Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Nanri, Ayumi, Yoshida, Masaaki, Ishida, Yoshiyuki, Nakata, Daisuke, Terao, Keiji, Arce, Florencio Jr, See, Gerard Lee, Tanikawa, Takashi, Inoue, Yutaka
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
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
_version_ 1784612801172471808
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
work_keys_str_mv AT nanriayumi preparationandcharacterizationofahybridcomplexofcyclodextrinbasedmetalorganicframeworks1andascorbicacidderivatives
AT yoshidamasaaki preparationandcharacterizationofahybridcomplexofcyclodextrinbasedmetalorganicframeworks1andascorbicacidderivatives
AT ishidayoshiyuki preparationandcharacterizationofahybridcomplexofcyclodextrinbasedmetalorganicframeworks1andascorbicacidderivatives
AT nakatadaisuke preparationandcharacterizationofahybridcomplexofcyclodextrinbasedmetalorganicframeworks1andascorbicacidderivatives
AT teraokeiji preparationandcharacterizationofahybridcomplexofcyclodextrinbasedmetalorganicframeworks1andascorbicacidderivatives
AT arceflorenciojr preparationandcharacterizationofahybridcomplexofcyclodextrinbasedmetalorganicframeworks1andascorbicacidderivatives
AT seegerardlee preparationandcharacterizationofahybridcomplexofcyclodextrinbasedmetalorganicframeworks1andascorbicacidderivatives
AT tanikawatakashi preparationandcharacterizationofahybridcomplexofcyclodextrinbasedmetalorganicframeworks1andascorbicacidderivatives
AT inoueyutaka preparationandcharacterizationofahybridcomplexofcyclodextrinbasedmetalorganicframeworks1andascorbicacidderivatives