Issue 20, 2022

A host–guest strategy for converting the photodynamic agents from a singlet oxygen generator to a superoxide radical generator

Abstract

Type-I photosensitizers (PSs) generate cytotoxic oxygen radicals by electron transfer even in a hypoxic environment. Nevertheless, the preparation of type-I PSs remains a challenge due to the competition of triplet–triplet energy transfer with O2 (type-II process). In this work, we report an effective strategy for converting the conventional type-II PS to a type-I PS by host–guest complexation. Electron-rich pillar[5]arenes are used as an electron donor and macrocyclic host to produce a host–guest complex with the traditional electron-deficient type-II PS, an iodide BODIPY-based guest. The host–guest complexation promotes intermolecular electron transfer from the pillar[5]arene moiety to BODIPY and then to O2 by the type-I process upon light-irradiation, leading to efficient generation of the superoxide radical (O2˙). The results of anti-tumor studies indicate that this supramolecular PS demonstrates high photodynamic therapy efficacy even under hypoxic conditions. This work provides an efficient method to prepare type-I PSs from existing type-II PSs by using a supramolecular strategy.

Graphical abstract: A host–guest strategy for converting the photodynamic agents from a singlet oxygen generator to a superoxide radical generator

Supplementary files

Article information

Article type
Edge Article
Submitted
14 3 2022
Accepted
22 4 2022
First published
23 4 2022
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., 2022,13, 5951-5956

A host–guest strategy for converting the photodynamic agents from a singlet oxygen generator to a superoxide radical generator

K. Teng, L. Niu and Q. Yang, Chem. Sci., 2022, 13, 5951 DOI: 10.1039/D2SC01469F

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