Thioanisole ester based logic gate cascade to control ROS-triggered micellar degradation

Irene Piergentili; Pepijn R. Bouwmans; Luuk Reinalda; Reece W. Lewis; Benjamin Klemm; Huanhuan Liu; Robin M. de Kruijff; Antonia G. Denkova; Rienk Eelkema

doi:10.1039/D2PY00207H

Thioanisole ester based logic gate cascade to control ROS-triggered micellar degradation†

Irene Piergentili,

^a Pepijn R. Bouwmans,^a Luuk Reinalda,^a Reece W. Lewis,

^a Benjamin Klemm,

^a Huanhuan Liu,^b Robin M. de Kruijff,

^b Antonia G. Denkova^b and Rienk Eelkema

*^a

Author affiliations

* Corresponding authors

^a Delft University of Technology, Department of Chemical Engineering, Van der Maasweg 9, 2629 HZ Delft, The Netherlands
E-mail: r.eelkema@tudelft.nl

^b Delft University of Technology, Department of Radiation Science and Technology, Mekelweg 15, 2629 JB Delft, The Netherlands

Abstract

In certain tumor and diseased tissues, reactive oxygen species (ROS), such as H₂O₂, are produced in higher concentrations than in healthy cells. Drug delivery and release systems that respond selectively to the presence of ROS, while maintaining their stability in “healthy” biological conditions, have great potential as on-site therapeutics. This study presents polymer micelles with 4-(methylthio)phenyl ester functionalities as a ROS-responsive reactivity switch. Oxidation of the thioether moieties triggers ester hydrolysis, exposing a hydrophylic carboxylate and leading to micellar disassembly. At 37 °C, the micelles fall apart on a timescale of days in the presence of 2 mM H₂O₂ and within hours at higher concentrations of H₂O₂ (60–600 mM). In the same time frame, the nanocarriers show no hydrolysis in oxidant-free physiological or mildly acidic conditions. This logic gate cascade behavior represents a step forward to realize drug delivery materials capable of selective response to a biomarker input.

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Article information

DOI: https://doi.org/10.1039/D2PY00207H
Article type: Paper
Submitted: 15 Feb 2022
Accepted: 29 Mar 2022
First published: 30 Mar 2022
This article is Open Access

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Polym. Chem., 2022,13, 2383-2390

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Thioanisole ester based logic gate cascade to control ROS-triggered micellar degradation

I. Piergentili, P. R. Bouwmans, L. Reinalda, R. W. Lewis, B. Klemm, H. Liu, R. M. de Kruijff, A. G. Denkova and R. Eelkema, Polym. Chem., 2022, 13, 2383 DOI: 10.1039/D2PY00207H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Polymer Chemistry

Thioanisole ester based logic gate cascade to control ROS-triggered micellar degradation†

Abstract

Supplementary files

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Thioanisole ester based logic gate cascade to control ROS-triggered micellar degradation

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