Reduction-Triggered Transformation of Disulfide-Containing Micelles at Chemically Tunable Rates

Angewandte Chemie
Zhengyu DengShiyong Liu

Abstract

A dilemma exists between the circulation stability and cargo release/mass diffusion at desired sites when designing delivery nanocarriers and in vivo nanoreactors. Reported herein are disulfide-crosslinked (DCL) micelles exhibiting reduction-triggered switching of crosslinking modules and synchronized hydrophobic-to-hydrophilic transition. Tumor cell targeted DCL micelles undergo cytoplasmic milieu triggered disulfide cleavage and self-immolative decaging reactions at chemically adjustable rates, generating primary amine moieties. Extensive amidation reactions with neighboring ester moieties then occur because of the high local concentration and suppression of the apparent amine pKa  value within the hydrophobic cores, thus leading to the transformation of crosslinking modules and formation of tracelessly crosslinked (TCL) micelles, with hydrophilic cores, inside live cells. We further integrate this design principle with theranostic nanocarriers for selective intracellular drug transport guided by enhanced magnetic resonance (MR) imaging performance.

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Citations

Jun 13, 2018·Chemistry : a European Journal·Guhuan LiuShiyong Liu
Apr 4, 2019·Biomaterials Science·Jingyan ZhangMingdi Yang
May 18, 2019·Chembiochem : a European Journal of Chemical Biology·Bang WangYulin Li
Nov 23, 2019·Macromolecular Rapid Communications·Zhengyu DengShiyong Liu
Aug 14, 2019·Frontiers in Chemistry·Jian ChengJinming Hu
Nov 7, 2020·Wiley Interdisciplinary Reviews. Nanomedicine and Nanobiotechnology·Patrícia F MonteiroCameron Alexander
Mar 23, 2021·Macromolecular Rapid Communications·Siyang WangMarek W Urban
Apr 15, 2020·Journal of Agricultural and Food Chemistry·Lianghao ChengJienan Chen
Dec 10, 2019·Bioconjugate Chemistry·Zhengyu DengWeihong Tan
Oct 16, 2021·Biomacromolecules·Daniel A PatersonAllan B Gamble
Oct 26, 2021·Organic Letters·Xhenti FerhatiFrancisco Corzana

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