Water-Soluble Aromatic Nanobelt with Unique Cellular Internalization

被引:0
|
作者
Gunther, Konstantin [1 ,2 ]
Kono, Hideya [1 ]
Shudo, Hiroki [1 ]
Shimizu, Daisuke [1 ]
Isoda, Reika [3 ]
Nakamura, Masayoshi [3 ]
Yagi, Akiko [1 ,3 ]
Amaike, Kazuma [4 ]
Itami, Kenichiro [3 ,4 ]
机构
[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Nagoya, Aichi 4648602, Japan
[2] Humboldt Univ, Dept Chem, Brook Taylor Str 2, D-12489 Berlin, Germany
[3] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Nagoya, Aichi 4648602, Japan
[4] RIKEN, RIKEN Cluster Pioneering Res, Mol Creat Lab, Wako, Saitama 3510198, Japan
关键词
aromatic compounds; bioimaging; cycloparaphenylene; late-stage functionalization; nanobelt; CARBON; NANOHOOPS;
D O I
10.1002/anie.202414645
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
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页数:5
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