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Butyrylcholinesterase Responsive Supramolecular Prodrug with Targeted Near‐infrared Cellular Imaging Property

Butyrylcholinesterase Responsive Supramolecular Prodrug with Targeted Near‐infrared Cellular... An enzyme responsive supramolecular prodrug with near‐infrared targeted cell imaging property is constructed from organic dye (4‐(3‐(benzo[d]thiazol‐2‐yl)‐2‐hydroxy‐5‐methylstyryl)‐1‐methylpyridin‐1‐ium) (G), anti‐cancer drug chlorambucil (Cbl−G), water‐soluble cucurbit[7]uril (CB[7]) and biocompatible hyaluronic acid (HA). It is very interesting that CB[7] can not only associate Cbl−G to form supramolecular nanofibers, but also further assemble with targeter HA to form supramolecular nanoparticles with a diameter of about 200 nm. The loading efficiency of Cbl−G in the assembly is calculated to be as high as 98.2%. Cell experiments using HeLa and A549 cancer cells indicated that the prodrug nanoparticles are easily internalized into cancer cells via receptor‐mediated endocytosis, and disassembled under the action of butyrylcholinesterase by cutting the ester bond of prodrug, exhibiting a controlled drug release behavior as well as a simultaneous near‐infrared (NIR) fluorscence imaging in cancer cells. The present research might provide a feasible strategy for in situ monitoring drug delivery and NIR cellular imaging. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Butyrylcholinesterase Responsive Supramolecular Prodrug with Targeted Near‐infrared Cellular Imaging Property

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References (33)

Publisher
Wiley
Copyright
© 2021 Wiley‐VCH GmbH
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.202100541
Publisher site
See Article on Publisher Site

Abstract

An enzyme responsive supramolecular prodrug with near‐infrared targeted cell imaging property is constructed from organic dye (4‐(3‐(benzo[d]thiazol‐2‐yl)‐2‐hydroxy‐5‐methylstyryl)‐1‐methylpyridin‐1‐ium) (G), anti‐cancer drug chlorambucil (Cbl−G), water‐soluble cucurbit[7]uril (CB[7]) and biocompatible hyaluronic acid (HA). It is very interesting that CB[7] can not only associate Cbl−G to form supramolecular nanofibers, but also further assemble with targeter HA to form supramolecular nanoparticles with a diameter of about 200 nm. The loading efficiency of Cbl−G in the assembly is calculated to be as high as 98.2%. Cell experiments using HeLa and A549 cancer cells indicated that the prodrug nanoparticles are easily internalized into cancer cells via receptor‐mediated endocytosis, and disassembled under the action of butyrylcholinesterase by cutting the ester bond of prodrug, exhibiting a controlled drug release behavior as well as a simultaneous near‐infrared (NIR) fluorscence imaging in cancer cells. The present research might provide a feasible strategy for in situ monitoring drug delivery and NIR cellular imaging.

Journal

Asian Journal of Organic ChemistryWiley

Published: Dec 1, 2021

Keywords: cellular imaging; cucurbit[n]urils; enzyme responsive; hyaluronic acid; supramolecular prodrug

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