Thieno[3,4-<i>d</i>]pyrimidin-4(3<i>H</i>)-thione: an effective, oxygenation independent, heavy-atom-free photosensitizer for cancer cells

Crespo‐Hernández, Carlos E.; Ortiz‐Rodríguez, Luis A.; Fang, Ye‐Guang; Niogret, Germain; Hadidi, Kaivin; Hoehn, Sean J.; Folkwein, Heather J.; Jockusch, Steffen; Tor, Yitzhak; Cui, Ganglong; Levi, Liraz

doi:10.1039/d3sc02592f

Chem. Sci.

2023

DOI: 10.1039/d3sc02592f

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Thieno[3,4-d]pyrimidin-4(3H)-thione: an effective, oxygenation independent, heavy-atom-free photosensitizer for cancer cells

Carlos E. Crespo‐Hernández

Luis A. Ortiz‐Rodríguez

Ye‐Guang Fang

et al.

Abstract: All-organic, heavy-atom-free photosensitizers based on thionation of nucleobases are receiving increased attention because they are easy to make, noncytotoxic, work both in the presence and absence of molecular oxygen, and...

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2024

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Thio and Seleno‐Psoralens as Efficient Triplet Harvesting Photosensitizers for Photodynamic Therapy

Jena,

Mohanty,

Rout Rout

et al. 2024

Chemistry A European J

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The Psoralen (Pso) molecule finds extensive applications in photo‐chemotherapy, courtesy of its triplet state forming ability. Sulfur and selenium replacement of exocyclic carbonyl oxygen of organic chromophores foster efficient triplet harvesting with near unity triplet quantum yield. These triplet‐forming photosensitizers are useful in Photodynamic Therapy (PDT) applications for selective apoptosis of cancer cells. In this work, we have critically assessed the effect of the sulfur and selenium substitution at the exocyclic carbonyl (TPso and SePso, respectively) and endocyclic oxygen positions of Psoralen. It resulted in a significant redshifted absorption spectrum to access the PDT therapeutic window with increased oscillator strength. The reduction in singlet‐triplet energy gap and enhancement in the spin‐orbit coupling values increase the number of intersystem crossing (ISC) pathways to the triplet manifold, which shortens the ISC lifetime from 10‐5 s for Pso to 10‐8 s for TPso and 10‐9 s for SePso. The intramolecular photo‐induced electron transfer process, a competitive pathway to ISC, is also considerably curbed by these exocyclic functionalizations. In addition, a maximum of 115 GM of two‐photon absorption (2PA) with IR absorption (660‐1050 nm) confirms that the Psoralen skeleton can be effectively tweaked via single chalcogen atom replacement to design a suitable PDT photosensitizer.

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Thio and Seleno‐Psoralens as Efficient Triplet Harvesting Photosensitizers for Photodynamic Therapy

Jena,

Mohanty,

Rout Rout

et al. 2024

Chemistry A European J

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Recent advances in minimal fluorescent probes for optical imaging

de Moliner,

Nadal-Bufi,

Vendrell

2024

Current Opinion in Chemical Biology

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Thieno[3,4-d]pyrimidin-4(3H)-thione: an effective, oxygenation independent, heavy-atom-free photosensitizer for cancer cells

Abstract: All-organic, heavy-atom-free photosensitizers based on thionation of nucleobases are receiving increased attention because they are easy to make, noncytotoxic, work both in the presence and absence of molecular oxygen, and...

Cited by 2 publications

References 70 publications

Thio and Seleno‐Psoralens as Efficient Triplet Harvesting Photosensitizers for Photodynamic Therapy

Thio and Seleno‐Psoralens as Efficient Triplet Harvesting Photosensitizers for Photodynamic Therapy

Recent advances in minimal fluorescent probes for optical imaging

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