Effect of the chiral discrimination on the vibrational properties of (R)-, (S)- and (R,S)-ibuprofen/methyl-β-cyclodextrin inclusion complexes

Crupi, V.; Guella, Graziano; Majolino, D.; Mancini, Ines; Paciaroni, Alessandro; Rossi, Barbara; Venuti, Valentina; Verrocchio, P.; Viliani, G.

doi:10.1080/14786435.2010.512575

Cited by 13 publications

(20 citation statements)

References 21 publications

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“…A well‐assessed curve fitting procedure was employed, in order to allow the deconvolution of the band observed between 1680 and 1800 cm −1 into its individual spectral components. The observation of two minima in the second derivative profiles of the experimental spectra suggests the presence of at least two sub‐bands for the C=O stretching region.…”

Section: Resultsmentioning

confidence: 99%

Connection between the vibrational dynamics and the cross‐linking properties in cyclodextrins‐based polymers

Crupi

Fontana

Giarola

et al. 2013

J Raman Spectroscopy

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The vibrational dynamics of a new class of cross‐linked polymers obtained from both native and modified cyclodextrin, referred to as cyclodextrin nanosponges, is here investigated. The main purpose is to spot the structure of these materials at molecular level unlikely to be characterized by diffraction methods due to the low or null degree of crystallinity. The analysis of the spectral features of the vibrational bands observed between 1650 and 1800 cm−1 in both Raman and infrared spectra, and assigned to the carbonyl stretching modes of the polymeric network, is performed by using band deconvolution procedures. At the same time, a detailed inspection of the low‐wavenumber vibrational dynamics of these polymers is carried out, focusing on the modifications occurring on the so‐called boson peak. The simultaneous analysis of different wavenumber ranges in Raman and infrared spectra of cyclodextrin nanosponges allows us to develop a reliable strategy for exploring both the cross‐linking degree and the elastic properties of these innovative materials. The overall results give a complete characterization of the structural and dynamical properties of the system, in turn strictly connected to the entrapment/transport ability of these polymeric matrices. Copyright © 2013 John Wiley & Sons, Ltd.

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Section: Resultsmentioning

confidence: 99%

Connection between the vibrational dynamics and the cross‐linking properties in cyclodextrins‐based polymers

Crupi

Fontana

Giarola

et al. 2013

J Raman Spectroscopy

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“…[1][2][3] The characteristic truncated-cone shape of CDs, having an inner hydrophobic cavity and an external hydrophilic surface, give them the remarkable property of acting as molecular hosts in the formation of inclusion complexes with a wide variety of hydrophobic guest molecules having appropriate chemical affinity, shape, and size. 1,2,4,5 The formation of such supramolecular aggregates is a well-assessed phenomenon with important applications covering a broad range of fields, including chiral separations, 6 drug delivery and targeting, 7-11 food chemistry, 12 and sensors. 13 This fact, added to the relatively simple production process, the absence of toxicity, and the low costs of CDs, which make them ideal materials for industrial uses, has motivated, for several decades, a considerable interest in CD.…”

Section: Introductionmentioning

confidence: 99%

Vibrational Properties of Cyclodextrin–Water Solutions Investigated by Low-Frequency Raman Scattering: Temperature and Concentration Effects

et al. 2010

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Depolarized low-frequency Raman spectra from several cyclodextrin-water solutions have been investigated as a function of both temperature and macrocycle concentration. The differences between the vibrational spectra of solutions and pure water have been discussed, focusing the attention on the modifications of the vibrational bands assigned to the H-bond bending and stretching intermolecular modes of water. These features are in turn related to the structural changes occurring in the H-bonded water molecules allowing us to evince a destructuring effect on the tetrahedral hydrogen bonding arrangements induced in solution by increasing temperature and solute concentration.

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“…Again, a higher stability of inclusion complexes with Me-β-CD formed by the IBP enantiomers with respect to racemate was revealed, in solid phase, by the combined use of FTIR-ATR spectroscopy and numerical simulation. 31 It has been ascribed to the increased difficulty, in the case of (R,S)-IBP, in breaking the intermolecular dimeric hydrogen bond between (R)-and (S)-IBP molecules, proven to constitute the first step for complexation.…”

Section: Resultsmentioning

confidence: 99%

A Phase Solubility Study on the Chiral Discrimination of Ibuprofen by β-Cyclodextrin Complexes

et al. 2011

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The effects of chiral discrimination in inclusion complexes formed by native β-cyclodextrin and its substituted form (namely methyl-β-cyclodextrin) with racemate or pure enantiomers of the non-steroidal antiinflammatory drug ibuprofen have been investigated in water. Stability constants and complexation efficiency have been determined for these host-guest systems with a 1:1 molar ratio from phase solubility profiles, showing that in aqueous solution, methylated cyclodextrin is a better complex agent than native cyclodextrin, with more enhanced effects for the (R)-enantiomer. These results have been validated using NMR technique. In particular, 1 H NMR spectra in D 2 O show a splitting of the signals for the methyl group and the aromatic protons close to the asymmetric centre of the racemate ibuprofen included in cyclodextrin cavity.

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Effect of the chiral discrimination on the vibrational properties of (R)-, (S)- and (R,S)-ibuprofen/methyl-β-cyclodextrin inclusion complexes

Cited by 13 publications

References 21 publications

Connection between the vibrational dynamics and the cross‐linking properties in cyclodextrins‐based polymers

Connection between the vibrational dynamics and the cross‐linking properties in cyclodextrins‐based polymers

Vibrational Properties of Cyclodextrin–Water Solutions Investigated by Low-Frequency Raman Scattering: Temperature and Concentration Effects

A Phase Solubility Study on the Chiral Discrimination of Ibuprofen by β-Cyclodextrin Complexes

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