Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80
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,...
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| Format: | Article |
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2022-05-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/23/10/5294 |
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| author | Andrey V. Kustov 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 Tatyana E. Zorina |
| author_facet | Andrey V. Kustov 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 Tatyana E. Zorina |
| author_sort | Andrey V. Kustov |
| collection | DOAJ |
| description | 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 <i><span style="font-variant: small-caps;">d</span></i><i>-</i>galactose and <i><span style="font-variant: small-caps;">l</span></i>-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 <i><span style="font-variant: small-caps;">d</span></i>-galactose and <i><span style="font-variant: small-caps;">l</span></i>-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 e<sub>6</sub> with the tumor-targeting molecules are found to enhance their accumulation in cancer cells and PDT efficacy. |
| first_indexed | 2024-03-10T03:46:47Z |
| format | Article |
| id | doaj.art-d54c732d0ed6497696f295551a492f47 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T03:46:47Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
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| series | International Journal of Molecular Sciences |
| spelling | doaj.art-d54c732d0ed6497696f295551a492f472023-11-23T11:20:20ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-05-012310529410.3390/ijms23105294Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80Andrey V. Kustov0Philipp K. Morshnev1Natal’ya V. Kukushkina2Nataliya L. Smirnova3Dmitry B. Berezin4Dmitry R. Karimov5Olga V. Shukhto6Tatyana V. Kustova7Dmitry V. Belykh8Marina V. Mal’shakova9Vladimir P. Zorin10Tatyana E. Zorina11United Physicochemical Centre of Solutions, G.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences (ISC RAS), 153045 Ivanovo, RussiaUnited Physicochemical Centre of Solutions, G.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences (ISC RAS), 153045 Ivanovo, RussiaUnited Physicochemical Centre of Solutions, G.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences (ISC RAS), 153045 Ivanovo, RussiaUnited Physicochemical Centre of Solutions, G.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences (ISC RAS), 153045 Ivanovo, RussiaInstitute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology (ISUCT), 153012 Ivanovo, RussiaInstitute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology (ISUCT), 153012 Ivanovo, RussiaInstitute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology (ISUCT), 153012 Ivanovo, RussiaInstitute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology (ISUCT), 153012 Ivanovo, RussiaInstitute of Chemistry of the Komi Science Centre of the Ural Branch of Russian Academy of Sciences (ICKSC UB RAS), 167000 Syktyvkar, RussiaInstitute of Chemistry of the Komi Science Centre of the Ural Branch of Russian Academy of Sciences (ICKSC UB RAS), 167000 Syktyvkar, RussiaDepartment of Biophysics, Belarussian State University (BSU), 220030 Minsk, BelarusDepartment of Biophysics, Belarussian State University (BSU), 220030 Minsk, BelarusCancer 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 <i><span style="font-variant: small-caps;">d</span></i><i>-</i>galactose and <i><span style="font-variant: small-caps;">l</span></i>-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 <i><span style="font-variant: small-caps;">d</span></i>-galactose and <i><span style="font-variant: small-caps;">l</span></i>-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 e<sub>6</sub> with the tumor-targeting molecules are found to enhance their accumulation in cancer cells and PDT efficacy.https://www.mdpi.com/1422-0067/23/10/5294photodynamic therapychlorin photosensitizers1-octanol/phosphate saline buffer partitionsolvationsinglet oxygen generationphotoinactivation |
| spellingShingle | Andrey V. Kustov 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 Tatyana E. Zorina 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 photodynamic therapy chlorin photosensitizers 1-octanol/phosphate saline buffer partition solvation singlet oxygen generation photoinactivation |
| title | Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80 |
| title_full | Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80 |
| title_fullStr | Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80 |
| title_full_unstemmed | Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80 |
| title_short | Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80 |
| title_sort | solvation cancer cell photoinactivation and the interaction of chlorin photosensitizers with a potential passive carrier non ionic surfactant tween 80 |
| topic | photodynamic therapy chlorin photosensitizers 1-octanol/phosphate saline buffer partition solvation singlet oxygen generation photoinactivation |
| url | https://www.mdpi.com/1422-0067/23/10/5294 |
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