Selenol-Based Nucleophilic Reaction for the Preparation of Reactive Oxygen Species-Responsive Amphiphilic Diblock Copolymers.

Xiaowei An,Xiangqiang Pan,Jian Zhu,Weihong Lu,Xiulin Zhu

doi:10.3390/polym11050827

Xiaowei An, Xiangqiang Pan + Show 3 more

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https://doi.org/10.3390/polym11050827

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Journal: Polymers	Publication Date: May 8, 2019
Citations: 1	License type: CC BY 4.0

Affiliation: Soochow University

Abstract

Selenide-containing amphiphilic copolymers have shown significant potential for application in drug release systems. Herein, we present a methodology for the design of a reactive oxygen species-responsive amphiphilic diblock selenide-labeled copolymer. This copolymer with controlled molecular weight and narrow molecular weight distribution was prepared by sequential organoselenium-mediated reversible addition fragmentation chain transfer (Se-RAFT) polymerization and selenol-based nucleophilic reaction. Nuclear magnetic resonance (NMR) and matrix-assisted laser desorption/ionization time-to-flight (MALDI-TOF) techniques were used to characterize its structure. Its corresponding nanomicelles successfully formed through self-assembly from the copolymer itself. Such nanomicelles could rapidly disassemble under oxidative conditions due to the fragmentation of the Se–C bond. Therefore, this type of nanomicelle based on selenide-labeled amphiphilic copolymers potentially provides a new platform for drug delivery.

Highlights

IntroductionSelenium shows versatile properties owing to its larger atomic radius and relatively lower electronegativity [1]
Compared with sulfur, selenium shows versatile properties owing to its larger atomic radius and relatively lower electronegativity [1]
A straightforward protocol for the synthesis of an oxidation-sensitive selenide-containing block copolymer has been developed on protocol the basis for of sequential organoselenium-mediated reversible addition fragmentation chain transfer (Se-RAFT)

Summary

Introduction

Selenium shows versatile properties owing to its larger atomic radius and relatively lower electronegativity [1]. Selenium-containing polymers have attracted a great deal of attention in recent years and have been widely used as photoelectric materials, adaptive materials, and biomedical materials [2,3]. Selenophene polymers have been considered to be effective photoelectric materials which may be widely used in solar cells, molecular switches, thin film transistors, etc. Diselenide-containing adaptive materials were successfully incorporated in the fabrication process under very mild conditions to achieve self-healing properties [13,14,15,16]. Selenium-containing polymers show versatile responsive behaviors to multiple stimuli, such as oxidation, reduction, and irradiation [17,18,19,20,21,22,23], which makes them potentially useful bio-building blocks.

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