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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Cited by 3 publications

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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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Thio and Seleno Derivatives of Angelicin as Efficient Triplet Harvesting Photosensitizers: Implications in Photodynamic Therapy

Mohanty,

Sarang,

Rout

et al. 2024

ChemPhysChem

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Photodynamic therapy (PDT) is widely accepted in medical practice for its targeted induction of apoptosis in cancerous cells. Angelicin (Ang) has traditionally been known for its efficacy in cancer treatment and its capability to enter a photoexcited triplet state. This study has comprehensively assessed the effects of substituting individual chalcogen atoms at three specific positions in Angelicin, with the objective of facilitating access to this elusive triplet state to enhance its role as a photosensitizer in PDT. The study scrutinizes various enhancements and factors that are crucial for efficient triplet harvesting. The decrease in singlet‐triplet energy gap (ΔEST) and increased spin‐orbit coupling (SOC) values present numerous viable pathways for intersystem crossing (ISC), leading to the triplet manifold. The lifetime of ISC, thus, decreases from 10−5 s−1 in Ang to 10−8 s−1 in thioangelicin (TAng) and finally to 10−9 s−1 in selenoangelicin (SeAng). Additionally, this study investigates the two‐photon absorption properties of thio and seleno‐substituted Angelicin for their potentialities as non‐UV photosensitizers. The interplay between electron‐withdrawing and electron‐donating substitutions in these derivatives significantly enhances the two‐photon absorption cross‐sections (σ) to as high as 49.3 GM while shifting the absorption wavelengths towards the infrared region enabling them as efficient PDT photosensitizers.

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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 3 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

Thio and Seleno Derivatives of Angelicin as Efficient Triplet Harvesting Photosensitizers: Implications in Photodynamic Therapy

Recent advances in minimal fluorescent probes for optical imaging

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