{"title":"Macrocycle Formation-Mediated Augmentation in Reactive Oxygen Species Production","authors":"Ao Liu, Youtao Xin, Yong-Kang Zhu, Yuan-Hang Jin, Yue Yang, Hongzhu Chen, Meng-Hao Li, Xin-Yue Lou, Xin Wang, Hui Gao, Ying-Wei Yang","doi":"10.1039/d5sc06637a","DOIUrl":null,"url":null,"abstract":"While the synthesis of methylene-bridged fluorescent macrocycles has attracted significant research interest, their ability to generate reactive oxygen species (ROS) remains relatively unexplored. Herein, we present a strategy for constructing multifunctional macrocycles through backbone functionalization and successfully synthesize a new class of [2]terphenyl-extended pillar[6]arenes. Upon incorporating benzothiadiazole, highly fluorescent macrocycles with aggregation-induced emission enhancement characteristics, i.e., [2]terphenyl-benzothiadiazole-extended pillar[6]arenes, were obtained. Subsequent studies on modulating side-chain modifications have revealed distinct singlet oxygen (1O2) generation capabilities. Notably, quaternary ammonium-functionalized macrocycles show lower quantum yields yet superior 1O2 generation efficiency under light irradiation compared to their ethoxy-modified counterparts and the acyclic building block, while retaining targeted fluorescence imaging capabilities. Significantly, the supramolecular synergy between photodynamic action and ceftizoxime sodium drug complexation drastically enhances antibacterial efficacy compared to individual modalities. This study highlights the potential of quaternary ammonium-functionalized fluorescent macrocycles in 1O2 generation and offers promising new avenues for developing antibacterial drugs for biomedical applications.","PeriodicalId":9909,"journal":{"name":"Chemical Science","volume":"4 1","pages":""},"PeriodicalIF":7.4000,"publicationDate":"2025-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Science","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5sc06637a","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
While the synthesis of methylene-bridged fluorescent macrocycles has attracted significant research interest, their ability to generate reactive oxygen species (ROS) remains relatively unexplored. Herein, we present a strategy for constructing multifunctional macrocycles through backbone functionalization and successfully synthesize a new class of [2]terphenyl-extended pillar[6]arenes. Upon incorporating benzothiadiazole, highly fluorescent macrocycles with aggregation-induced emission enhancement characteristics, i.e., [2]terphenyl-benzothiadiazole-extended pillar[6]arenes, were obtained. Subsequent studies on modulating side-chain modifications have revealed distinct singlet oxygen (1O2) generation capabilities. Notably, quaternary ammonium-functionalized macrocycles show lower quantum yields yet superior 1O2 generation efficiency under light irradiation compared to their ethoxy-modified counterparts and the acyclic building block, while retaining targeted fluorescence imaging capabilities. Significantly, the supramolecular synergy between photodynamic action and ceftizoxime sodium drug complexation drastically enhances antibacterial efficacy compared to individual modalities. This study highlights the potential of quaternary ammonium-functionalized fluorescent macrocycles in 1O2 generation and offers promising new avenues for developing antibacterial drugs for biomedical applications.
期刊介绍:
Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.