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Open AccessArticle

Lipid Membrane Adsorption Determines Photodynamic Efficiency of β-Imidazolyl-Substituted Porphyrins

1
National University of Science and Technology “MISiS”, 4 Leninskiy pr. 119049 Moscow, Russia
2
A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31/4 Leninskiy pr. 119071 Moscow, Russia
3
Moscow Institute of Physics and Technology, 9 Institutskiy Lane, Dolgoprudniy, 141700 Moscow Region, Russia
4
N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninskiy pr. 119119 Moscow, Russia
*
Authors to whom correspondence should be addressed.
Biomolecules 2019, 9(12), 853; https://doi.org/10.3390/biom9120853
Received: 18 November 2019 / Revised: 4 December 2019 / Accepted: 7 December 2019 / Published: 10 December 2019
Photosensitizers (PSs) represent a group of molecules capable of generating reactive oxygen species (ROS), such as singlet oxygen (SO); thus, they are considered to be promising agents for anti-cancer therapy. The enhancement of the photodynamic efficiency of these compounds requires increasing the PS activity in the cancer cell milieu and exactly at the target cells. In the present work, we report the synthesis, lipid membrane binding and photodynamic activity of three novel cationic PSs based on β-imidazolyl-substituted porphyrin and its Zn(II) and In(III) complexes (1H2, 1Zn and 1In). Comparison of the behavior of the investigated porphyrins at the bilayer lipid membrane (BLM) demonstrated the highest adsorption for the 1In complex and the lowest one for 1Zn. The photodynamic efficiency of these porphyrins was evaluated by determining the oxidation rate of the styryl dye, di-4-ANEPPS, incorporated into the lipid membrane. These rates were proportional to the surface density (SD) of the porphyrin molecules at the BLM and were roughly the same for all three porphyrins. This indicates that the adsorption of these porphyrins at the BLM determines their photodynamic efficiency rather than the extinction or quantum yield of singlet oxygen. View Full-Text
Keywords: photosensitizers; porphyrins; lipid membrane; adsorption; singlet oxygen; styryl dyes photosensitizers; porphyrins; lipid membrane; adsorption; singlet oxygen; styryl dyes
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Jiménez-Munguía, I.; Fedorov, A.K.; Abdulaeva, I.A.; Birin, K.P.; Ermakov, Y.A.; Batishchev, O.V.; Gorbunova, Y.G.; Sokolov, V.S. Lipid Membrane Adsorption Determines Photodynamic Efficiency of β-Imidazolyl-Substituted Porphyrins. Biomolecules 2019, 9, 853.

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