{"title":"Water-Soluble Aromatic Nanobelt with Unique Cellular Internalization","authors":"Konstantin Günther, Hideya Kono, Hiroki Shudo, Daisuke Shimizu, Reika Isoda, Masayoshi Nakamura, Akiko Yagi, Kazuma Amaike, Kenichiro Itami","doi":"10.1002/anie.202414645","DOIUrl":null,"url":null,"abstract":"A water-soluble aromatic nanobelt was synthesized, and its cellular uptake behavior in HeLa cells was investigated. The late-stage functionalization of the parent methylene-bridged [6]cycloparaphenylene ([6]MCPP) provided an easily accessible alkyne-functionalized nanobelt in a single reaction step. The alkyne-substituted [6]MCPP was subjected to Cu-catalyzed azide–alkyne cycloaddition by using a dye-attached azide to obtain a water-soluble aromatic nanobelt. Cell-imaging experiments on the synthesized nanobelt in HeLa cells revealed stop-and-go cellular uptake dynamics. Similar experiments with control molecules and theoretical studies indicated that the unique dynamics of the nanobelt was derived from the belt-shaped structure.","PeriodicalId":125,"journal":{"name":"Angewandte Chemie International Edition","volume":null,"pages":null},"PeriodicalIF":16.1000,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Angewandte Chemie International Edition","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/anie.202414645","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
A water-soluble aromatic nanobelt was synthesized, and its cellular uptake behavior in HeLa cells was investigated. The late-stage functionalization of the parent methylene-bridged [6]cycloparaphenylene ([6]MCPP) provided an easily accessible alkyne-functionalized nanobelt in a single reaction step. The alkyne-substituted [6]MCPP was subjected to Cu-catalyzed azide–alkyne cycloaddition by using a dye-attached azide to obtain a water-soluble aromatic nanobelt. Cell-imaging experiments on the synthesized nanobelt in HeLa cells revealed stop-and-go cellular uptake dynamics. Similar experiments with control molecules and theoretical studies indicated that the unique dynamics of the nanobelt was derived from the belt-shaped structure.
我们合成了一种水溶性芳香族纳米带，并研究了它在 HeLa 细胞中的细胞吸收行为。母体亚甲基桥接[6]环联苯（[6]MCPP）的后期官能化仅需一个反应步骤就能提供一种易于获得的炔烃官能化纳米带。炔基取代的 [6]MCPP 在铜催化下，通过使用染料连接的叠氮化物进行叠氮-炔基环加成反应，得到水溶性芳香族纳米带。在 HeLa 细胞中对合成的纳米带进行的细胞成像实验显示了细胞摄取的停停走走的动态变化。用对照分子进行的类似实验和理论研究表明，纳米带独特的动力学特性来自于带状结构。
期刊介绍：
Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.
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