RT Journal Article
T1 Site-selected thionated benzothioxanthene chromophores as heavy-atom-free small-molecule photosensitizers for photodynamic therapy
A1 Deiana, Marco
A1 Josse, Pierre
A1 Dalinot, Clément
A1 Osmolovskyi, Artem
A1 Simón Marqués, Pablo
A1 Andrés Castán, José María
A1 Abad Galán, Laura
A1 Allain, Magali
A1 Khrouz, Lhoussain
A1 Maury, Olivier
A1 Le Bahers, Tangui
A1 Blanchard, Philippe
A1 Dabos-Seignon, Sylvie
A1 Monnereau, Cyrille
A1 Sabouri, Nasim
A1 Cabanetos, Clément
AB 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.
PB Springer Nature
SN 2399-3669
YR 2022
FD 2022
LK https://hdl.handle.net/20.500.14352/92076
UL https://hdl.handle.net/20.500.14352/92076
LA eng
NO Deiana, Marco, et al. «Site-Selected Thionated Benzothioxanthene Chromophores as Heavy-Atom-Free Small-Molecule Photosensitizers for Photodynamic Therapy». Communications Chemistry, vol. 5, n.o 1, octubre de 2022, p. 142. https://doi.org/10.1038/s42004-022-00752-x.
NO Umea University (Suecia)
DS Docta Complutense
RD 16 abr 2025