Cyclodextrin Molecular Reactors

Barr, L. W.; Dumanski, Paul G.; Easton, Christopher J.; Harper, Jason B.; Lee, Kitty; Lincoln, Stephen F.; Meyer, Adam G.; Simpson, Jamie S.

doi:10.1007/s10847-004-8833-9

Cited by 22 publications

(13 citation statements)

References 34 publications

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“…The applicability of cyclodextrins is closely related to the ability of this class of carbohydrate to form inclusion complexes with a very wide range of guest species in aqueous solutions. , The importance and use of CDs in the supramolecular context have been widely addressed in the literature. Due to its unique architecture, these molecules can be employed in synthesis of a large number of molecular devices such as molecular reactors, molecular nanotubes, molecular wires, and molecular shuttles. − In addition, CDs have been also used in molecular recognition due to their stereoseletivity. − …”

Section: Introductionmentioning

confidence: 99%

Ab Initio Calculations on Low-Energy Conformers of α-Cyclodextrin

et al. 2007

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In this article we carried out a comprehensive investigation of true minima on the potential energy surface (PES) for the alpha-cyclodextrin molecule using ab initio Hartree-Fock (HF) and density functional theory (DFT) quantum chemical methods, employing basis sets ranging from 6-31 G(d,p) to 6-311++G(2d,2p) triple-zeta quality. Thermodynamic quantities and the solvent effect were evaluated at the DFT level of theory. We believe that the most relevant conformers present on the multidimensional PES were sampled in our work, using an adequate treatment of electron correlation effects to describe the intramolecular hydrogen bonds that are present in cyclodextrin species. We present new structures not reported so far and discuss, in detail, the relevance of the DFT gas-phase equilibrium structures for the experimental and theoretical studies involving cyclodextrins and corresponding inclusion complexes, in the condensed phase. In addition, among the various true minimum energy structures located on the DFT PES, the preferred structures in the gas phase and aqueous media, needed to be used as representative minima on the PES in further studies involving the interaction of alpha-cyclodextrin with other species, were unambiguously identified.

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Section: Introductionmentioning

confidence: 99%

Ab Initio Calculations on Low-Energy Conformers of α-Cyclodextrin

et al. 2007

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“…As CDs são capazes de complexar e de estabilizar um largo espectro de substâncias, essa característica, associada às outras propriedades das CDs já citadas, faz delas uma grande atração para um variado número de aplicações industriais. As vantagens em potencial do uso e da disponibilidade das CDs têm tido papel decisivo no crescente interesse pelas mesmas, podendo ser usadas em fármacos, alimentos, cosméticos, etc, para estabilizar frente à radiação UV [4], temperatura, oxidação e hidrólise; aumentar a solubilidade em água [5]; mudanças de propriedades reológicas; liberação controlada de ingredientes ativos; mascarar odores e gostos desagradáveis; aumentar a biodisponibilidade; modelo de enzi-ma [6]; extração seletiva, adsorção de poluentes [7] e reatores moleculares [8].…”

Section: Palavras-chaveunclassified

Degradação hidrolítica e fotoquímica da amoxicilina na presença de β-ciclodextrina

et al. 2008

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Este trabalho tem como propósito monitorar a degradação do fármaco amoxicilina na presença e ausência de β-ciclodextrina através de técnicas espectroscópicas. Para isto, foi acompanhada a hidrólise do fármaco protegido da luz por cerca de 400 horas. Os resultados obtidos indicam que, inicialmente, a ciclodextrina não altera a hidrólise da amoxicilina, entretanto, após 250 horas de monitoramento há um aumento acentuado na hidrólise da amoxicilina quando presente a ciclodextrina. Ao irradiar a amostra com radiação UV, verificamos que as soluções contendo β-ciclodextrina sofrem uma fototransformação mais lenta (26,8%) que as soluções sem β-ciclodextrina.

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“…5 Cyclodextrins have also proved to be capable of mediating many organic transformations, either by providing a confined reaction field or by participating in the transformation of bound substrates with their functional groups. 6 Introduction of additional binding sites and/or functional groups into cyclodextrins improves greatly their catalytic ability or even results in the finding of novel functions. 7 Among the many cyclodextrin derivatives, cyclodextrin dimers and oligomers have attracted special interest.…”

Section: Introductionmentioning

confidence: 99%

Cerium complexes of cyclodextrin dimers as efficient catalysts for luminol chemiluminescence reactions

Yuan

Atsumi

et al. 2007

Org. Biomol. Chem.

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The chemiluminescence of a luminol-H(2)O(2) system is found to be remarkably enhanced by the Ce(IV) complexes of EDTA-bridged cyclodextrin dimers. The dimers were proved to work much more efficiently than the corresponding monomer. The cavity shape of cyclodextrin moieties and their cooperation displayed an important role in amplifying the chemiluminescence. Further modification of either the cyclodextrin rims or the EDTA linker altered significantly the catalytic abilities of the cyclodextrin dimers, and the examination of the effect of substituents on the chemiluminescence outputs suggested that the proximity between the cyclodextrin cavity and the metallic center might account for the amelioration of the chemiluminescence output.

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Cyclodextrin Molecular Reactors

Cited by 22 publications

References 34 publications

Ab Initio Calculations on Low-Energy Conformers of α-Cyclodextrin

Ab Initio Calculations on Low-Energy Conformers of α-Cyclodextrin

Degradação hidrolítica e fotoquímica da amoxicilina na presença de β-ciclodextrina

Cerium complexes of cyclodextrin dimers as efficient catalysts for luminol chemiluminescence reactions

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