Pavel A. Panchenko, Marina A. Pavlova, Anastasija V. Efremenko, Uliana A. Kutsevalova, Maria A. Ustimova, Alexey V. Feofanov, Yuri V. Fedorov, Olga A. Fedorova
{"title":"基于共振能量转移和“1,8-萘酰亚胺-苯基吡啶”二元二聚胺受体的水溶液中铜(II)阳离子的选择性和敏感比例荧光探针","authors":"Pavel A. Panchenko, Marina A. Pavlova, Anastasija V. Efremenko, Uliana A. Kutsevalova, Maria A. Ustimova, Alexey V. Feofanov, Yuri V. Fedorov, Olga A. Fedorova","doi":"10.1007/s11705-025-2594-6","DOIUrl":null,"url":null,"abstract":"<div><p>Development of ratiometric fluorescent probes for Cu<sup>2+</sup> in aqueous solutions and biological systems remains the challenging task, given that Cu<sup>2+</sup> commonly acts as an efficient fluorescence quencher. In this work, a novel dyad compound NI-SP bearing energy donor naphthalimide and energy acceptor styrylpyridine chromophore has been prepared using azide-alkyne click reaction. The photophysical properties of NI-SP and its coordination with Cu<sup>2+</sup> have been investigated by the absorption and fluorescent spectroscopy. Upon addition of Cu<sup>2+</sup> to a solution of NI-SP, the long wavelength emission peak of styrylpyridine (600 nm) was quenched, whereas the fluorescence of naphthalimide (450 nm) was enhanced due to a decrease in resonance energy transfer efficiency between the chromophores in the (NI-SP)·Cu<sup>2+</sup> complex. The observed spectral changes enable ratiometric detection of Cu<sup>2+</sup> by the registration of the ratio of fluorescence intensities <i>I</i><sub>450</sub>/<i>I</i><sub>600</sub>. The probe exhibited high selectivity toward Cu<sup>2+</sup> in the tested conditions. The detection limit was determined at 120 nmol·L<sup>−1</sup>, and the stability constant for (NI-SP)·Cu<sup>2+</sup> was found to be 3.0 × 10<sup>6</sup> L·mol<sup>−1</sup>. Bioimaging experiments showed the NI-SP could penetrate human lung adenocarcinoma A549 cells, accumulate in mitochondria, and respond to the presence of Cu<sup>2+</sup> via the changes in the fluorescence intensity of styrylpyridine fragment.\n</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":571,"journal":{"name":"Frontiers of Chemical Science and Engineering","volume":"19 9","pages":""},"PeriodicalIF":4.5000,"publicationDate":"2025-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Selective and sensitive ratiometric fluorescent probe for copper(II) cations in an aqueous solution based on resonance energy transfer and “1,8-naphthalimide–styrylpyridine” dyad bearing dipicolylamine receptor\",\"authors\":\"Pavel A. Panchenko, Marina A. Pavlova, Anastasija V. Efremenko, Uliana A. Kutsevalova, Maria A. Ustimova, Alexey V. Feofanov, Yuri V. Fedorov, Olga A. Fedorova\",\"doi\":\"10.1007/s11705-025-2594-6\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Development of ratiometric fluorescent probes for Cu<sup>2+</sup> in aqueous solutions and biological systems remains the challenging task, given that Cu<sup>2+</sup> commonly acts as an efficient fluorescence quencher. In this work, a novel dyad compound NI-SP bearing energy donor naphthalimide and energy acceptor styrylpyridine chromophore has been prepared using azide-alkyne click reaction. The photophysical properties of NI-SP and its coordination with Cu<sup>2+</sup> have been investigated by the absorption and fluorescent spectroscopy. Upon addition of Cu<sup>2+</sup> to a solution of NI-SP, the long wavelength emission peak of styrylpyridine (600 nm) was quenched, whereas the fluorescence of naphthalimide (450 nm) was enhanced due to a decrease in resonance energy transfer efficiency between the chromophores in the (NI-SP)·Cu<sup>2+</sup> complex. The observed spectral changes enable ratiometric detection of Cu<sup>2+</sup> by the registration of the ratio of fluorescence intensities <i>I</i><sub>450</sub>/<i>I</i><sub>600</sub>. The probe exhibited high selectivity toward Cu<sup>2+</sup> in the tested conditions. The detection limit was determined at 120 nmol·L<sup>−1</sup>, and the stability constant for (NI-SP)·Cu<sup>2+</sup> was found to be 3.0 × 10<sup>6</sup> L·mol<sup>−1</sup>. Bioimaging experiments showed the NI-SP could penetrate human lung adenocarcinoma A549 cells, accumulate in mitochondria, and respond to the presence of Cu<sup>2+</sup> via the changes in the fluorescence intensity of styrylpyridine fragment.\\n</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":571,\"journal\":{\"name\":\"Frontiers of Chemical Science and Engineering\",\"volume\":\"19 9\",\"pages\":\"\"},\"PeriodicalIF\":4.5000,\"publicationDate\":\"2025-07-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Frontiers of Chemical Science and Engineering\",\"FirstCategoryId\":\"5\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s11705-025-2594-6\",\"RegionNum\":3,\"RegionCategory\":\"工程技术\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"ENGINEERING, CHEMICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Frontiers of Chemical Science and Engineering","FirstCategoryId":"5","ListUrlMain":"https://link.springer.com/article/10.1007/s11705-025-2594-6","RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"ENGINEERING, CHEMICAL","Score":null,"Total":0}
Selective and sensitive ratiometric fluorescent probe for copper(II) cations in an aqueous solution based on resonance energy transfer and “1,8-naphthalimide–styrylpyridine” dyad bearing dipicolylamine receptor
Development of ratiometric fluorescent probes for Cu2+ in aqueous solutions and biological systems remains the challenging task, given that Cu2+ commonly acts as an efficient fluorescence quencher. In this work, a novel dyad compound NI-SP bearing energy donor naphthalimide and energy acceptor styrylpyridine chromophore has been prepared using azide-alkyne click reaction. The photophysical properties of NI-SP and its coordination with Cu2+ have been investigated by the absorption and fluorescent spectroscopy. Upon addition of Cu2+ to a solution of NI-SP, the long wavelength emission peak of styrylpyridine (600 nm) was quenched, whereas the fluorescence of naphthalimide (450 nm) was enhanced due to a decrease in resonance energy transfer efficiency between the chromophores in the (NI-SP)·Cu2+ complex. The observed spectral changes enable ratiometric detection of Cu2+ by the registration of the ratio of fluorescence intensities I450/I600. The probe exhibited high selectivity toward Cu2+ in the tested conditions. The detection limit was determined at 120 nmol·L−1, and the stability constant for (NI-SP)·Cu2+ was found to be 3.0 × 106 L·mol−1. Bioimaging experiments showed the NI-SP could penetrate human lung adenocarcinoma A549 cells, accumulate in mitochondria, and respond to the presence of Cu2+ via the changes in the fluorescence intensity of styrylpyridine fragment.
期刊介绍:
Frontiers of Chemical Science and Engineering presents the latest developments in chemical science and engineering, emphasizing emerging and multidisciplinary fields and international trends in research and development. The journal promotes communication and exchange between scientists all over the world. The contents include original reviews, research papers and short communications. Coverage includes catalysis and reaction engineering, clean energy, functional material, nanotechnology and nanoscience, biomaterials and biotechnology, particle technology and multiphase processing, separation science and technology, sustainable technologies and green processing.