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Preparation and Characterization of a Hybrid Complex of Cyclodextrin-Based Metal—Organic Frameworks-1 and Ascorbic Acid Derivatives
Cyclodextrin-based metal–organic frameworks-1 (CD-MOF-1) prepared using potassium hydroxide, ethanol, and γ-cyclodextrin (γ-CD) has been reported as a new type of MOF for the development of pharmaceutical formulations. The present study aimed to investigate the physicochemical properties of ascorbic...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8658738/ https://www.ncbi.nlm.nih.gov/pubmed/34885460 http://dx.doi.org/10.3390/ma14237309 |
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author | Nanri, Ayumi Yoshida, Masaaki Ishida, Yoshiyuki Nakata, Daisuke Terao, Keiji Arce, Florencio Jr See, Gerard Lee Tanikawa, Takashi Inoue, Yutaka |
author_facet | Nanri, Ayumi Yoshida, Masaaki Ishida, Yoshiyuki Nakata, Daisuke Terao, Keiji Arce, Florencio Jr See, Gerard Lee Tanikawa, Takashi Inoue, Yutaka |
author_sort | Nanri, Ayumi |
collection | PubMed |
description | Cyclodextrin-based metal–organic frameworks-1 (CD-MOF-1) prepared using potassium hydroxide, ethanol, and γ-cyclodextrin (γ-CD) has been reported as a new type of MOF for the development of pharmaceutical formulations. The present study aimed to investigate the physicochemical properties of ascorbic acid derivatives (L-ascorbyl 6-palmitate (ASCP); L-ascorbyl 2,6-palmitate (ASCDP)) complexed with CD-MOF-1 by a solvent evaporation method. Powder X-ray diffraction revealed that the crystal diffraction pattern of CD-MOF-1 changed from α-type to β-type when prepared by a solvent evaporation method. For ASCP/CD-MOF-1 = 1/2 and ASCDP/CD-MOF-1 = 1/4 evaporated samples, the crystal diffraction peaks derived from ASCP and ASCDP disappeared, indicating a β-like behavior. Differential scanning calorimetry results revealed that the endothermic peaks of evaporated samples (ASCP/CD-MOF-1 = 1/2 and ASCDP/CD-MOF-1 = 1/4) were not detected due to melting. Furthermore, intermolecular interactions were observed in the hydrogen bonds between the CH groups of the side chains of ASCP and ASCDP and the OH group of CD-MOF-1 in (ASCP/CD-MOF-1 = 1/2) and EVP (ASCDP/CD-MOF-1 = 1/4), based on the near-infrared absorption spectroscopy analysis. CD-MOF-1 did not form inclusion complexes with the lactone rings of ASCP and ASCDP, but with the lipophilic side chains. These results suggested that CD-MOF-1 may be useful in preparing novel drug carriers for ASCP and ASCDP. |
format | Online Article Text |
id | pubmed-8658738 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-86587382021-12-10 Preparation and Characterization of a Hybrid Complex of Cyclodextrin-Based Metal—Organic Frameworks-1 and Ascorbic Acid Derivatives Nanri, Ayumi Yoshida, Masaaki Ishida, Yoshiyuki Nakata, Daisuke Terao, Keiji Arce, Florencio Jr See, Gerard Lee Tanikawa, Takashi Inoue, Yutaka Materials (Basel) Article Cyclodextrin-based metal–organic frameworks-1 (CD-MOF-1) prepared using potassium hydroxide, ethanol, and γ-cyclodextrin (γ-CD) has been reported as a new type of MOF for the development of pharmaceutical formulations. The present study aimed to investigate the physicochemical properties of ascorbic acid derivatives (L-ascorbyl 6-palmitate (ASCP); L-ascorbyl 2,6-palmitate (ASCDP)) complexed with CD-MOF-1 by a solvent evaporation method. Powder X-ray diffraction revealed that the crystal diffraction pattern of CD-MOF-1 changed from α-type to β-type when prepared by a solvent evaporation method. For ASCP/CD-MOF-1 = 1/2 and ASCDP/CD-MOF-1 = 1/4 evaporated samples, the crystal diffraction peaks derived from ASCP and ASCDP disappeared, indicating a β-like behavior. Differential scanning calorimetry results revealed that the endothermic peaks of evaporated samples (ASCP/CD-MOF-1 = 1/2 and ASCDP/CD-MOF-1 = 1/4) were not detected due to melting. Furthermore, intermolecular interactions were observed in the hydrogen bonds between the CH groups of the side chains of ASCP and ASCDP and the OH group of CD-MOF-1 in (ASCP/CD-MOF-1 = 1/2) and EVP (ASCDP/CD-MOF-1 = 1/4), based on the near-infrared absorption spectroscopy analysis. CD-MOF-1 did not form inclusion complexes with the lactone rings of ASCP and ASCDP, but with the lipophilic side chains. These results suggested that CD-MOF-1 may be useful in preparing novel drug carriers for ASCP and ASCDP. MDPI 2021-11-29 /pmc/articles/PMC8658738/ /pubmed/34885460 http://dx.doi.org/10.3390/ma14237309 Text en © 2021 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 Nanri, Ayumi Yoshida, Masaaki Ishida, Yoshiyuki Nakata, Daisuke Terao, Keiji Arce, Florencio Jr See, Gerard Lee Tanikawa, Takashi Inoue, Yutaka Preparation and Characterization of a Hybrid Complex of Cyclodextrin-Based Metal—Organic Frameworks-1 and Ascorbic Acid Derivatives |
title | Preparation and Characterization of a Hybrid Complex of Cyclodextrin-Based Metal—Organic Frameworks-1 and Ascorbic Acid Derivatives |
title_full | Preparation and Characterization of a Hybrid Complex of Cyclodextrin-Based Metal—Organic Frameworks-1 and Ascorbic Acid Derivatives |
title_fullStr | Preparation and Characterization of a Hybrid Complex of Cyclodextrin-Based Metal—Organic Frameworks-1 and Ascorbic Acid Derivatives |
title_full_unstemmed | Preparation and Characterization of a Hybrid Complex of Cyclodextrin-Based Metal—Organic Frameworks-1 and Ascorbic Acid Derivatives |
title_short | Preparation and Characterization of a Hybrid Complex of Cyclodextrin-Based Metal—Organic Frameworks-1 and Ascorbic Acid Derivatives |
title_sort | preparation and characterization of a hybrid complex of cyclodextrin-based metal—organic frameworks-1 and ascorbic acid derivatives |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8658738/ https://www.ncbi.nlm.nih.gov/pubmed/34885460 http://dx.doi.org/10.3390/ma14237309 |
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