Issue 5, 2021

Mechanochemical activation of disulfide-based multifunctional polymers for theranostic drug release

Abstract

Drug delivery systems responsive to physicochemical stimuli allow spatiotemporal control over drug activity to overcome limitations of systemic drug administration. Alongside, the non-invasive real-time tracking of drug release and uptake remains challenging as pharmacophore and reporter function are rarely unified within one molecule. Here, we present an ultrasound-responsive release system based on the mechanochemically induced 5-exo-trig cyclization upon scission of disulfides bearing cargo molecules attached via β-carbonate linker within the center of a water soluble polymer. In this bifunctional theranostic approach, we release one reporter molecule per drug molecule to quantitatively track drug release and distribution within the cell in real-time. We use N-butyl-4-hydroxy-1,8-naphthalimide and umbelliferone as fluorescent reporter molecules to accompany the release of camptothecin and gemcitabine as clinically employed anticancer agents. The generality of this approach paves the way for the theranostic release of a variety of probes and drugs by ultrasound.

Graphical abstract: Mechanochemical activation of disulfide-based multifunctional polymers for theranostic drug release

Associated articles

Supplementary files

Article information

Article type
Edge Article
Submitted
03 Nov 2020
Accepted
01 Dec 2020
First published
15 Dec 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 1668-1674

Mechanochemical activation of disulfide-based multifunctional polymers for theranostic drug release

Z. Shi, Q. Song, R. Göstl and A. Herrmann, Chem. Sci., 2021, 12, 1668 DOI: 10.1039/D0SC06054B

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