Tuning singlet oxygen generation with caged organic photosensitizers

Eleni Nestoros, Fabio Moliner, Ferran Nadal-Bufi, Deborah Seah, M. Carmen Ortega-Liebana, Zhiming Cheng, Sam Benson, Catherine Adam, Larissa Maierhofer, Kostiantyn Kozoriz, Jun-Seok Lee, Asier Unciti-Broceta () and Marc Vendrell ()
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Eleni Nestoros: The University of Edinburgh
Fabio Moliner: The University of Edinburgh
Ferran Nadal-Bufi: The University of Edinburgh
Deborah Seah: The University of Edinburgh
M. Carmen Ortega-Liebana: University of Edinburgh
Zhiming Cheng: The University of Edinburgh
Sam Benson: The University of Edinburgh
Catherine Adam: University of Edinburgh
Larissa Maierhofer: The University of Edinburgh
Kostiantyn Kozoriz: College of Medicine, Korea University
Jun-Seok Lee: College of Medicine, Korea University
Asier Unciti-Broceta: University of Edinburgh
Marc Vendrell: The University of Edinburgh

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Controlling the succession of chemical processes with high specificity in complex systems is advantageous for widespread applications, from biomedical research to drug manufacturing. Despite synthetic advances in bioorthogonal and photochemical methodologies, there is a need for generic chemical approaches that can universally modulate photodynamic reactivity in organic photosensitizers. Herein we present a strategy to fine-tune the production of singlet oxygen in multiple photosensitive scaffolds under the activation of bioresponsive and bioorthogonal stimuli. We demonstrate that the photocatalytic activity of nitrobenzoselenadiazoles can be fully blocked by site-selective incorporation of electron-withdrawing carbamate moieties and restored on demand upon uncaging with a wide range of molecular triggers, including abiotic transition-metal catalysts. We also prove that this strategy can be expanded to most photosensitizers, including diverse structures and spectral properties. Finally, we show that such advanced control of singlet oxygen generation can be broadly applied to the photodynamic ablation of human cells as well as to regulate the release of singlet oxygen in the semi-synthesis of natural product drugs.

Date: 2024
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DOI: 10.1038/s41467-024-51872-y

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