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月 2022
Accepted
22 4月 2022
First published
23 4月 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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