Design and Application of Fluorescent Probes Based on Flavonoid Dyes for Cysteine Detection.

IF 2.6 4区 化学 Q2 BIOCHEMICAL RESEARCH METHODS
Jing Liu, Xiaorui Cao, Tiantian Liu, Yang Zhang, Xiaomeng Jiao, Hongpeng Zhang, Yinjuan Bai
{"title":"Design and Application of Fluorescent Probes Based on Flavonoid Dyes for Cysteine Detection.","authors":"Jing Liu, Xiaorui Cao, Tiantian Liu, Yang Zhang, Xiaomeng Jiao, Hongpeng Zhang, Yinjuan Bai","doi":"10.1007/s10895-025-04226-w","DOIUrl":null,"url":null,"abstract":"<p><p>As an important reactive sulfur species, cysteine plays a crucial role in maintaining the body's redox homeostasis and regulating protein function. Its content in organisms can serve as signaling molecules to directly or indirectly detect certain diseases. Therefore, based on the Michael addition mechanism, five flavonoid fluorescent probes HFL1-5 were designed and synthesized to detect cysteine. Through specific descriptions of IR,<sup>1</sup>H NMR and HRMS experiments, the recognition mechanism of cysteine by HFL was studied, demonstrating that HFL1-5 could generate flavonol derivatives with strong fluorescence emission through addition-cyclization-removal. The probes were evaluated for large Stokes shift, sensitivity, stability, specificity and cytotoxicity. Finally, the best performing HFL5 was selected for cell imaging experiments and successfully applied to the imaging of endogenous and exogenous cysteine in L929 cells. This study indicates that HFL has great potential for application in detecting cysteine. We hope to provide experimental data support for future structure-activity research.</p>","PeriodicalId":15800,"journal":{"name":"Journal of Fluorescence","volume":" ","pages":""},"PeriodicalIF":2.6000,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Fluorescence","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s10895-025-04226-w","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMICAL RESEARCH METHODS","Score":null,"Total":0}
引用次数: 0

Abstract

As an important reactive sulfur species, cysteine plays a crucial role in maintaining the body's redox homeostasis and regulating protein function. Its content in organisms can serve as signaling molecules to directly or indirectly detect certain diseases. Therefore, based on the Michael addition mechanism, five flavonoid fluorescent probes HFL1-5 were designed and synthesized to detect cysteine. Through specific descriptions of IR,1H NMR and HRMS experiments, the recognition mechanism of cysteine by HFL was studied, demonstrating that HFL1-5 could generate flavonol derivatives with strong fluorescence emission through addition-cyclization-removal. The probes were evaluated for large Stokes shift, sensitivity, stability, specificity and cytotoxicity. Finally, the best performing HFL5 was selected for cell imaging experiments and successfully applied to the imaging of endogenous and exogenous cysteine in L929 cells. This study indicates that HFL has great potential for application in detecting cysteine. We hope to provide experimental data support for future structure-activity research.

基于类黄酮染料的半胱氨酸荧光探针的设计与应用。
半胱氨酸作为一种重要的活性硫物质,在维持机体氧化还原稳态和调节蛋白质功能方面起着至关重要的作用。它在生物体中的含量可以作为信号分子直接或间接检测某些疾病。因此,基于Michael加成机理,设计合成了5个类黄酮荧光探针HFL1-5,用于检测半胱氨酸。通过IR、1H NMR和HRMS实验的具体描述,研究了HFL1-5对半胱氨酸的识别机理,证明HFL1-5可以通过加成-环化-去除生成具有强荧光发射的黄酮醇衍生物。对探针进行了大斯托克斯位移、灵敏度、稳定性、特异性和细胞毒性评估。最后选择表现最好的HFL5进行细胞成像实验,成功应用于L929细胞内源性和外源性半胱氨酸的成像。本研究表明HFL在检测半胱氨酸方面具有很大的应用潜力。希望为今后的构效研究提供实验数据支持。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
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.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信