Adsorption and photodynamic efficiency of meso-tetrakis(p-sulfonatophenyl)porphyrin on the surface of bilayer lipid membranes

Konstantinova, A.N.; Sokolov, V.S.; Jiménez-Munguía, Irene; Finogenova, O.A.; Ermakov, Yu. A.; Gorbunova, Yulia G.

doi:10.1016/j.jphotobiol.2018.10.001

Cited by 12 publications

(14 citation statements)

References 30 publications

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“…The values of ζ-potentials were equal or slightly lower than the ∆ϕ b values, indicating the absence or shallow insertion of the charged groups of the porphyrin molecules into the lipid membrane [34,35]. The same behavior was observed earlier for the negatively charged porphyrins [19]. The difference in ∆ϕ b for three porphyrins can be explained by affinity of these compounds to the lipid bilayer.…”

Section: Adsorption On the Membranesupporting

confidence: 70%

“…The setup for electrical measurements was similar to that described by us earlier [18,19]. Measurements were performed with the aid of a pair of Ag/AgCl electrodes with agar bridges.…”

Section: Experiments At Blmmentioning

confidence: 99%

“…where g 0 and g are the conductance before and after the addition of porphyrins, respectively; z = +1 is the charge number of the nonactin-K + complex; and F, R and T are the Faraday number, gas constant and absolute temperature, respectively. To estimate the surface concentration of porphyrin molecules at the membrane, we determined the change of the membrane surface charge caused by their adsorption, using the Gouy-Chapman equation relating the membrane surface potential to its surface charge density [19,20]. The change in membrane surface potential (ζ-potential) upon adsorption of porphyrins was measured via electrophoretic mobility of liposomes by dynamic light scattering using a Zetasizer II (Malvern Instruments, Malvern, UK) supplied with a correlator (PhotoCor SP, College Park, MD, USA).…”

Section: Experiments At Blmmentioning

confidence: 99%

“…This indicates that the difference in the efficiency for three porphyrins could correlate with their affinity to BLM. To prove this hypothesis we calculated the surface charge density for adsorbed porphyrin molecules using ζ-potential data and the Gouy-Chapman equation [19].…”

Section: Photodynamic Efficiencymentioning

confidence: 99%

“…Recently, we have developed a new approach for the investigation of the efficiency of PSs on BLM based on measurements of boundary potentials at the membrane/water interface [17,18]. Using this approach, we have studied sulfonate-substituted aluminum phthalocyanine and 5,10,15,20tetrakis(p-sulfonatophenyl)porphyrin as photosensitizers [18][19][20] and have revealed several problems decreasing the efficiency of PSs, namely, the quenching of SO by phthalocyanines in the membrane [13,20] and weak binding of 5,10,15,20-tetrakis(p-sulfonatophenyl)porphyrin (TPPS4) to the BLM at low pH due to aggregation [19]. In this regard, porphyrins with positively charged peripheral groups seem to be the most promising molecules for PDT [21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2019

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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.

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Section: Adsorption On the Membranesupporting

confidence: 70%

“…The setup for electrical measurements was similar to that described by us earlier [18,19]. Measurements were performed with the aid of a pair of Ag/AgCl electrodes with agar bridges.…”

Section: Experiments At Blmmentioning

confidence: 99%

Section: Experiments At Blmmentioning

confidence: 99%

Section: Photodynamic Efficiencymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2019

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Supramolecular assemblies based on crown- and phosphoryl-substituted phthalocyanines and their metal complexes in microheterogeneous media

et al. 2020

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The review is concerned with studies on peculiar features of supramolecular organization of phthalocyanines (Pc) bearing complex-forming substituents (15-crown-5, 2-oxyphenylphosphonic acid residues) in organized aqueous microheterogeneous media based on cationic and anionic surfactants, bile salts (BS) including sodium deoxycholate (SDC), as well as polyelectrolytes and amphiphilic polymers including a phosphate buff er (рН 7.4). Organized, SDC-based fl uorescence-active phthalocyanine-containing hydrogels obtained for the fi rst time are also considered. In vitro accumulation and localization of Pc in human cervical adenocarcinoma cells, HeLa, as well as the photochemical and sensitizing properties of Pc including light cytotoxicity and photoinduced generation of reactive oxygen species were demonstrated taking octa-crown-substituted magnesium phthalocyaninate as an example.

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Lipid monolayer as a simple model membrane for comparative assessment of the photodynamic therapy photosensitizer efficiency via macroscopic measurements

Shokurov

Novak

Ostroverkhov

et al. 2020

Journal of Photochemistry and Photobiology B: Biology

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Adsorption and photodynamic efficiency of meso-tetrakis(p-sulfonatophenyl)porphyrin on the surface of bilayer lipid membranes

Cited by 12 publications

References 30 publications

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

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

Supramolecular assemblies based on crown- and phosphoryl-substituted phthalocyanines and their metal complexes in microheterogeneous media

Lipid monolayer as a simple model membrane for comparative assessment of the photodynamic therapy photosensitizer efficiency via macroscopic measurements

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