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https://hdl.handle.net/2440/81535
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dc.contributor.author | Wallace, S. | - |
dc.contributor.author | Kee, T. | - |
dc.contributor.author | Huang, D. | - |
dc.date.issued | 2013 | - |
dc.identifier.citation | The Journal of Physical Chemistry B: Biophysical Chemistry, Biomaterials, Liquids, and Soft Matter, 2013; 117(41):12375-12382 | - |
dc.identifier.issn | 1520-6106 | - |
dc.identifier.issn | 1520-5207 | - |
dc.identifier.uri | http://hdl.handle.net/2440/81535 | - |
dc.description.abstract | Curcumin 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.statementofresponsibility | Samuel J. Wallace, Tak W. Kee, and David M. Huang | - |
dc.language.iso | en | - |
dc.publisher | Amer Chemical Soc | - |
dc.rights | Copyright © 2013 American Chemical Society | - |
dc.source.uri | http://dx.doi.org/10.1021/jp406125x | - |
dc.subject | Diamide | - |
dc.subject | Curcumin | - |
dc.subject | gamma-Cyclodextrins | - |
dc.subject | Binding Sites | - |
dc.subject | Molecular Structure | - |
dc.subject | Dimerization | - |
dc.subject | Models, Molecular | - |
dc.title | Molecular basis of binding and stability of curcumin in diamide-linked y-cyclodextrin dimers | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1021/jp406125x | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Kee, T. [0000-0002-4907-4663] | - |
dc.identifier.orcid | Huang, D. [0000-0003-2048-4500] | - |
Appears in Collections: | Aurora harvest Chemistry and Physics publications |
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