{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:58:42Z","timestamp":1787029122211,"version":"build-2736575974"},"reference-count":51,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2023,9,29]],"date-time":"2023-09-29T00:00:00Z","timestamp":1695945600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Conventionally, methanol is the solvent of choice in the synthesis of gamma-cyclodextrin metal-organic frameworks (\u03b3-CD-MOFs), but using ethanol as a replacement could allow for a more food-grade synthesis condition. Therefore, the aim of the study was to compare the \u03b3-CD-MOFs synthesised with both methanol and ethanol. The \u03b3-CD-MOFs were characterised by scanning electron microscopy (SEM), surface area and pore measurement, Fourier transform infrared spectroscopy (FTIR) and powder X-ray diffraction (PXRD). The encapsulation efficiency (EE) and loading capacity (LC) of the \u03b3-CD-MOFs were also determined for curcumin, using methanol, ethanol and a mixture of the two as encapsulation solvent. It was found that \u03b3-CD-MOFs synthesised by methanol and ethanol do not differ greatly, the most significant difference being the larger crystal size of \u03b3-CD-MOFs crystallised from ethanol. However, the change in solvent significantly influenced the EE and LC of the crystals. The higher solubility of curcumin in ethanol reduced interactions with the \u03b3-CD-MOFs and resulted in lowered EE and LC. This suggests that different solvents should be used to deliberately manipulate the EE and LC of target compounds for better use of \u03b3-CD-MOFs as their encapsulating and delivery agents.<\/jats:p>","DOI":"10.3390\/molecules28196876","type":"journal-article","created":{"date-parts":[[2023,10,2]],"date-time":"2023-10-02T04:39:30Z","timestamp":1696221570000},"page":"6876","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["\u03b3-Cyclodextrin Metal-Organic Frameworks: Do Solvents Make a Difference?"],"prefix":"10.3390","volume":"28","author":[{"given":"Jia X.","family":"Oh","sequence":"first","affiliation":[{"name":"Food Colloids and Bioprocessing Group, School of Food Science and Nutrition, University of Leeds, Leeds LS2 9JT, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6493-1547","authenticated-orcid":false,"given":"Brent S.","family":"Murray","sequence":"additional","affiliation":[{"name":"Food Colloids and Bioprocessing Group, School of Food Science and Nutrition, University of Leeds, Leeds LS2 9JT, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5681-0593","authenticated-orcid":false,"given":"Alan R.","family":"Mackie","sequence":"additional","affiliation":[{"name":"Food Colloids and Bioprocessing Group, School of Food Science and Nutrition, University of Leeds, Leeds LS2 9JT, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rammile","family":"Ettelaie","sequence":"additional","affiliation":[{"name":"Food Colloids and Bioprocessing Group, School of Food Science and Nutrition, University of Leeds, Leeds LS2 9JT, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Amin","family":"Sadeghpour","sequence":"additional","affiliation":[{"name":"Food Colloids and Bioprocessing Group, School of Food Science and Nutrition, University of Leeds, Leeds LS2 9JT, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ruggero","family":"Frison","sequence":"additional","affiliation":[{"name":"Physik-Institut, Universit\u00e4t Z\u00fcrich, Winterthurerstrasse 190, CH-8057 Z\u00fcrich, Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,9,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"805","DOI":"10.1021\/acs.accounts.6b00577","article-title":"Postsynthetic Tuning of Metal\u2013Organic Frameworks for Targeted Applications","volume":"50","author":"Islamoglu","year":"2017","journal-title":"Acc. Chem. Res."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Tibbetts, I., and Kostakis, G.E. (2020). Recent Bio-Advances in Metal-Organic Frameworks. Molecules, 25.","DOI":"10.3390\/molecules25061291"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"44507","DOI":"10.1021\/acsomega.2c05310","article-title":"Review on Metal\u2013Organic Framework Classification, Synthetic Approaches, and Influencing Factors: Applications in Energy, Drug Delivery, and Wastewater Treatment","volume":"7","author":"Yusuf","year":"2022","journal-title":"ACS Omega"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1289","DOI":"10.1021\/acs.jchemed.2c00922","article-title":"CD-MOF-1 for CO2 Uptake: Remote and Hybrid Green Chemistry Synthesis of a Framework Material with Environmentally Conscious Applications","volume":"100","author":"Benedetto","year":"2023","journal-title":"J. Chem. Educ."