Voltage-sensitive styryl dyes as singlet oxygen targets on the surface of bilayer lipid membrane

Sokolov, V.S.; Gavril’chik, A. N.; Kulagina, A.O.; Meshkov, Ivan N.; Pohl, Peter; Gorbunova, Yulia G.

doi:10.1016/j.jphotobiol.2016.05.016

Cited by 21 publications

(23 citation statements)

References 41 publications

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“…This dye is more sensitive to changes in the dipole potential and adsorbed faster on the lipid membrane compared with RH421 and di-8-ANEPPS. 22,25 We assume that under the conditions of excessive lipid concentrations (1.3 mM) over the concentrations of the hydrophobic anions (o80 mM) COSAN analogs adsorbed completely on the surface of the lipid membrane and that the change of the electrical potential profile in the membrane related to surface potential should be equal for all derivatives. It can be suggested therefore that the variations in the fluorescence ratio for different anions (Fig.…”

Section: Resultsmentioning

confidence: 99%

Fast flip–flop of halogenated cobalt bis(dicarbollide) anion in a lipid bilayer membrane

Rokitskaya

Kosenko

Sivaev

et al. 2017

Phys. Chem. Chem. Phys.

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Transmembrane translocation (flip-flop) of cobalt bis(dicarbollide) (COSAN) anions, elicited by application of a voltage-jump across the lipid bilayer membrane, manifested itself in monoexponential electrical current transients in the microsecond time scale. Halogenation of COSAN led to multi-fold acceleration of the flip-flop, the effect increasing with the molecular weight of the halogens. The exception was a fluorinated analog which exhibited slowing of the translocation kinetics. Measurements of the fluorescence ratio of the dye di-4-ANEPPS in lipid vesicles showed significant differences in the adsorption of studied hydrophobic anions. Based on these data, it can be concluded that COSAN and COSAN-F were located on the surface of the lipid membrane in the cisoid conformation increasing the dipole potential of the lipid membrane, while other halogenated COSAN analogs were adsorbed in the transoid conformation. Differences in the flip-flop kinetics of COSAN analogs were attributed to variation in the molecular volume of the anions and their orientation on the membrane surface.

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Section: Resultsmentioning

confidence: 99%

Fast flip–flop of halogenated cobalt bis(dicarbollide) anion in a lipid bilayer membrane

Rokitskaya

Kosenko

Sivaev

et al. 2017

Phys. Chem. Chem. Phys.

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“…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%

“…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%

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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“…Bilayer lipid membares were used as models of cell surfaces for the tests of photodynamic activity of phthalocyanines using voltage-sensitive styryl dyes as singlet oxygen targets (Figure 31). [35] Photosensitizing and emission properties of P(V) porphyrins were studied. It was demonstrated that the nature of the axial ligands, occupying the apical position on the P centre adopting an octahedral coordination geometry, strongly influences singlet oxygen generation and charge transfer and allows switching between the two processes ( Figure 32).…”

Section: Photophysical and Nonlinear Optical Properties Of Tetrapyrromentioning

confidence: 99%

“…Voltage-sensitive styryl dyes as singlet oxygen targets on the surface of bilayer lipid membrane. [35] …”

Section: Photophysical and Nonlinear Optical Properties Of Tetrapyrromentioning

confidence: 99%

Advances in Tetrapyrrolic Chemistry over 2013-2017 of Research group Headed by Full Member of RAS A. Yu. Tsivadze: Highlights on the Occasion of his Anniversary

Gorbunova¹,

Martynov²,

Stuzhin³

et al. 2017

MHC

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Voltage-sensitive styryl dyes as singlet oxygen targets on the surface of bilayer lipid membrane

Cited by 21 publications

References 41 publications

Fast flip–flop of halogenated cobalt bis(dicarbollide) anion in a lipid bilayer membrane

Fast flip–flop of halogenated cobalt bis(dicarbollide) anion in a lipid bilayer membrane

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

Advances in Tetrapyrrolic Chemistry over 2013-2017 of Research group Headed by Full Member of RAS A. Yu. Tsivadze: Highlights on the Occasion of his Anniversary

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