Peripheral RAFT Polymerization on a Covalent Organic Polymer with Enhanced Aqueous Compatibility for Controlled Generation of Singlet Oxygen

Haiwang Lai; Jieyu Yan; Shan Liu; Qizhi Yang; Feiyue Xing; Pu Xiao

doi:10.1002/anie.202002446

Peripheral RAFT Polymerization on a Covalent Organic Polymer with Enhanced Aqueous Compatibility for Controlled Generation of Singlet Oxygen

Angew Chem Int Ed Engl. 2020 Jun 22;59(26):10431-10435. doi: 10.1002/anie.202002446. Epub 2020 Apr 8.

Authors

Haiwang Lai^{1

2}, Jieyu Yan¹, Shan Liu¹, Qizhi Yang¹, Feiyue Xing^{1

3}, Pu Xiao²

Affiliations

¹ Department of Immunobiology, College of Life Science and Technology, Jinan University, 601 Huangpu West Avenue, Guangzhou, 510632, China.
² Research School of Chemistry, The Australian National University, Canberra, ACT, 2601, Australia.
³ MOE Key Laboratory of Tumor Molecular Biology, Jinan University, Guangzhou, 510632, China.

PMID: 32196858
DOI: 10.1002/anie.202002446

Abstract

A covalent organic polymer (COP) is prepared by crosslinking the photosensitizer 4,4',4'',4'''-(porphyrin-5,10,15,20-tetrayl)tetraaniline (TAPP) with 4,4'-(anthracene-9,10-diyl)dibenzoic acid (ADDA) via 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide/4-dimethylaminopyridine coupling. The COP is further modified with a hydrophilic polymer, poly(poly(ethylene glycol) methyl ether methacrylate) by grafting-from reversible-addition-fragmentation chain transfer (RAFT) polymerization to enhance its solubility in various solvents. The modified COP can bind singlet oxygen through the formation of endoperoxide by ADDA upon the exposure to red light irradiation. Singlet oxygen can be then released via the photodynamic mechanism or the cycloreversion by endoperoxide when heated at 110 °C. These results open new possibilities for simultaneous generation of singlet oxygen by the photodynamic route and singlet oxygen carriers, demonstrating promise for treating hypoxic tumors.

Keywords: covalent organic polymers; endoperoxides; grafting-from; photodynamic mechanism; singlet oxygen.

Publication types

Research Support, Non-U.S. Gov't