe L was attributed to the photoinduced electron transfer (PET) process, whereas the product 3 generated after the detection of H2S undergoes the excited state intramolecular proton transfer (ESIPT) process.

Abstract Image

二氰异佛尔酮荧光探针检测硫化氢的传感机制理论研究
作为生物大分子之一,硫化氢(H2S)受到了广泛关注。最新研究表明,内源性硫化氢在生物系统的不同器官中发挥着不同的作用。荧光探针技术具有成本低、操作简单、灵敏度高等诸多优点,已被广泛采用。在众多探针中,二氰异佛尔酮荧光团因具有较大的斯托克斯位移和较长的荧光发射波长,常被用于实时检测内源性硫化氢的探针设计中。本文利用理论方法对具有近红外荧光发射的类二氰基异佛尔酮探针 L 及其产物 3 的荧光传感机理进行了理论研究。红外振动光谱和还原密度梯度(RDG)分析表明,产物 3 的烯醇结构氢键在 S1 状态下显著增强。光谱信息显示,近红外荧光的发射源于产物的酮结构。最后,势能曲线和前沿分子轨道图显示,探针 L 的荧光淬灭现象归因于光诱导电子转移(PET)过程,而检测 H2S 后生成的产物 3 则经历了激发态分子内质子转移(ESIPT)过程。
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来源期刊
Journal of Fluorescence
Journal of Fluorescence 化学-分析化学
CiteScore
4.60
自引率
7.40%
发文量
203
审稿时长
5.4 months
期刊介绍: Journal of Fluorescence is an international forum for the publication of peer-reviewed original articles that advance the practice of this established spectroscopic technique. Topics covered include advances in theory/and or data analysis, studies of the photophysics of aromatic molecules, solvent, and environmental effects, development of stationary or time-resolved measurements, advances in fluorescence microscopy, imaging, photobleaching/recovery measurements, and/or phosphorescence for studies of cell biology, chemical biology and the advanced uses of fluorescence in flow cytometry/analysis, immunology, high throughput screening/drug discovery, DNA sequencing/arrays, genomics and proteomics. Typical applications might include studies of macromolecular dynamics and conformation, intracellular chemistry, and gene expression. The journal also publishes papers that describe the synthesis and characterization of new fluorophores, particularly those displaying unique sensitivities and/or optical properties. In addition to original articles, the Journal also publishes reviews, rapid communications, short communications, letters to the editor, topical news articles, and technical and design notes.
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