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"869","DOI":"10.1021\/cr200190s","article-title":"Metal\u2013Organic Frameworks for Separations","volume":"112","author":"Li","year":"2012","journal-title":"Chem. Rev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1016\/j.ccr.2019.03.005","article-title":"Functional Metal\u2013Organic Frameworks for Catalytic Applications","volume":"388","author":"Xu","year":"2019","journal-title":"Coord. Chem. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1343","DOI":"10.2217\/nnm-2018-0347","article-title":"Recent Progress in Nanoscale Metal-Organic Frameworks for Drug Release and Cancer Therapy","volume":"14","author":"He","year":"2019","journal-title":"Nanomedicine"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1440","DOI":"10.1021\/acs.accounts.0c00695","article-title":"Cyclodextrin Metal\u2013Organic Frameworks and Their Applications","volume":"54","author":"Roy","year":"2021","journal-title":"Acc. Chem. Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1016\/j.cofs.2021.02.008","article-title":"Cyclodextrin-Metal-Organic Frameworks (CD-MOFs): Main Aspects and Perspectives in Food Applications","volume":"41","author":"Shen","year":"2021","journal-title":"Curr. Opin. Food Sci."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"8630","DOI":"10.1002\/anie.201002343","article-title":"Metal\u2013Organic Frameworks from Edible Natural Products","volume":"49","author":"Smaldone","year":"2010","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"485","DOI":"10.1016\/j.foodchem.2016.06.013","article-title":"Encapsulation of Curcumin in Cyclodextrin-Metal Organic Frameworks: Dissociation of Loaded CD-MOFs Enhances Stability of Curcumin","volume":"212","author":"Moussa","year":"2016","journal-title":"Food Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"128978","DOI":"10.1016\/j.foodchem.2020.128978","article-title":"Novel \u03b3-Cyclodextrin-Metal\u2013Organic Frameworks for Encapsulation of Curcumin with Improved Loading Capacity, Physicochemical Stability and Controlled Release Properties","volume":"347","author":"Chen","year":"2021","journal-title":"Food Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"10795","DOI":"10.1039\/D1FO02087K","article-title":"Encapsulation of Curcumin in CD-MOFs: Promoting Its Incorporation into Water-Based Products and Consumption","volume":"12","author":"Sun","year":"2021","journal-title":"Food Funct."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1016\/j.jcis.2019.06.064","article-title":"Development of Nanoscale Bioactive Delivery Systems Using Sonication: Glycyrrhizic Acid-Loaded Cyclodextrin Metal-Organic Frameworks","volume":"553","author":"Qiu","year":"2019","journal-title":"J. Colloid Interface Sci."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"126328","DOI":"10.1016\/j.foodchem.2020.126328","article-title":"Resveratrol-Loaded Core-Shell Nanostructured Delivery Systems: Cyclodextrin-Based Metal-Organic Nanocapsules Prepared by Ionic Gelation","volume":"317","author":"Qiu","year":"2020","journal-title":"Food Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/j.ijpharm.2018.11.074","article-title":"A \u201cShip-in-a-Bottle\u201d Strategy to Create Folic Acid Nanoclusters inside the Nanocages of \u03b3-Cyclodextrin Metal-Organic Frameworks","volume":"556","author":"Xu","year":"2019","journal-title":"Int. J. Pharm."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"133553","DOI":"10.1016\/j.foodchem.2022.133553","article-title":"Encapsulation of Catechin into Nano-Cyclodextrin-Metal-Organic Frameworks: Preparation, Characterization, and Evaluation of Storage Stability and Bioavailability","volume":"394","author":"Jiang","year":"2022","journal-title":"Food Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1016\/j.fshw.2012.08.003","article-title":"Hypothesis Review: The Direct Interaction of Food Nanoparticles with the Lymphatic System","volume":"1","author":"Lu","year":"2012","journal-title":"Food Sci. Hum. Wellness"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"127348","DOI":"10.1016\/j.jcrysgro.2023.127348","article-title":"Size Optimization of Mesoporous \u03b2-Cyclodextrin Metal-Organic Frameworks as Bio-MOFs","volume":"620","author":"Sadeh","year":"2023","journal-title":"J. Cryst. Growth"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"115935","DOI":"10.1016\/j.carbpol.2020.115935","article-title":"Activation of a Gamma\u2013Cyclodextrin\u2013Based Metal\u2013Organic Framework Using Supercritical Carbon Dioxide for High\u2013Efficient Delivery of Honokiol","volume":"235","author":"He","year":"2020","journal-title":"Carbohydr. Polym."