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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...

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Autores principales: Pogorilyy, Viktor, Ostroverkhov, Petr, Efimova, Valeria, Plotnikova, Ekaterina, Bezborodova, Olga, Diachkova, Ekaterina, Vasil’ev, Yuriy, Pankratov, Andrei, Grin, Mikhail
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
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.
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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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