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Thiocarbonyl Derivatives of Natural Chlorins: Synthesis Using Lawesson’s Reagent and a Study of Their Properties
The development of sulfur-containing pharmaceutical compounds is important in the advancement of medicinal chemistry. Photosensitizers (PS) that acquire new properties upon incorporation of sulfur-containing groups or individual sulfur atoms into their structure are not neglected, either. In this wo...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10222512/ https://www.ncbi.nlm.nih.gov/pubmed/37241955 http://dx.doi.org/10.3390/molecules28104215 |
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author | Pogorilyy, Viktor Ostroverkhov, Petr Efimova, Valeria Plotnikova, Ekaterina Bezborodova, Olga Diachkova, Ekaterina Vasil’ev, Yuriy Pankratov, Andrei Grin, Mikhail |
author_facet | Pogorilyy, Viktor Ostroverkhov, Petr Efimova, Valeria Plotnikova, Ekaterina Bezborodova, Olga Diachkova, Ekaterina Vasil’ev, Yuriy Pankratov, Andrei Grin, Mikhail |
author_sort | Pogorilyy, Viktor |
collection | PubMed |
description | The development of sulfur-containing pharmaceutical compounds is important in the advancement of medicinal chemistry. Photosensitizers (PS) that acquire new properties upon incorporation of sulfur-containing groups or individual sulfur atoms into their structure are not neglected, either. In this work, a synthesis of sulfur-containing derivatives of natural chlorophyll a using Lawesson’s reagent was optimized. Thiocarbonyl chlorins were shown to have a significant bathochromic shift in the absorption and fluorescence bands. The feasibility of functionalizing the thiocarbonyl group at the macrocycle periphery by formation of a Pt(II) metal complex in the chemotherapeutic agent cisplatin was shown. The chemical stability of the resulting conjugate in aqueous solution was studied, and it was found to possess a high cytotoxic activity against sarcoma S37 tumor cells that results from the combined photodynamic and chemotherapeutic effect on these cells. |
format | Online Article Text |
id | pubmed-10222512 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-102225122023-05-28 Thiocarbonyl Derivatives of Natural Chlorins: Synthesis Using Lawesson’s Reagent and a Study of Their Properties Pogorilyy, Viktor Ostroverkhov, Petr Efimova, Valeria Plotnikova, Ekaterina Bezborodova, Olga Diachkova, Ekaterina Vasil’ev, Yuriy Pankratov, Andrei Grin, Mikhail Molecules Article The development of sulfur-containing pharmaceutical compounds is important in the advancement of medicinal chemistry. Photosensitizers (PS) that acquire new properties upon incorporation of sulfur-containing groups or individual sulfur atoms into their structure are not neglected, either. In this work, a synthesis of sulfur-containing derivatives of natural chlorophyll a using Lawesson’s reagent was optimized. Thiocarbonyl chlorins were shown to have a significant bathochromic shift in the absorption and fluorescence bands. The feasibility of functionalizing the thiocarbonyl group at the macrocycle periphery by formation of a Pt(II) metal complex in the chemotherapeutic agent cisplatin was shown. The chemical stability of the resulting conjugate in aqueous solution was studied, and it was found to possess a high cytotoxic activity against sarcoma S37 tumor cells that results from the combined photodynamic and chemotherapeutic effect on these cells. MDPI 2023-05-20 /pmc/articles/PMC10222512/ /pubmed/37241955 http://dx.doi.org/10.3390/molecules28104215 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Pogorilyy, Viktor Ostroverkhov, Petr Efimova, Valeria Plotnikova, Ekaterina Bezborodova, Olga Diachkova, Ekaterina Vasil’ev, Yuriy Pankratov, Andrei Grin, Mikhail Thiocarbonyl Derivatives of Natural Chlorins: Synthesis Using Lawesson’s Reagent and a Study of Their Properties |
title | Thiocarbonyl Derivatives of Natural Chlorins: Synthesis Using Lawesson’s Reagent and a Study of Their Properties |
title_full | Thiocarbonyl Derivatives of Natural Chlorins: Synthesis Using Lawesson’s Reagent and a Study of Their Properties |
title_fullStr | Thiocarbonyl Derivatives of Natural Chlorins: Synthesis Using Lawesson’s Reagent and a Study of Their Properties |
title_full_unstemmed | Thiocarbonyl Derivatives of Natural Chlorins: Synthesis Using Lawesson’s Reagent and a Study of Their Properties |
title_short | Thiocarbonyl Derivatives of Natural Chlorins: Synthesis Using Lawesson’s Reagent and a Study of Their Properties |
title_sort | thiocarbonyl derivatives of natural chlorins: synthesis using lawesson’s reagent and a study of their properties |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10222512/ https://www.ncbi.nlm.nih.gov/pubmed/37241955 http://dx.doi.org/10.3390/molecules28104215 |
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