4.4 Article

Pyridinium Alkynylanthracenes as Sensitizers for Photodynamic Therapy

Journal

PHOTOCHEMISTRY AND PHOTOBIOLOGY
Volume 98, Issue 1, Pages 193-201

Publisher

WILEY
DOI: 10.1111/php.13554

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Funding

  1. University of Potsdam

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Research found that the three isomeric methylpyridinium alkynylanthracenes 1op are effective sensitizers for photodynamic therapy, capable of initiating DNA strand breaks and impacting cellular integrity. Isomer 1m, which can be easily synthesized, is a promising candidate for cancer therapy.
Photodynamic therapy (PDT) is a mild but effective method to treat certain types of cancer upon irradiation with visible light. Here, three isomeric methylpyridinium alkynylanthracenes 1op were evaluated as sensitizers for PDT. Upon irradiation with blue or green light, all three compounds show the ability to initiate strand breaks of plasmid DNA. The mayor species responsible for cleavage is singlet oxygen (O-1(2)) as confirmed by scavenging reagents. Only isomers 1m and 1p can be incorporated into HeLa cells, whereas isomer 1o cannot permeate through the membrane. While isomer 1m targets the cell nucleus, isomer 1p assembles in the cellular cytoplasm and impacts the cellular integrity. This is in accordance with a moderate toxicity of 1p in the dark, whereas 1m exhibits no dark toxicity. Both isomers are suitable as PDT reagents, with a CC50 of 3 mu m and 75 nm, for 1p and 1m, respectively. Thus, derivative 1m, which can be easily synthesized, becomes an interesting candidate for cancer therapy.

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