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Site-selected thionated benzothioxanthene chromophores as heavy-atom-free small-molecule photosensitizers for photodynamic therapy
Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.ORCID iD: 0000-0002-7815-4494
Univ Angers, CNRS, MOLTECH-ANJOU, SFR MATRIX, Angers, France.
Univ Angers, CNRS, MOLTECH-ANJOU, SFR MATRIX, Angers, France.
Univ Angers, CNRS, MOLTECH-ANJOU, SFR MATRIX, Angers, France.
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2022 (English)In: Communications Chemistry, E-ISSN 2399-3669, Vol. 5, article id 142Article in journal (Refereed) Published
Abstract [en]

Photodynamic therapy is a clinically approved anticancer modality that employs a light-activated agent (photosensitizer) to generate cytotoxic reactive oxygen species (ROS). There is therefore a growing interest for developing innovative photosensitizing agents with enhanced phototherapeutic performances. Herein, we report on a rational design synthetic procedure that converts the ultrabright benzothioxanthene imide (BTI) dye into three heavy-atom-free thionated compounds featuring close-to-unit singlet oxygen quantum yields. In contrast to the BTI, these thionated analogs display an almost fully quenched fluorescence emission, in agreement with the formation of highly populated triplet states. Indeed, the sequential thionation on the BTI scaffold induces torsion of its skeleton reducing the singlet-triplet energy gaps and enhancing the spin-orbit coupling. These potential PSs show potent cancer-cell ablation under light irradiation while remaining non-toxic under dark condition owing to a photo-cytotoxic mechanism that we believe simultaneously involves singlet oxygen and superoxide species, which could be both characterized in vitro. Our study demonstrates that this simple site-selected thionated platform is an effective strategy to convert conventional carbonyl-containing fluorophores into phototherapeutic agents for anticancer PDT.

Place, publisher, year, edition, pages
Springer Nature, 2022. Vol. 5, article id 142
National Category
Biophysics
Identifiers
URN: urn:nbn:se:umu:diva-200995DOI: 10.1038/s42004-022-00752-xISI: 000876981400002Scopus ID: 2-s2.0-85140992916OAI: oai:DiVA.org:umu-200995DiVA, id: diva2:1711476
Funder
Swedish Cancer Society, 21 0302 PT 01 HSwedish Cancer Society, 2019/126Swedish Research Council, 2021-02468EU, Horizon 2020, 722651
Note

We acknowledge the Biochemical Imaging Center at Umeå University and the National Microscopy Infrastructure, NMI (VR-RFI 2019-00217) for providing assistance in microscopy.

Available from: 2022-11-17 Created: 2022-11-17 Last updated: 2022-11-17Bibliographically approved

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Deiana, MarcoSabouri, Nasim

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