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Open AccessArticle

Inclusion of Hydroxycinnamic Acids in Methylated Cyclodextrins: Host-Guest Interactions and Effects on Guest Thermal Stability

Centre for Supramolecular Chemistry Research, Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa
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Biomolecules 2021, 11(1), 45; https://doi.org/10.3390/biom11010045
Received: 29 November 2020 / Revised: 25 December 2020 / Accepted: 27 December 2020 / Published: 31 December 2020
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
There is ongoing interest in exploiting the antioxidant activity and other medicinal properties of natural monophenolic/polyphenolic compounds, but their generally low aqueous solubility limits their applications. Numerous studies have been undertaken to solubilize such compounds via supramolecular derivatization with co-crystal formation with biocompatible coformer molecules and cyclodextrin (CD) complexation being two successful approaches. In this study, eight new crystalline products obtained by complexation between methylated cyclodextrins and the bioactive phenolic acids (ferulic, hydroferulic, caffeic, and p-coumaric acids) were investigated using thermal analysis (hot stage microscopy, thermogravimetry, differential scanning calorimetry) and X-ray diffraction. All of the complexes crystallized as ternary systems containing the host CD, a phenolic acid guest, and water. On heating each complex, the primary thermal events were dehydration and liberation of the respective phenolic acid component, the mass loss for the latter step enabling determination of the host-guest stoichiometry. Systematic examination of the X-ray crystal structures of the eight complexes enabled their classification according to the extent of inclusion of each guest molecule within the cavity of its respective CD molecule. This revealed three CD inclusion compounds with full guest encapsulation, three with partial guest inclusion, and two that belong to the rare class of ‘non-inclusion’ compounds. View Full-Text
Keywords: cyclodextrins; hydroxycinnamic acids; complexation; thermal analysis; X-ray diffraction; inclusion compounds; self-inclusion; non-inclusion compounds cyclodextrins; hydroxycinnamic acids; complexation; thermal analysis; X-ray diffraction; inclusion compounds; self-inclusion; non-inclusion compounds
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MDPI and ACS Style

Hunt, L.E.; Bourne, S.A.; Caira, M.R. Inclusion of Hydroxycinnamic Acids in Methylated Cyclodextrins: Host-Guest Interactions and Effects on Guest Thermal Stability. Biomolecules 2021, 11, 45. https://doi.org/10.3390/biom11010045

AMA Style

Hunt LE, Bourne SA, Caira MR. Inclusion of Hydroxycinnamic Acids in Methylated Cyclodextrins: Host-Guest Interactions and Effects on Guest Thermal Stability. Biomolecules. 2021; 11(1):45. https://doi.org/10.3390/biom11010045

Chicago/Turabian Style

Hunt, Lee E.; Bourne, Susan A.; Caira, Mino R. 2021. "Inclusion of Hydroxycinnamic Acids in Methylated Cyclodextrins: Host-Guest Interactions and Effects on Guest Thermal Stability" Biomolecules 11, no. 1: 45. https://doi.org/10.3390/biom11010045

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