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Issue 39, 2018
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Phosphinatophenylporphyrins tailored for high photodynamic efficacy

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Abstract

The development of effective photosensitizers is particularly attractive for photodynamic therapy of cancer. Three novel porphyrin photosensitizers functionalized with phosphinic groups were synthesized and their physicochemical, photophysical, and photobiological properties were collected. Phosphinic acid groups (R1R2POOH) attached to the porphyrin moiety (R1) contain different R2 substituents (methyl, isopropyl, phenyl in this study). The presence of phosphinic groups does not influence absorption and photophysical properties of the porphyrin units, including the O2(1Δg) productivity. In vitro studies show that these porphyrins accumulate in cancer cells, are inherently nontoxic, however, exhibit high phototoxicity upon irradiation with visible light with their phototoxic efficacy tuned by R2 substituents on the phosphorus centre. Thus, phosphinatophenylporphyrin with isopropyl substituents has the strongest photodynamic efficacy due to the most efficient cellular uptake. We demonstrate that these porphyrins are attractive candidates for photodynamic applications since their photodynamic efficacy can be easily tuned by the R2 substituent.

Graphical abstract: Phosphinatophenylporphyrins tailored for high photodynamic efficacy

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Publication details

The article was received on 14 Aug 2018, accepted on 18 Sep 2018 and first published on 19 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB01984C
Citation: Org. Biomol. Chem., 2018,16, 7274-7281
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    Phosphinatophenylporphyrins tailored for high photodynamic efficacy

    J. Hynek, M. Koncošová, J. Zelenka, I. Křížová, T. Ruml, P. Kubát, J. Demel and K. Lang, Org. Biomol. Chem., 2018, 16, 7274
    DOI: 10.1039/C8OB01984C

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