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meso-Thiophenium Porphyrins and Their Zn(II) Complexes: A New Category of Cationic Photosensitizers.

ABSTRACT: A new category of cationic meso-thiophenium porphyrins are introduced as possible alternatives to the popular meso-pyridinium porphyrins. Combinations of cationic porphyrins bearing meso-2-methylthiophenium and meso-4-hydroxyphenyl moieties T₂(OH)₂M (A₂B₂ type) and T(OH)₃M (AB₃ type) along with their zinc(II) complexes T₂(OH)₂MZn and T(OH)₃MZn, are reported. The increase in the number of thienyl groups attached to the meso-positions of the porphyrin derivatives (A₂B₂ frame) has been shown to impart longer fluorescence lifetimes and stronger photocytotoxicity toward A549 lung cancer cells, as evident with T₂(OH)₂M and its corresponding diamagnetic metal complex T₂(OH)₂MZn. The photoactivated T₂(OH)₂MZn imparts an early stage reactive oxygen species (ROS) upregulation and antioxidant depletion in A549 cells and contributes to the strongest oxidative stress-induced cell death mechanism in the series. The DFT calculations of the singlet-triplet energy gap (ΔE) of all the four hydrophilic thiophenium porphyrin derivatives establish the potential applicability of these cationic photosensitizers as PDT agents.

SUBMITTER: Mazumdar ZH

PROVIDER: S-EPMC7549270 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Synthesis and in vitro PDT evaluation of new porphyrins containing meso-epoxymethylaryl cationic groups.

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| S-EPMC6693339 | biostudies-literature

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| S-EPMC7570530 | biostudies-literature

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| S-EPMC6680645 | biostudies-literature

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