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

Autor: Jena S; School of Chemical Sciences, National Institute of Science Education and Research (NISER), PO- Bhimpur-Padanpur Via-Jatni, District- Khurda, PIN - 752050, Bhubaneswar, India.; Homi Bhabha National Institute, Training School Complex, Anushakti Nagar, Mumbai 400094, India., Mohanty P; School of Chemical Sciences, National Institute of Science Education and Research (NISER), PO- Bhimpur-Padanpur Via-Jatni, District- Khurda, PIN - 752050, Bhubaneswar, India.; Homi Bhabha National Institute, Training School Complex, Anushakti Nagar, Mumbai 400094, India., Rout Rout S; School of Chemical Sciences, National Institute of Science Education and Research (NISER), PO- Bhimpur-Padanpur Via-Jatni, District- Khurda, PIN - 752050, Bhubaneswar, India.; Homi Bhabha National Institute, Training School Complex, Anushakti Nagar, Mumbai 400094, India., Kumar Pati S; School of Chemical Sciences, National Institute of Science Education and Research (NISER), PO- Bhimpur-Padanpur Via-Jatni, District- Khurda, PIN - 752050, Bhubaneswar, India.; Homi Bhabha National Institute, Training School Complex, Anushakti Nagar, Mumbai 400094, India., Biswal HS; School of Chemical Sciences, National Institute of Science Education and Research (NISER), PO- Bhimpur-Padanpur Via-Jatni, District- Khurda, PIN - 752050, Bhubaneswar, India.; Homi Bhabha National Institute, Training School Complex, Anushakti Nagar, Mumbai 400094, India.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Jul 11; Vol. 30 (39), pp. e202400733. Date of Electronic Publication: 2024 Jun 04.
DOI: 10.1002/chem.202400733
Abstrakt: 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 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.
(© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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