{"title":"设计和合成基于萘二甲酰亚胺的 CO 荧光探针,实现三色检测和开关响应","authors":"Junyu Zhang , Guoling Li , Xuguang Zhu, Huilong Xu, Zhonghai Ni, Yun Zhao","doi":"10.1016/j.tetlet.2024.155357","DOIUrl":null,"url":null,"abstract":"<div><div>Carbon monoxide (CO) fluorescent probes have attracted tremendous attention attributed to their low detection limit, high specificity, simple operation and good biocompatibility. However, the relationship between the molecular structure and the fluorescence response signal still needs to be systematically elucidated for different applications. Herein, three different CO fluorescent probes based on naphthalimide derivative with blue emission (B-NIA), green emission (G-NIA), and near-infrared emission (R-NIA) were designed and synthesized. Three-primary colors and opposite turn-on or turn-off fluorescent responses to CO were achieved by regulating the conjugation system of fluorophores and the position of fluorescent recognition group. The change of fluorescence response and sensing mechanism for CO detection was studied by theory calculation and mass spectrometry analysis. All the B/G/R-NIA possessed high sensitivity for CO detection. Notably, the R-NIA emerged with a noticeable NIR fluorescence response to CO with a low detection limit (0.61 µM) and high selectivity and relative pH stability. In addition, the R-NIA showed particularly low cytotoxicity and has been successfully used to detect CO in living cells. These studies provided the theoretical reference and technical route to synthesize fluorescent probes with different emission wavelengths and opposite fluorescent responses to CO for various application scenarios.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155357"},"PeriodicalIF":1.5000,"publicationDate":"2024-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Design and synthesis of naphthalimide-based CO fluorescent probes realizing tricolor detection and turn-on/off response\",\"authors\":\"Junyu Zhang , Guoling Li , Xuguang Zhu, Huilong Xu, Zhonghai Ni, Yun Zhao\",\"doi\":\"10.1016/j.tetlet.2024.155357\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Carbon monoxide (CO) fluorescent probes have attracted tremendous attention attributed to their low detection limit, high specificity, simple operation and good biocompatibility. However, the relationship between the molecular structure and the fluorescence response signal still needs to be systematically elucidated for different applications. Herein, three different CO fluorescent probes based on naphthalimide derivative with blue emission (B-NIA), green emission (G-NIA), and near-infrared emission (R-NIA) were designed and synthesized. Three-primary colors and opposite turn-on or turn-off fluorescent responses to CO were achieved by regulating the conjugation system of fluorophores and the position of fluorescent recognition group. The change of fluorescence response and sensing mechanism for CO detection was studied by theory calculation and mass spectrometry analysis. All the B/G/R-NIA possessed high sensitivity for CO detection. Notably, the R-NIA emerged with a noticeable NIR fluorescence response to CO with a low detection limit (0.61 µM) and high selectivity and relative pH stability. In addition, the R-NIA showed particularly low cytotoxicity and has been successfully used to detect CO in living cells. These studies provided the theoretical reference and technical route to synthesize fluorescent probes with different emission wavelengths and opposite fluorescent responses to CO for various application scenarios.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":\"152 \",\"pages\":\"Article 155357\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-11-03\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403924004520\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004520","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
一氧化碳(CO)荧光探针因其检测限低、特异性强、操作简单和良好的生物相容性而备受关注。然而,针对不同的应用,分子结构与荧光响应信号之间的关系仍有待系统阐明。本文设计并合成了基于萘二甲酰亚胺衍生物的三种不同的 CO 荧光探针,它们分别具有蓝色发射(B-NIA)、绿色发射(G-NIA)和近红外发射(R-NIA)。通过调节荧光团的共轭体系和荧光识别基团的位置,实现了对 CO 的三基色和相反的开启或关闭荧光响应。通过理论计算和质谱分析,研究了荧光响应的变化和检测 CO 的传感机制。所有 B/G/R-NIA 都具有较高的 CO 检测灵敏度。值得注意的是,R-NIA 对 CO 具有明显的近红外荧光响应,检测限低(0.61 µM),且具有高选择性和相对 pH 稳定性。此外,R-NIA 的细胞毒性特别低,已成功用于检测活细胞中的 CO。这些研究为合成不同发射波长、对一氧化碳具有相反荧光响应的荧光探针提供了理论参考和技术路线,可用于各种应用场景。
Design and synthesis of naphthalimide-based CO fluorescent probes realizing tricolor detection and turn-on/off response
Carbon monoxide (CO) fluorescent probes have attracted tremendous attention attributed to their low detection limit, high specificity, simple operation and good biocompatibility. However, the relationship between the molecular structure and the fluorescence response signal still needs to be systematically elucidated for different applications. Herein, three different CO fluorescent probes based on naphthalimide derivative with blue emission (B-NIA), green emission (G-NIA), and near-infrared emission (R-NIA) were designed and synthesized. Three-primary colors and opposite turn-on or turn-off fluorescent responses to CO were achieved by regulating the conjugation system of fluorophores and the position of fluorescent recognition group. The change of fluorescence response and sensing mechanism for CO detection was studied by theory calculation and mass spectrometry analysis. All the B/G/R-NIA possessed high sensitivity for CO detection. Notably, the R-NIA emerged with a noticeable NIR fluorescence response to CO with a low detection limit (0.61 µM) and high selectivity and relative pH stability. In addition, the R-NIA showed particularly low cytotoxicity and has been successfully used to detect CO in living cells. These studies provided the theoretical reference and technical route to synthesize fluorescent probes with different emission wavelengths and opposite fluorescent responses to CO for various application scenarios.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.