Pub Date : 2024-02-16DOI: 10.1007/s10847-024-01220-w
Ajay Kathuria, Lokesh Kumar, Kirtiraj K. Gaikwad, Amro El Badawy, Mohsen B. Kivy
Stabilization of reactive organic species by encapsulation in self-assembly supramolecules is a popular technique. Citral, a common antimicrobial and flavor compound, is highly sensitive to oxidation, especially when exposed to elevated temperature and light. In this study we evaluated the encapsulation efficiency of citral in cyclodextrin-metal organic framework (CDMOF) to prevent oxidation, provide chemical stability, and control the release of citral for various industrial applications including packaging. Computational simulations indicated the formation of stable inclusion complex between CDMOF and citral with binding energy of the IC approximately − 3.89 kcal mol−1. We observed around 11.83% w/w inclusion of citral in CDMOF as measured using TGA. Host–guest interactions between CDMOF and citral were further elucidated using FTIR, DSC, and SEM. Encapsulation of CDMOF in citral offers higher temperature stability, and extended-release kinetics.
{"title":"Micro-encapsulation of citral using edible γ-cyclodextrin metal organic framework","authors":"Ajay Kathuria, Lokesh Kumar, Kirtiraj K. Gaikwad, Amro El Badawy, Mohsen B. Kivy","doi":"10.1007/s10847-024-01220-w","DOIUrl":"https://doi.org/10.1007/s10847-024-01220-w","url":null,"abstract":"<p>Stabilization of reactive organic species by encapsulation in self-assembly supramolecules is a popular technique. Citral, a common antimicrobial and flavor compound, is highly sensitive to oxidation, especially when exposed to elevated temperature and light. In this study we evaluated the encapsulation efficiency of citral in cyclodextrin-metal organic framework (CDMOF) to prevent oxidation, provide chemical stability, and control the release of citral for various industrial applications including packaging. Computational simulations indicated the formation of stable inclusion complex between CDMOF and citral with binding energy of the IC approximately − 3.89 kcal mol<sup>−1</sup>. We observed around 11.83% w/w inclusion of citral in CDMOF as measured using TGA. Host–guest interactions between CDMOF and citral were further elucidated using FTIR, DSC, and SEM. Encapsulation of CDMOF in citral offers higher temperature stability, and extended-release kinetics.</p>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-02-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139761214","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-02-10DOI: 10.1007/s10847-024-01222-8
Abstract
Inclusion complexes of benzene (Bz) with cyclodextrins (CD) have been investigated so far using non-NMR techniques in various solvents resulting in conflicting data. Here, the first application of NMR spectroscopy in combination with rigorous statistical analysis of the results has allowed us to determine accurately the stoichiometry of complexes and their association constants. Titration measurements have been performed by 1H NMR spectroscopy in D2O at a magnetic field B0 of 14.1 T. αCD and γCD host molecules form weak 1 : 1 complexes with Bz. In contrast, Bz and βCD build 1 : 1 and 2 : 1 complexes coexisting in solution with large binding constants. Binding of second benzene molecule is strongly cooperative.
{"title":"NMR studies of complex formation between natural cyclodextrins and benzene","authors":"","doi":"10.1007/s10847-024-01222-8","DOIUrl":"https://doi.org/10.1007/s10847-024-01222-8","url":null,"abstract":"<h3>Abstract</h3> <p>Inclusion complexes of benzene (Bz) with cyclodextrins (CD) have been investigated so far using non-NMR techniques in various solvents resulting in conflicting data. Here, the first application of NMR spectroscopy in combination with rigorous statistical analysis of the results has allowed us to determine accurately the stoichiometry of complexes and their association constants. Titration measurements have been performed by <sup>1</sup>H NMR spectroscopy in D<sub>2</sub>O at a magnetic field B<sub>0</sub> of 14.1 T. αCD and γCD host molecules form weak 1 : 1 complexes with Bz. In contrast, Bz and βCD build 1 : 1 and 2 : 1 complexes coexisting in solution with large binding constants. Binding of second benzene molecule is strongly cooperative.</p>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139761212","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-11DOI: 10.1007/s10847-024-01218-4
Athar Karafi, Lassaad Baklouti, Besma Mellah
New coumarin derivatives C1, C2, and C3 with different substituents (methylphenyl, chlorophenyl, and nitrophenyl) were prepared and characterized using various spectroscopic techniques. C1 and C2 display luminescence when excited at 325 nm, while C3 has weak emission at 335 nm. The binding properties of these derivatives toward transition metals and lanthanum cations were studied using UV-visible absorption spectroscopy, and the former cations were found to form ML2 complexes by titration method. The chelation of each ligand with metal cations induced changes in their luminescence properties.
{"title":"Spectroscopic properties and stabilities of metal complexes using coumarin derivatives substituted with methyl, chloro, and nitro groups","authors":"Athar Karafi, Lassaad Baklouti, Besma Mellah","doi":"10.1007/s10847-024-01218-4","DOIUrl":"https://doi.org/10.1007/s10847-024-01218-4","url":null,"abstract":"<p>New coumarin derivatives <b>C1</b>, <b>C2</b>, and <b>C3</b> with different substituents (methylphenyl, chlorophenyl, and nitrophenyl) were prepared and characterized using various spectroscopic techniques. <b>C1</b> and <b>C2</b> display luminescence when excited at 325 nm, while <b>C3</b> has weak emission at 335 nm. The binding properties of these derivatives toward transition metals and lanthanum cations were studied using UV-visible absorption spectroscopy, and the former cations were found to form ML<sub>2</sub> complexes by titration method. The chelation of each ligand with metal cations induced changes in their luminescence properties.</p>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139463580","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-06DOI: 10.1007/s10847-023-01212-2
Xiang Li, Lijiao Chen, Yongning Yang, Mingfang Ma, Deng Liu, Zhaolou Li
A hydroxypropyl β-cyclodextrin (HPCD)/5-fluorouracil (5-FU) inclusion complex was loaded into konjac glucomannan hydrogel successfully by co-assembly. The influence of HPCD on the structure and properties of konjac glucomannan (KGM) hydrogel was investigated. The networks of KGM/HPCD hydrogel became flat and firm after HPCD intervened. The KGM/HPCD hydrogel had diversified microstructures including HPCD molecular cavities, porous lamellar structure in fibrous bands. The X-ray diffractometry (XRD) results reflected amorphous characters of the KGM/HPCD xerogel. The analytical data of Fourier transform infrared spectrometry (FT-IR) and differential scanning calorimetry (DSC) confirmed the supramolecular interactions between KGM and HPCD molecules in the gel network were mainly H-bonding interactions. HPCD improved KGM/HPCD hydrogel by crosslinking physically to construct a novel drug delivery system in the presence of sodium carbonate. The KGM/HPCD hydrogel achieved more effective and sustained drug release, in which HPCD cavities shared responsibility for the controlled release of chemotherapeutic 5-FU molecules. Rheological measurements also showed the presence of HPCD increased the elastic modulus (G') of the novel KGM/HPCD hydrogel.
Graphical abstract
Through co-assembly, a green drug delivery system was successfully constructed with hydroxypropyl β-cyclodextrin/5-fluorouracil inclusion complex loaded into konjac glucomannan hydrogel. By dialysis experiments, the drug 5-fluorouracil release rate from the inclusion complex loaded hydrogel was prolongated remarkably compared to that from single 5-fluorouracil loaded hydrogel. For the inclusion complex loaded hydrogel with different 5-fluorouracil concentrations, or under different physiological conditions, the drug cumulative release appeared also evident difference. This green drug delivery system has important potential application in medical engineering material.