Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/81535
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dc.contributor.authorWallace, S.-
dc.contributor.authorKee, T.-
dc.contributor.authorHuang, D.-
dc.date.issued2013-
dc.identifier.citationThe Journal of Physical Chemistry B: Biophysical Chemistry, Biomaterials, Liquids, and Soft Matter, 2013; 117(41):12375-12382-
dc.identifier.issn1520-6106-
dc.identifier.issn1520-5207-
dc.identifier.urihttp://hdl.handle.net/2440/81535-
dc.description.abstractCurcumin is a naturally occurring molecule with medicinal properties that is unstable in water, whose efficacy as a drug can potentially be enhanced by encapsulation inside a host molecule. In this work, the thermodynamics and mechanism of binding of curcumin to succinamide- and urea-linked γ-cyclodextrin (γ-CD) dimers in water are investigated by molecular dynamics simulations. The simulated binding constants of curcumin to succinamide- and urea-linked γ-CD dimers at 310 K are 11.3 × 10⁶ M ⁻¹ and 1.6 × 10⁶ M ⁻¹, respectively, matching well with previous experimental results of 8.7 × 10⁶ M ⁻¹ and 2.0 × 10⁶ M ⁻¹. The simulations reveal structural information about the encapsulation of curcumin inside the diamide-linked γ-CD dimers, with distinct qualitative differences observed for the two dimers. In particular, (1) the predominant orientation of curcumin inside the urea-linked γ-CD dimer is perpendicular to that in the succinamide-linked γ-CD dimer; (2) the magnitude of the angle between the planes of the cyclodextrins is larger for the succinamide-linked γ-CD dimer; and (3) curcumin exhibits greater configurational freedom inside the urea-linked γ-CD dimer. A consequence of some of these structural differences is that the dimer interior is more accessible to water in the succinamide-linked γ-CD dimer. These observations explain the higher stability and lower binding constant observed experimentally for curcumin in the urea-linked cyclodextrin γ-CD dimer compared with the succinamide-linked γ-CD dimer. More generally, the results demonstrate how stability and binding strength can be decoupled and thus separately optimized in host–guest systems used for drug delivery.-
dc.description.statementofresponsibilitySamuel J. Wallace, Tak W. Kee, and David M. Huang-
dc.language.isoen-
dc.publisherAmer Chemical Soc-
dc.rightsCopyright © 2013 American Chemical Society-
dc.subjectDiamide-
dc.subjectCurcumin-
dc.subjectgamma-Cyclodextrins-
dc.subjectBinding Sites-
dc.subjectMolecular Structure-
dc.subjectDimerization-
dc.subjectModels, Molecular-
dc.titleMolecular basis of binding and stability of curcumin in diamide-linked y-cyclodextrin dimers-
dc.typeJournal article-
dc.identifier.doi10.1021/jp406125x-
pubs.publication-statusPublished-
dc.identifier.orcidKee, T. [0000-0002-4907-4663]-
dc.identifier.orcidHuang, D. [0000-0003-2048-4500]-
Appears in Collections:Aurora harvest
Chemistry and Physics publications

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