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Article

Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80

1
United Physicochemical Centre of Solutions, G.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences (ISC RAS), 153045 Ivanovo, Russia
2
Institute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology (ISUCT), 153012 Ivanovo, Russia
3
Institute of Chemistry of the Komi Science Centre of the Ural Branch of Russian Academy of Sciences (ICKSC UB RAS), 167000 Syktyvkar, Russia
4
Department of Biophysics, Belarussian State University (BSU), 220030 Minsk, Belarus
*
Authors to whom correspondence should be addressed.
Academic Editors: Maria Angela Castriciano, Luigi Monsù Scolaro and Andrea Romeo
Int. J. Mol. Sci. 2022, 23(10), 5294; https://doi.org/10.3390/ijms23105294
Received: 15 April 2022 / Revised: 4 May 2022 / Accepted: 6 May 2022 / Published: 10 May 2022
(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles 2.0)
Cancer and drug-resistant superinfections are common and serious problems afflicting millions worldwide. Photodynamic therapy (PDT) is a successful and clinically approved modality used for the management of many neoplastic and nonmalignant diseases. The combination of the light-activated molecules, so-called photosensitizers (PSs), with an appropriate carrier, is proved to enhance PDT efficacy both in vitro and in vivo. In this paper, we focus on the solvation of several potential chlorin PSs in the 1-octanol/phosphate saline buffer biphasic system, their interaction with non-ionic surfactant Tween 80 and photoinactivation of cancer cells. The chlorin conjugates containing d-galactose and l-arginine fragments are found to have a much stronger affinity towards a lipid-like environment compared to ionic chlorins and form molecular complexes with Tween 80 micelles in water with two modes of binding. The charged macrocyclic PSs are located in the periphery of surfactant micelles near hydrophilic head groups, whereas the d-galactose and l-arginine conjugates are deeper incorporated into the micelle structure occupying positions around the first carbon atoms of the hydrophobic surfactant residue. Our results indicate that both PSs have a pronounced affinity toward the lipid-like environment, leading to their preferential binding to low-density lipoproteins. This and the conjugation of chlorin e6 with the tumor-targeting molecules are found to enhance their accumulation in cancer cells and PDT efficacy. View Full-Text
Keywords: photodynamic therapy; chlorin photosensitizers; 1-octanol/phosphate saline buffer partition; solvation; singlet oxygen generation; photoinactivation; interaction with Tween 80 photodynamic therapy; chlorin photosensitizers; 1-octanol/phosphate saline buffer partition; solvation; singlet oxygen generation; photoinactivation; interaction with Tween 80
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MDPI and ACS Style

Kustov, A.V.; Morshnev, P.K.; Kukushkina, N.V.; Smirnova, N.L.; Berezin, D.B.; Karimov, D.R.; Shukhto, O.V.; Kustova, T.V.; Belykh, D.V.; Mal’shakova, M.V.; Zorin, V.P.; Zorina, T.E. Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80. Int. J. Mol. Sci. 2022, 23, 5294. https://doi.org/10.3390/ijms23105294

AMA Style

Kustov AV, Morshnev PK, Kukushkina NV, Smirnova NL, Berezin DB, Karimov DR, Shukhto OV, Kustova TV, Belykh DV, Mal’shakova MV, Zorin VP, Zorina TE. Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80. International Journal of Molecular Sciences. 2022; 23(10):5294. https://doi.org/10.3390/ijms23105294

Chicago/Turabian Style

Kustov, Andrey V., Philipp K. Morshnev, Natal’ya V. Kukushkina, Nataliya L. Smirnova, Dmitry B. Berezin, Dmitry R. Karimov, Olga V. Shukhto, Tatyana V. Kustova, Dmitry V. Belykh, Marina V. Mal’shakova, Vladimir P. Zorin, and Tatyana E. Zorina. 2022. "Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80" International Journal of Molecular Sciences 23, no. 10: 5294. https://doi.org/10.3390/ijms23105294

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