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Curcuminoid Chalcones: Synthesis, Stability, and New Neuroprotective and Sonosensitising Activities

The primary purpose of this work was to design and obtain a series of curcuminoid chalcone–NSAID hybrid derivatives. The ester-type hybrid compounds with ibuprofen (i), ketoprofen (ii), and naproxen (iii) were obtained in two ways, using the Claisen–Schmidt reaction and the Steglich esterification r...

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Autores principales: Olender, Dorota, Józkowiak, Małgorzata, Piotrowska-Kempisty, Hanna, Sowa-Kasprzak, Katarzyna, Zaprutko, Lucjusz, Muszalska-Kolos, Izabela, Baranowska-Wójcik, Ewa, Szwajgier, Dominik
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10535624/
https://www.ncbi.nlm.nih.gov/pubmed/37765139
http://dx.doi.org/10.3390/ph16091331
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author Olender, Dorota
Józkowiak, Małgorzata
Piotrowska-Kempisty, Hanna
Sowa-Kasprzak, Katarzyna
Zaprutko, Lucjusz
Muszalska-Kolos, Izabela
Baranowska-Wójcik, Ewa
Szwajgier, Dominik
author_facet Olender, Dorota
Józkowiak, Małgorzata
Piotrowska-Kempisty, Hanna
Sowa-Kasprzak, Katarzyna
Zaprutko, Lucjusz
Muszalska-Kolos, Izabela
Baranowska-Wójcik, Ewa
Szwajgier, Dominik
author_sort Olender, Dorota
collection PubMed
description The primary purpose of this work was to design and obtain a series of curcuminoid chalcone–NSAID hybrid derivatives. The ester-type hybrid compounds with ibuprofen (i), ketoprofen (ii), and naproxen (iii) were obtained in two ways, using the Claisen–Schmidt reaction and the Steglich esterification reaction. The designed molecules were successfully synthesised, and FT-IR, MS, and NMR spectroscopy confirmed their structures. Moreover, the cytotoxic effect of the sonodynamic therapy and the anti-inflammatory, antioxidant, and anticholinergic properties of some curcuminoid chalcones and curcuminoid chalcones hybrids were evaluated. The curcuminoid chalcone derivatives showed promising neuroprotective activity as sonosensitisers for sonodynamic therapy in the studied cell lines. Additionally, the stability of the ester-type hybrid compounds with promising activity was determined. The RP-HPLC method was used to observe the degradation of the tested compounds. Studies have shown that structural isomers of ester-type hybrid compounds (3ai, 3bi) are characterised by a similar susceptibility to degradation factors, i.e., they are extremely unstable in alkaline environments, very unstable in acidic environments, unstable in neutral environments, practically stable in oxidising environments, and photolabile in solutions and in the solid phase. These compounds maintain adequate stability in environment at pH 1.2 and 6.8, which may make them good candidates for developing formulations for oral administration.
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spelling pubmed-105356242023-09-29 Curcuminoid Chalcones: Synthesis, Stability, and New Neuroprotective and Sonosensitising Activities Olender, Dorota Józkowiak, Małgorzata Piotrowska-Kempisty, Hanna Sowa-Kasprzak, Katarzyna Zaprutko, Lucjusz Muszalska-Kolos, Izabela Baranowska-Wójcik, Ewa Szwajgier, Dominik Pharmaceuticals (Basel) Article The primary purpose of this work was to design and obtain a series of curcuminoid chalcone–NSAID hybrid derivatives. The ester-type hybrid compounds with ibuprofen (i), ketoprofen (ii), and naproxen (iii) were obtained in two ways, using the Claisen–Schmidt reaction and the Steglich esterification reaction. The designed molecules were successfully synthesised, and FT-IR, MS, and NMR spectroscopy confirmed their structures. Moreover, the cytotoxic effect of the sonodynamic therapy and the anti-inflammatory, antioxidant, and anticholinergic properties of some curcuminoid chalcones and curcuminoid chalcones hybrids were evaluated. The curcuminoid chalcone derivatives showed promising neuroprotective activity as sonosensitisers for sonodynamic therapy in the studied cell lines. Additionally, the stability of the ester-type hybrid compounds with promising activity was determined. The RP-HPLC method was used to observe the degradation of the tested compounds. Studies have shown that structural isomers of ester-type hybrid compounds (3ai, 3bi) are characterised by a similar susceptibility to degradation factors, i.e., they are extremely unstable in alkaline environments, very unstable in acidic environments, unstable in neutral environments, practically stable in oxidising environments, and photolabile in solutions and in the solid phase. These compounds maintain adequate stability in environment at pH 1.2 and 6.8, which may make them good candidates for developing formulations for oral administration. MDPI 2023-09-21 /pmc/articles/PMC10535624/ /pubmed/37765139 http://dx.doi.org/10.3390/ph16091331 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
Olender, Dorota
Józkowiak, Małgorzata
Piotrowska-Kempisty, Hanna
Sowa-Kasprzak, Katarzyna
Zaprutko, Lucjusz
Muszalska-Kolos, Izabela
Baranowska-Wójcik, Ewa
Szwajgier, Dominik
Curcuminoid Chalcones: Synthesis, Stability, and New Neuroprotective and Sonosensitising Activities
title Curcuminoid Chalcones: Synthesis, Stability, and New Neuroprotective and Sonosensitising Activities
title_full Curcuminoid Chalcones: Synthesis, Stability, and New Neuroprotective and Sonosensitising Activities
title_fullStr Curcuminoid Chalcones: Synthesis, Stability, and New Neuroprotective and Sonosensitising Activities
title_full_unstemmed Curcuminoid Chalcones: Synthesis, Stability, and New Neuroprotective and Sonosensitising Activities
title_short Curcuminoid Chalcones: Synthesis, Stability, and New Neuroprotective and Sonosensitising Activities
title_sort curcuminoid chalcones: synthesis, stability, and new neuroprotective and sonosensitising activities
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10535624/
https://www.ncbi.nlm.nih.gov/pubmed/37765139
http://dx.doi.org/10.3390/ph16091331
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