Molecular modeling of β-cyclodextrin inclusion complexes with pharmaceutical compounds

Alcaro, Stefano; Battaglia, Danilo; Ortuso, Francesco

doi:10.3998/ark.5550190.0005.511

Cited by 7 publications

(1 citation statement)

References 10 publications

(13 reference statements)

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“…The difficulty in obtaining high-quality single crystals suitable for X-ray diffraction (XRD) has meant that only a few solid-state structures have been fully determined for CD inclusion compounds containing metallo-organic complexes. Nevertheless, full characterization using other methods such as powder XRD and NMR can provide important structural information. 12e, Molecular modeling calculations also help to investigate host−guest interactions and predict possible binding modes. 8k-m,9c, Herein, we describe a combined theoretical (ab initio calculations)−experimental (powder XRD, TGA, solid-state NMR, and vibrational spectroscopy) study of the encapsulation of Cp 2 NbCl 2 in β-CD and permethylated β-CD (TRIMEB).…”

Section: Introductionmentioning

confidence: 99%

A Combined Theoretical−Experimental Study of the Inclusion of Niobocene Dichloride in Native and Permethylated β-Cyclodextrins

et al. 2007

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Inclusion complexes comprising niobocene dichloride, Cp 2 NbCl 2 , and either native -cyclodextrin ( -CD) or permethylated -CD (TRIMEB) were prepared with a host:guest molar ratio of 1:1. The adducts were characterized in the solid state by powder X-ray diffraction (XRD), thermogravimetric analysis (TGA), 13 C{ 1 H} CP/MAS NMR, FTIR, and FT Raman spectroscopies. Ab initio calculations were performed in order to elucidate the possible inclusion geometries and calculate vibrational frequencies for Cp 2 NbCl 2 in the region 100-1800 cm -1 . The vibrational spectra indicated that neither the hosts nor the guest were chemically modified upon inclusion complexation. Small wavenumber shifts in C-H, C-C, and metal-ligand vibrational modes were attributed to the effect of the host-guest interaction. Powder XRD showed that the -CD adduct was of low crystallinity, while the TRIMEB adduct was quite crystalline. The powder XRD pattern of the TRIMEB adduct could be satisfactorily indexed in the monoclinic system with the space group P2 1 . A hypothetical structural model for the crystal packing was obtained through Monte Carlo optimizations using a reported TRIMEB geometry comprising a distorted elliptical cavity. An unrestrained Rietveld refinement of the structural model could not be carried out due to the relatively low quality of the experimental powder XRD pattern. However, the plausibility of the host-guest interaction geometry, involving inclusion of one of the guest Cp ligands inside the CD cavity, was fully supported by the ab initio calculations.

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Section: Introductionmentioning

confidence: 99%

A Combined Theoretical−Experimental Study of the Inclusion of Niobocene Dichloride in Native and Permethylated β-Cyclodextrins

et al. 2007

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Bindungsmechanismen in supramolekularen Komplexen

Schneider

2009

Angewandte Chemie

185

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Kräfte‐Sammelsurium: Supramolekulare Komplexe, wie der gezeigte, beruhen meist auf einer Kombination unterschiedlichster Wechselwirkungen, wie Ionenpaarbildung, Wasserstoffbrücken und Stapelwechselwirkungen. Die nicht immer einfache Charakterisierung von Natur und Stärke der intermolekularen Kräfte liefert Beiträge zum Verständnis biomimetischer Systeme wie auch zum Design von synthetischen Rezeptoren, Wirkstoffen und intelligenten Materialien. Die supramolekulare Chemie hat in den letzten Jahren eine enorme Ausdehnung erfahren, sowohl mit Blick auf mögliche Anwendungen wie auch auf analoge biologische Systeme. Bildung und Funktion supramolekularer Komplexe werden durch eine Vielzahl von oft schwer zu differenzierenden nichtkovalenten Kräften bestimmt. Ziel dieses Aufsatzes ist es, die entscheidenden Wechselwirkungsmechanismen zusammenhängend darzustellen und das Gesamtgebiet auf diese Weise zu klassifizieren. Als Beispiele werden meist organische Wirt‐Gast‐Komplexe gewählt, unter Berücksichtigung auch von biologisch relevanten Fragestellungen. Das Verständnis und die Quantifizierung der intermolekularen Wechselwirkungen ist für die rationale Planung neuer supramolekularer Systeme, einschließlich intelligenter Materialien, ebenso von Bedeutung wie für die Entwicklung neuer Wirkstoffe.

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Binding Mechanisms in Supramolecular Complexes

2009

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Supramolecular chemistry has expanded dramatically in recent years both in terms of potential applications and in its relevance to analogous biological systems. The formation and function of supramolecular complexes occur through a multiplicity of often difficult to differentiate noncovalent forces. The aim of this Review is to describe the crucial interaction mechanisms in context, and thus classify the entire subject. In most cases, organic host-guest complexes have been selected as examples, but biologically relevant problems are also considered. An understanding and quantification of intermolecular interactions is of importance both for the rational planning of new supramolecular systems, including intelligent materials, as well as for developing new biologically active agents.

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Molecular modeling of β-cyclodextrin inclusion complexes with pharmaceutical compounds

Cited by 7 publications

References 10 publications

A Combined Theoretical−Experimental Study of the Inclusion of Niobocene Dichloride in Native and Permethylated β-Cyclodextrins

A Combined Theoretical−Experimental Study of the Inclusion of Niobocene Dichloride in Native and Permethylated β-Cyclodextrins

Bindungsmechanismen in supramolekularen Komplexen

Binding Mechanisms in Supramolecular Complexes

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