Preparation and characterization of the inclusion complexes of equol with sulfobutylether-β-cyclodextrin: their antioxidant activity and dissolution evaluation

Preparation and characterization of the inclusion complexes of equol with... The formation of inclusion complexes between S-(−)-equol (SEq) and cyclodextrins (CDs) was investigated. The binding constant (K ) of the SEq/sulfobutylether-β-cyclodextrin (SBE-β-CD) inclusion complex was determined to be 1600 L/mol based on UV data. The phenyl ring of the SEq molecule was found to be inserted from the secondary hydroxyl face of the 1 1 SBE-β-CD as evidenced from H– H rotating frame nuclear Overhauser effect spectroscopy (ROESY) NMR. The ther - mal properties of the solid SEq/SBE-β-CD inclusion complexes prepared by physical mixing, kneading and freeze-drying methods were studied by differential scanning calorimetry. For the solid complex obtained by the freeze-drying method, the endothermic peak corresponding to the melting point of SEq disappeared. The solid SEq/SBE-β-CD complexes exhibited a high score in antioxidant activity evaluation tests compared to SEq alone. Dissolution test revealed that the solid complex obtained by freeze-drying method had improved dissolution of SEq. Keywords S-(−)-Equol · Sulfobutylether-β-cyclodextrin · Inclusion complexes · Antioxidant activity · Dissolution improvement Introduction inclusion complexes with hydrophobic molecules [5–7]. It is therefore used to stabilize pharmaceutics [8–11] and 7-Hydroxy-3-(4′-hydroxyphenyl)-chroman (Equol) is an improve their bioavailability [12, 13]. Various CD-contain- isoflavone and is known to be a nonsteroidal estrogen [1 ]. ing drugs are currently on the http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Inclusion Phenomena and Macrocyclic Chemistry Springer Journals

Preparation and characterization of the inclusion complexes of equol with sulfobutylether-β-cyclodextrin: their antioxidant activity and dissolution evaluation

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Publisher
Springer Journals
Copyright
Copyright © 2018 by Springer Science+Business Media B.V., part of Springer Nature
Subject
Chemistry; Organic Chemistry; Food Science; Crystallography and Scattering Methods
ISSN
1388-3127
eISSN
1573-1111
D.O.I.
10.1007/s10847-018-0813-1
Publisher site
See Article on Publisher Site

Abstract

The formation of inclusion complexes between S-(−)-equol (SEq) and cyclodextrins (CDs) was investigated. The binding constant (K ) of the SEq/sulfobutylether-β-cyclodextrin (SBE-β-CD) inclusion complex was determined to be 1600 L/mol based on UV data. The phenyl ring of the SEq molecule was found to be inserted from the secondary hydroxyl face of the 1 1 SBE-β-CD as evidenced from H– H rotating frame nuclear Overhauser effect spectroscopy (ROESY) NMR. The ther - mal properties of the solid SEq/SBE-β-CD inclusion complexes prepared by physical mixing, kneading and freeze-drying methods were studied by differential scanning calorimetry. For the solid complex obtained by the freeze-drying method, the endothermic peak corresponding to the melting point of SEq disappeared. The solid SEq/SBE-β-CD complexes exhibited a high score in antioxidant activity evaluation tests compared to SEq alone. Dissolution test revealed that the solid complex obtained by freeze-drying method had improved dissolution of SEq. Keywords S-(−)-Equol · Sulfobutylether-β-cyclodextrin · Inclusion complexes · Antioxidant activity · Dissolution improvement Introduction inclusion complexes with hydrophobic molecules [5–7]. It is therefore used to stabilize pharmaceutics [8–11] and 7-Hydroxy-3-(4′-hydroxyphenyl)-chroman (Equol) is an improve their bioavailability [12, 13]. Various CD-contain- isoflavone and is known to be a nonsteroidal estrogen [1 ]. ing drugs are currently on the

Journal

Journal of Inclusion Phenomena and Macrocyclic ChemistrySpringer Journals

Published: Jun 6, 2018

References

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