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"212","DOI":"10.1016\/j.ijpharm.2016.09.029","article-title":"Optimized Synthesis and Crystalline Stability of \u03b3-Cyclodextrin Metal-Organic Frameworks for Drug Adsorption","volume":"514","author":"Liu","year":"2016","journal-title":"Int. J. Pharm."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"10566","DOI":"10.1002\/anie.201204919","article-title":"Nano- and Microsized Cubic Gel Particles from Cyclodextrin Metal\u2013Organic Frameworks","volume":"51","author":"Furukawa","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Tabanelli, R., Brogi, S., and Calderone, V. (2021). Improving Curcumin Bioavailability: Current Strategies and Future Perspectives. Pharmaceutics, 13.","DOI":"10.3390\/pharmaceutics13101715"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Stohs, S.J., Chen, O., Ray, S.D., Ji, J., Bucci, L.R., and Preuss, H.G. (2020). Highly Bioavailable Forms of Curcumin and Promising Avenues for Curcumin-Based Research and Application: A Review. Molecules, 25.","DOI":"10.3390\/molecules25061397"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1016\/j.tifs.2021.02.006","article-title":"Recent Advances to Improve Curcumin Oral Bioavailability","volume":"110","author":"Sabet","year":"2021","journal-title":"Trends Food Sci. Technol."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/j.tifs.2017.11.009","article-title":"Recent Advances in Emulsion-Based Delivery Approaches for Curcumin: From Encapsulation to Bioaccessibility","volume":"71","author":"Akhtar","year":"2018","journal-title":"Trends Food Sci. Technol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"5153","DOI":"10.1007\/s13197-019-03986-1","article-title":"A Critical Review of Analytical Methods for Determination of Curcuminoids in Turmeric","volume":"56","author":"Kotra","year":"2019","journal-title":"J. Food Sci. Technol."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"6387","DOI":"10.1002\/jsfa.12004","article-title":"Effect of Potassium Salts on the Structure of \u03b3-Cyclodextrin MOF and the Encapsulation Properties with Thymol","volume":"102","author":"Pan","year":"2022","journal-title":"J. Sci. Food Agric."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1143","DOI":"10.1021\/acs.cgd.1c01091","article-title":"Crystalline Rearranged CD-MOF Particles Obtained via Spray-Drying Synthesis Applied to Inhalable Formulations with High Drug Loading","volume":"22","author":"Tse","year":"2022","journal-title":"Cryst. Growth Des."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1007\/s10847-019-00920-y","article-title":"Inclusion of Ethanol in a Nano-Porous, Bio-Based Metal Organic Framework","volume":"95","author":"Kathuria","year":"2019","journal-title":"J. Incl. Phenom. Macrocycl. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1397","DOI":"10.1111\/1541-4337.12515","article-title":"Antibacterial Applications of Metal\u2013Organic Frameworks and Their Composites","volume":"19","author":"Shen","year":"2020","journal-title":"Compr. Rev. Food Sci. Food Saf."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"9246","DOI":"10.1039\/C7CC03471G","article-title":"Moisture Resistant and Biofriendly CD-MOF Nanoparticles Obtained via Cholesterol Shielding","volume":"53","author":"Singh","year":"2017","journal-title":"Chem. Commun."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1030","DOI":"10.1107\/S0021889809040126","article-title":"Scherrer Grain-Size Analysis Adapted to Grazing-Incidence Scattering with Area Detectors. Erratum","volume":"42","author":"Smilgies","year":"2009","journal-title":"J. Appl. Crystallogr."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1016\/j.jiec.2018.12.048","article-title":"Cyclodextrin-Metal\u2013Organic Framework (CD-MOF): From Synthesis to Applications","volume":"72","author":"Rajkumar","year":"2019","journal-title":"J. Ind. Eng. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1007\/s11095-016-2059-1","article-title":"Improvement in Thermal Stability of Sucralose by \u03b3-Cyclodextrin Metal-Organic Frameworks","volume":"34","author":"Lv","year":"2017","journal-title":"Pharm. Res."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2200645","DOI":"10.1002\/mame.202200645","article-title":"In Situ Growth of Cyclodextrin-Based Metal Organic Framework Air Filters for Reusable SO2 Adsorbent Applications","volume":"308","author":"Kim","year":"2023","journal-title":"Macromol. Mater. Eng."