Vibrational properties of ibuprofen–cyclodextrin inclusion complexes investigated by Raman scattering and numerical simulation

Rossi, Barbara; Verrocchio, P.; Viliani, G.; Mancini, Ines; Guella, Graziano; Rigo, Eveline; Scarduelli, Giorgina; Mariotto, G.

doi:10.1002/jrs.2150

Cited by 48 publications

(43 citation statements)

References 39 publications

(40 reference statements)

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“…As specified in the Introduction, and based on our previous FTIR-ATR and quantum chemical results [18,19], uncomplexed IBP prevalently develops dimeric entities derived from symmetric hydrogen bonding of the two carboxylic groups of adjacent molecules. However, as it turns out from molecular mechanics calculations and X-ray crystallographic data [3,9], in the unit cell of (S)-IBP (or (R)-IBP) the molecules in the dimer are in different conformational state, though both in the (S)-(or (R)-) configuration.…”

Section: Resultsmentioning

confidence: 99%

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

Crupi¹,

Guella²,

Majolino³

et al. 2011

Philosophical Magazine

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Effect of the chiral discrimination on the vibrational properties of (R)-, (S)-and (R, S)-ibuprofen/methyl- Effect of the chiral discrimination on the vibrational properties of (R)-, (S)-and (R, S)-ibuprofen/methyl-β β β β-cyclodextrin inclusion complexes AbstractThe effects of chiral discrimination of ibuprofen (IBP) on the complexation process with methyl-β-cyclodextrin (Me-β-CD) have been investigated, in solid phase, by FTIR-ATR spectroscopy and numerical simulation. The inclusion mechanism has been discussed by the temperature-dependent analysis of the vibrational spectra, in the C=O stretching region, of complexes formed by Me-β-CD with the two enantiomeric and the racemic forms of IBP. It turned out to be enthalpy-driven, with IBP enantiomers giving rise to more stable inclusion complexes with respect to the racemate.

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Section: Resultsmentioning

confidence: 99%

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

Crupi¹,

Guella²,

Majolino³

et al. 2011

Philosophical Magazine

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“…These changes have been interpreted on the basis of a vibrational analysis performed by both ab initio quantum chemical calculations and molecular dynamics, thereby relating such changes to the geometry of the complex, disentangling single-molecule effects from other factors, such as dimerization processes of the guest, according to a reliable methodology already successfully applied in the case of indomethacin [20,21] and ibuprofen. [22] Materials and Methods…”

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confidence: 99%

The effect of hydrogen bond on the vibrational dynamics of genistein free and complexed with β‐cyclodextrins

Crupi

Majolino

Paciaroni

et al. 2010

J Raman Spectroscopy

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Inclusion, or host-guest, complexes are supramolecular assemblies in which two or more molecules hold together and organize by means of intermolecular noncovalent bonds. In the pharmaceutical field, inclusion complexation of drugs with unsubstituted and derivative β-cyclodextrins (β-CDs) has proven to be a successful method to improve the dissolution of water insoluble drugs. Genistein (Gen), an isoflavone constituent of Onodis spinosae radix, turned out to be a suitable guest molecule for the encapsulation into β-CD, resulting in a significant improvement of its aqueous solubility. In the present study, the modifications of the vibrational spectrum of Gen caused by its inclusion into β-CDs cavity have been characterized by means of Raman scattering experiments. These changes have been interpreted by comparing the experimental data with the vibrational wavenumbers and Raman intensities obtained by simulation for the free and complexed guest molecule. Following this strategy, we have obtained a deeper understanding of the host-guest interactions involved in the formation and stabilization of the complexes, with particular regard to the role played by the guest chemical groups, as well as to disentangle the effects directly related to the complexation process from those ascribed to other factors, such as formation of intra-and intermolecular hydrogen bonds.

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“…This is in agreement with NMR data recently reported for the IBP/β-CD complex, 24 and even with those previously obtained from Raman to FTIR-ATR scattering experiments in solid phase. 22,23,25 According to the geometry of the ibuprofen/β-CD complexes as reported also by Núñez-Agüero et al 11 on the basis of structural 2D NMR experiments, we can assume that the preferred penetration mode of the guest is that where the IBP molecule is inserted in the CD cavity through its alkyl chain and aromatic ring. 20,21,26 The region corresponding to NMR signals of the aromatic protons is reported in Figure 2 Table 1 Chemical shift Δ assigned from 1 H NMR analysis in D 2 O of (R,S)-IBP to variation Δδ = δ complex − δ free observed in CD complexes (proton numbering according to Figure 1) inclusion complexes.…”

Section: Resultsmentioning

confidence: 92%

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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Vibrational properties of ibuprofen–cyclodextrin inclusion complexes investigated by Raman scattering and numerical simulation

Cited by 48 publications

References 39 publications

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

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

The effect of hydrogen bond on the vibrational dynamics of genistein free and complexed with β‐cyclodextrins

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

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