UV–vis and FTIR–ATR spectroscopic techniques to study the inclusion complexes of genistein with β-cyclodextrins

Crupi, V.; Ficarra, R.; Guardo, M.; Majolino, D.; Stancanelli, Rosanna; Venuti, Valentina

doi:10.1016/j.jpba.2007.01.054

Cited by 105 publications

(63 citation statements)

References 32 publications

(29 reference statements)

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“…This linear increase (r 2 > 0.99) in GEN solubility classifies the phase-diagram as A L type, as already observed by Crupi et al. 7 The apparent stability constant determined for the GEN/β-CD complex was 3492 ± 769 mol L -1 and suggests a relatively strong interaction between both molecules.…”

Section: Lc Methods Validationsupporting

confidence: 82%

“…However, its activities are conditioned to the aglicone form, which presents reduced aqueous solubility. 7,8 This fact limits its application in the pharmaceutical field and the complexation of this isoflavone with cyclodextrins (CDs) has emerged as an interesting alternative for the improvement of GEN aqueous solubility. CDs are cyclic oligosaccharides consisting of variable glucopyranose units linked by a-(1,4) bonds, with relative water solubility.…”

Section: Introductionmentioning

confidence: 99%

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Improvement of genistein content in solid genistein/-cyclodextrin complexes β

et al. 2010

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Recebido em 17/3/09; aceito em 7/9/09; publicado na web em 23/2/10 Genistein:β-cyclodextrin complexes with high drug loading (19.22%) were prepared by freeze-drying and characterized by differential scanning calorimetry and hydrogen nuclear magnetic resonance spectroscopy. The spatial configuration of the complex was proposed by means of 2D-NOESY experiment combined with molecular modeling. According to the results obtained, the interaction of genistein with β-cyclodextrin in a 1:1 complex is supposed to occur mainly through the insertion of the guest A-ring in cyclodextrin cavity, without rule out the possibility of inclusion through the B-ring, as previously reported in the literature.

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Section: Lc Methods Validationsupporting

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Improvement of genistein content in solid genistein/-cyclodextrin complexes β

et al. 2010

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“…[25] stress that in the range 4,000-2,000 cm −1 genistein presents an absorption band at approximately 3,405 cm -1 , normally attributed to the O-H stretching vibration, overlapped with a band located at 3,084 cm -1 attributed to C-H stretching vibration. In the presented case, the broad band located at over 3,000 cm -1 could be assigned for this kind of vibrational behaviour.…”

Section: Discussionmentioning

confidence: 83%

Total phenolic content, FTIR analysis, and antiproliferative evaluation of lupin seeds harvest from western Romania

Danciu¹,

Pavel²,

Băbuţa³

et al. 2017

Ann Agric Environ Med.

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, also known as white lupin, Lupinus angustifolius L., and narrowleafed lupin or blue lupin, represent two of the most studied species due to their intense culinary use and potential biological activity. The intention of the study was to characterize total phenolic content, perform FTIR analysis, and antiproliferative effects against A375 human melanoma cells extracts obtained from germinated and ungerminated seeds from Lupinus albus L. and Lupinus angustifolius L. Materials and method. Total phenolic content was assessed using the FolinCiocalteu colorimetric method. FTIR spectra were carried out by a Shimadzu Prestige21 spectrometer in the range 400-4000 cm

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“…[15,16] In a previous study, [17] we investigated, in pure water, the effect of complexation of unsubstituted and derivative β-CDs on the UV absorption of Gen. A phase-solubility study allowed us to evaluate the changes of isoflavone in the complexation state, suggesting that it forms complexes with a stoichiometry of 1 : 1. Then, Fourier transform infrared spectroscopy in the attenuated total reflectance geometry (FTIR-ATR) has been successfully used to put into evidence the host-guest interactions at the molecular level in solid phase.…”

mentioning

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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UV–vis and FTIR–ATR spectroscopic techniques to study the inclusion complexes of genistein with β-cyclodextrins

Cited by 105 publications

References 32 publications

Improvement of genistein content in solid genistein/-cyclodextrin complexes β

Improvement of genistein content in solid genistein/-cyclodextrin complexes β

Total phenolic content, FTIR analysis, and antiproliferative evaluation of lupin seeds harvest from western Romania

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

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