Tuning singlet oxygen generation with caged organic photosensitizers

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.

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Publication Details

Journal
Nature Communications
Published
2024-09-03
DOI
https://doi.org/10.1038/s41467-024-51872-y
Citations
23
Primary Topic
Photochromic and Fluorescence Chemistry
Type
article
Field-Weighted Citation Impact
2.69

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article

Tuning singlet oxygen generation with caged organic photosensitizers

Deborah Seah, Kostiantyn Kozoriz, Larissa Maierhofer, Asier Unciti‐Broceta et al.
23 citations
Nature Communications
Photochromic and Fluorescence Chemistry
2.69
article

Tuning singlet oxygen generation with caged organic photosensitizers

Deborah Seah, Kostiantyn Kozoriz, Larissa Maierhofer, Asier Unciti‐Broceta, Fabio De Moliner, Marc Vendrell, Catherine Adam, M. Carmen Ortega‐Liebana, Sam Benson, Ferran Nadal‐Bufí, Eleni Nestoros, Jun‐Seok Lee, Zhiming Cheng
article en
23 citations

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.

Nature CommunicationsVol. 15(1)
Universidad de Granada (ES), Korea University (KR), Edinburgh Cancer Research (GB), MRC Centre for Regenerative Medicine (GB), Pfizer-University of Granada-Junta de Andalucía Centre for Genomics and Oncological Research (ES), Centre for Inflammation Research (GB), University of Edinburgh (GB)
European Commission, Horizon 2020 Framework Programme, Medical Research Council, Engineering and Physical Sciences Research Council
Openalex Percentile: Top 6%
Photochromic and Fluorescence Chemistry
2.69
DOIOpen Access PDFOpenAlex
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