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

Autor: 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., Sarang 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., 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., 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: Chemphyschem : a European journal of chemical physics and physical chemistry [Chemphyschem] 2024 Dec 16; Vol. 25 (24), pp. e202400636. Date of Electronic Publication: 2024 Nov 04.
DOI: 10.1002/cphc.202400636
Abstrakt: 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 (ΔE ST ) 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.
(© 2024 The Authors. ChemPhysChem published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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