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Delayed release singlet oxygen sensitizers based on pyridone-appended porphyrins†
Susan Callaghan,Mikhail A. Filatov,Elisabeth Sitte,Huguette Savoie,Ross W. Boyle,Keith J. Flanagan
Photochemical & Photobiological Sciences Pub Date : 08/22/2017 00:00:00 , DOI:10.1039/C7PP00244K
Abstract

A new type of porphyrin photosensitizer capable of generating singlet oxygen upon irradiation, storing it through binding to pyridone subunits, followed by slow release at 20–40 °C, is reported. The timescale of singlet oxygen release can be varied depending on the pyridone group substitution pattern, forming endoperoxides of different stabilities. Modified tetra- and octa-substituted pyridone-porphyrins showed solubility in water, allowing for straightforward delivery into cells. The effect of delayed singlet oxygen formation due to endoperoxide decomposition was demonstrated on cancer cells in vitro.

Graphical abstract: Delayed release singlet oxygen sensitizers based on pyridone-appended porphyrins
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