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"84","DOI":"10.1016\/j.jcrysgro.2016.09.058","article-title":"Influence of Solvent Polarity and Supersaturation on Template-Induced Nucleation of Carbamazepine Crystal Polymorphs","volume":"469","author":"Parambil","year":"2017","journal-title":"J. Cryst. Growth"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4403","DOI":"10.1021\/acs.cgd.8b00371","article-title":"Crystal Shape Modification via Cycles of Growth and Dissolution in a Tubular Crystallizer","volume":"18","author":"Neugebauer","year":"2018","journal-title":"Cryst. Growth Des."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2914","DOI":"10.1016\/j.apsb.2021.04.018","article-title":"Simultaneous Improvement to Solubility and Bioavailability of Active Natural Compound Isosteviol Using Cyclodextrin Metal-Organic Frameworks","volume":"11","author":"Chen","year":"2021","journal-title":"Acta Pharm. Sin. B"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"458","DOI":"10.1021\/ja808853q","article-title":"Supercritical Processing as a Route to High Internal Surface Areas and Permanent Microporosity in Metal\u2212Organic Framework Materials","volume":"131","author":"Nelson","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"7551","DOI":"10.1039\/C4TB00725E","article-title":"Supercritical Carbon Dioxide-Assisted Drug Loading and Release from Biocompatible Porous Metal\u2013Organic Frameworks","volume":"2","author":"Matsuyama","year":"2014","journal-title":"J. Mater. Chem. B"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"3048","DOI":"10.1208\/s12249-018-1136-7","article-title":"Characterization of Inclusion Complex of Coenzyme Q10 with the New Carrier CD-MOF-1 Prepared by Solvent Evaporation","volume":"19","author":"Inoue","year":"2018","journal-title":"AAPS PharmSciTech"},{"key":"ref_43","first-page":"2903","article-title":"Structural Investigation on Curcumin","volume":"20","author":"Gunasekaran","year":"2008","journal-title":"Asian J. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1007\/s11095-019-2650-3","article-title":"MOF Capacitates Cyclodextrin to Mega-Load Mode for High-Efficient Delivery of Valsartan","volume":"36","author":"Zhang","year":"2019","journal-title":"Pharm. Res."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"3887","DOI":"10.1002\/jsfa.11738","article-title":"Encapsulating Quercetin in Cyclodextrin Metal\u2013Organic Frameworks Improved Its Solubility and Bioavailability","volume":"102","author":"Wang","year":"2022","journal-title":"J. Sci. Food Agric."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"10322","DOI":"10.1039\/D3NJ00892D","article-title":"Novel \u03b3-Cyclodextrin-Based Metal\u2013Organic Frameworks for the Effective Encapsulation of Oregano Essential Oil and Controlled Release","volume":"47","author":"He","year":"2023","journal-title":"New J. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"105284","DOI":"10.1016\/j.foodhyd.2019.105284","article-title":"Curcumin-Loaded Pea Protein Isolate-High Methoxyl Pectin Complexes Induced by Calcium Ions: Characterization, Stability and in Vitro Digestibility","volume":"98","author":"Guo","year":"2020","journal-title":"Food Hydrocoll."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"116","DOI":"10.1016\/j.poly.2018.11.043","article-title":"Green Synthesis of \u03b2-Cyclodextrin Metal\u2013Organic Frameworks and the Adsorption of Quercetin and Emodin","volume":"159","author":"Yang","year":"2019","journal-title":"Polyhedron"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"132605","DOI":"10.1016\/j.foodchem.2022.132605","article-title":"Cyclodextrin-Based Metal\u2013Organic Framework Nanoparticles as Superior Carriers for Curcumin: Study of Encapsulation Mechanism, Solubility, Release Kinetics, and Antioxidative Stability","volume":"383","author":"Chen","year":"2022","journal-title":"Food Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"116795","DOI":"10.1016\/j.molliq.2021.116795","article-title":"Solubility Measurement and Thermodynamic Modelling of Curcumin in Twelve Pure Solvents and Three Binary Solvents at Different Temperature (T = 278.15\u2013323.15 K)","volume":"338","author":"Cui","year":"2021","journal-title":"J. Mol. Liq."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0921-4526(93)90108-I","article-title":"Recent Advances in Magnetic Structure Determination by Neutron Powder Diffraction","volume":"192","year":"1993","journal-title":"Phys. B Condens. 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