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17-β-Estradiol—β-Cyclodextrin Complex as Solid: Synthesis, Structural and Physicochemical Characterization
17-β-estradiol (EST) is the most potent form of naturally occurring estrogens; therefore, it has found a wide pharmaceutical application. The major problem associated with the use of EST is its very low water solubility, resulting in poor oral bioavailability. To overcome this drawback, a complexati...
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/PMC10180119/ https://www.ncbi.nlm.nih.gov/pubmed/37175157 http://dx.doi.org/10.3390/molecules28093747 |
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author | Mazurek, Anna Helena Szeleszczuk, Łukasz Bethanis, Kostas Christoforides, Elias Dudek, Marta Katarzyna Zielińska-Pisklak, Monika Pisklak, Dariusz Maciej |
author_facet | Mazurek, Anna Helena Szeleszczuk, Łukasz Bethanis, Kostas Christoforides, Elias Dudek, Marta Katarzyna Zielińska-Pisklak, Monika Pisklak, Dariusz Maciej |
author_sort | Mazurek, Anna Helena |
collection | PubMed |
description | 17-β-estradiol (EST) is the most potent form of naturally occurring estrogens; therefore, it has found a wide pharmaceutical application. The major problem associated with the use of EST is its very low water solubility, resulting in poor oral bioavailability. To overcome this drawback, a complexation with cyclodextrins (CD) has been suggested as a solution. In this work, the host–guest inclusion complex between the ß-CD and EST has been prepared using four different methods. The obtained samples have been deeply characterized using (13)C CP MAS solid state NMR, PXRD, FT-IR, TGA, DSC, and SEM. Using SCXRD, the crystal structure of the complex has been determined, being to the best of our knowledge the first solved crystal structure of an estrogen/CD complex. The periodic DFT calculations of NMR properties using GIPAW were found to be particularly helpful in the analysis of disorder in the solid state and interpretation of experimental NMR results. This work highlights the importance of a combined ssNMR/SCXRD approach to studying the structure of the inclusion complexes formed by cyclodextrins. |
format | Online Article Text |
id | pubmed-10180119 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-101801192023-05-13 17-β-Estradiol—β-Cyclodextrin Complex as Solid: Synthesis, Structural and Physicochemical Characterization Mazurek, Anna Helena Szeleszczuk, Łukasz Bethanis, Kostas Christoforides, Elias Dudek, Marta Katarzyna Zielińska-Pisklak, Monika Pisklak, Dariusz Maciej Molecules Article 17-β-estradiol (EST) is the most potent form of naturally occurring estrogens; therefore, it has found a wide pharmaceutical application. The major problem associated with the use of EST is its very low water solubility, resulting in poor oral bioavailability. To overcome this drawback, a complexation with cyclodextrins (CD) has been suggested as a solution. In this work, the host–guest inclusion complex between the ß-CD and EST has been prepared using four different methods. The obtained samples have been deeply characterized using (13)C CP MAS solid state NMR, PXRD, FT-IR, TGA, DSC, and SEM. Using SCXRD, the crystal structure of the complex has been determined, being to the best of our knowledge the first solved crystal structure of an estrogen/CD complex. The periodic DFT calculations of NMR properties using GIPAW were found to be particularly helpful in the analysis of disorder in the solid state and interpretation of experimental NMR results. This work highlights the importance of a combined ssNMR/SCXRD approach to studying the structure of the inclusion complexes formed by cyclodextrins. MDPI 2023-04-26 /pmc/articles/PMC10180119/ /pubmed/37175157 http://dx.doi.org/10.3390/molecules28093747 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 Mazurek, Anna Helena Szeleszczuk, Łukasz Bethanis, Kostas Christoforides, Elias Dudek, Marta Katarzyna Zielińska-Pisklak, Monika Pisklak, Dariusz Maciej 17-β-Estradiol—β-Cyclodextrin Complex as Solid: Synthesis, Structural and Physicochemical Characterization |
title | 17-β-Estradiol—β-Cyclodextrin Complex as Solid: Synthesis, Structural and Physicochemical Characterization |
title_full | 17-β-Estradiol—β-Cyclodextrin Complex as Solid: Synthesis, Structural and Physicochemical Characterization |
title_fullStr | 17-β-Estradiol—β-Cyclodextrin Complex as Solid: Synthesis, Structural and Physicochemical Characterization |
title_full_unstemmed | 17-β-Estradiol—β-Cyclodextrin Complex as Solid: Synthesis, Structural and Physicochemical Characterization |
title_short | 17-β-Estradiol—β-Cyclodextrin Complex as Solid: Synthesis, Structural and Physicochemical Characterization |
title_sort | 17-β-estradiol—β-cyclodextrin complex as solid: synthesis, structural and physicochemical characterization |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10180119/ https://www.ncbi.nlm.nih.gov/pubmed/37175157 http://dx.doi.org/10.3390/molecules28093747 |
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