Phosphinatophenylporphyrins tailored for high photodynamic efficacy

0494406 - ÚACH 2019 RIV GB eng J - Journal Article
Hynek, Jan - Koncošová, M. - Zelenka, J. - Křížová, I. - Ruml, T. - Kubát, Pavel - Demel, Jan - Lang, Kamil
Phosphinatophenylporphyrins tailored for high photodynamic efficacy.
Organic & Biomolecular Chemistry. Roč. 16, č. 39 (2018), s. 7274-7281. ISSN 1477-0520. E-ISSN 1477-0539
R&D Projects: GA ČR(CZ) GA16-15020S; GA ČR(CZ) GA16-02098S
Institutional support: RVO:61388980 ; RVO:61388955
Keywords : phosphinic acid groups * singlet oxygent * porphyrins * therapy
OECD category: Inorganic and nuclear chemistry; Physical chemistry (UFCH-W)
Impact factor: 3.490, year: 2018

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 ((RRPOOH)-R-1-P-2) attached to the porphyrin moiety (R-1) contain different R-2 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 O-2((1)Delta(g)) 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 R-2 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 R-2 substituent.
Permanent Link: http://hdl.handle.net/11104/0288315


Research data: RSC publishing