Cucurbit[8]uril-mediated triphenylamine coumarin derivative cascade assembly for NIR targeted cell imaging

A coumarin-modified tris[4-(4-pyridyl)phenyl]amine compound was encapsulated in the cavity of cucurbit[8]uril with a 2 : 3 stoichiometric ratio, which not only effectively enhances the guest fluorescence emission with a hypsochromic shift of about 51 nm by macrocycle confinement, but also allows cas...

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Bibliographic Details
Published in:New journal of chemistry 2024-08, Vol.48 (31), p.13685-13689
Main Authors: Yu, Zhen-Hai, Wang, Hui-Juan, Cheng, Qingwen, Zhang, Heng-Yi, Liu, Yu
Format: Article
Language:English
Subjects:
Assembly
Coumarin
Cyclodextrins
Energy transfer
Hyaluronic acid
Infrared imaging
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Summary:A coumarin-modified tris[4-(4-pyridyl)phenyl]amine compound was encapsulated in the cavity of cucurbit[8]uril with a 2 : 3 stoichiometric ratio, which not only effectively enhances the guest fluorescence emission with a hypsochromic shift of about 51 nm by macrocycle confinement, but also allows cascade assembly with β-cyclodextrin-grafted hyaluronic acid (HACD) to construct a ternary supramolecular network. Furthermore, doping of sulfo-cyanine 5 into the β-cyclodextrin cavity of HACD through host-guest interaction achieved a high efficiency Förster resonance energy transfer system from the supramolecular network to dyes, which was successfully applied to near-infrared mitochondria-targeted imaging in HeLa cells. A multilevel supramolecular cascade assembly has been constructed, and the ternary supramolecular network can undergo coassembly with Cy5 to display an efficient FRET platform, achieving targeted NIR cell imaging.
ISSN:1144-0546
1369-9261
DOI:10.1039/d4nj01843e