Amphiphilic Cyclodextrins as Nanocarriers of Genistein: A Spectroscopic Investigation Pointing Out the Structural Properties of the Host/Drug Complex System

Stancanelli, Rosanna; Guardo, M.; Cannavà, Carmela; Guglielmo, Giovanni; Ficarra, P.; Villari, Valentina; Micali, Norberto; Mazzaglia, Antonino

doi:10.1002/jps.22065

Cited by 22 publications

(11 citation statements)

References 34 publications

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“…The complexes of genistein with the natural beta-cyclodextrin proved a higher solubility and bioavailability compared to the drug alone [16]. Considering the rather low water solubility of natural β-CD, studies have been conducted on the complexation of genistein with derivatisedcyclodextrins [17]. To the best of our knowledge, no studies have been performed on the biological properties (i.e.…”

Section: Resultsmentioning

confidence: 99%

“…In case of the complex genisten : HPBCD, Figure 7d, haematoxylin-eosin (H&E) analysis detected a rich polymorphous inflammatory infiltrate that increased in thickness the sub epithelial dermis without the presence of an inflammatory infiltrate in the epithelial tissue, while in case of the complex genistein : RAMEB, Figure 7e, H&E analysis detected an epithelial and cartilaginous tissue with marked oedema. Inclusion complexes of cyclodextrins with nonpolar drugs represent a topic of high interest in pharmaceutical research, for providing the possibility to increase the water solubility, stability and bioavailability of the guest drugs [14,17,28,29]. Genistein bioavailability can be increased by complexation with CDs [30].…”

Section: Resultsmentioning

confidence: 99%

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Changes in the anti-inflammatory activity of soy isoflavonoid genistein versus genistein incorporated in two types of cyclodextrin derivatives

Danciu

Şoica

Csányi

et al. 2012

Chemistry Central Journal

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BackgroundThe isoflavonoid genistein represents the major active compound from soybean, the vegetal product from Glycine max (Fabaceae). The aim of this study is to prove that genistein was incorporated in two semisynthetic cyclodextrins, beta-cyclodextrin derivatives: hydroxypropyl-beta-cyclodextrin and randomly-methylated-beta-cyclodextrin as well as to compare the anti-inflammatory activity of genistein with that of genistein incorporated in these two types of semisynthetic cyclodextrins.ResultsThe animal studies were conducted on 8-week old C57BL/6 J female mice. Inflammation was induced in both ears of each mouse by topical application of 10 micrograms 12-O-tetradecanoylphorbol-3-acetate dissolved in 0.1 ml solvent (acetone : dimethylsulfoxide in a molar ratio 9:1). Thirty minutes later treatment was applied. The inflammatory reaction was correlated with increased values in ear thickness. Treatment with genistein and genistein incorporated in the two cyclodextrins led to decreased values for ear thickness. Better anti-inflammatory action was found for the complexes of genistein. Both haematoxylin-eosin analysis and CD45 marker expression are in agreement with these findings.ConclusionsResults allow concluding that genistein is an active anti-inflammatory phytocompound and its complexation with hydrophilic beta-cyclodextrin derivatives leads to a stronger anti-inflammatory activity.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Changes in the anti-inflammatory activity of soy isoflavonoid genistein versus genistein incorporated in two types of cyclodextrin derivatives

Danciu

Şoica

Csányi

et al. 2012

Chemistry Central Journal

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“…Another study on b-CD PEGylated (Box 3) on the wide rim and grafted with alkyl chains on the narrow rim indicated that NP size decreased with increasing alkyl chains (from 140 nm for C 6 to 95 nm for C 16 ) [33,34]. However, the encapsulation of genistein, which is a hormone studied in prostate cancer treatment, or docetaxel, which is a well-known anticancer agent, in these NPs did not influence their size [33,34]. Furthermore, chain length can influence the type of supramolecular assembly because it increased the size of the hydrophobic part; the hydrophilic lipophilic balance (HLB) is modified, thus increasing the size of NPs.…”

Section: Q4mentioning

confidence: 98%

Cyclodextrin nanoassemblies: a promising tool for drug delivery

Bonnet

Gervaise

Djedaïni‐Pilard

et al. 2015

Drug Discovery Today

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“…In the recent past, the aggregation behavior of aCD was investigated in water, getting insights on the structures of free nanoassemblies [ 5 – 6 ] or in combination with therapeutic agents [ 7 ]. However, in some stages of preparation and investigation of nanoconstructs based on aCD, the dissolution in organic nonpolar solvent is mandatory to prepare stable nanoemulsions [ 4 , 8 ], thin films [ 9 ] or organic dispersions for spectroscopic characterization of aCD unimers [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Aggregation behavior of amphiphilic cyclodextrins in a nonpolar solvent: evidence of large-scale structures by atomistic molecular dynamics simulations and solution studies

Raffaini

Mazzaglia

2016

Beilstein J. Org. Chem.

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SummaryChemically modified cyclodextrins carrying both hydrophobic and hydrophilic substituents may form supramolecular aggregates or nanostructures of great interest. These systems have been usually investigated and characterized in water for their potential use as nanocarriers for drug delivery, but they can also aggregate in apolar solvents, as shown in the present paper through atomistic molecular dynamics simulations and dynamic light scattering measurements. The simulations, carried out with a large number of molecules in vacuo adopting an unbiased bottom-up approach, suggest the formation of bidimensional structures with characteristic length scales of the order of 10 nm, although some of these sizes are possibly affected by the assumed periodicity of the simulation cell, in particular at longer lengths. In any case, these nanostructures are stable at least from the kinetic viewpoint for relatively long times thanks to the large number of intermolecular interactions of dipolar and dispersive nature. The dynamic light scattering experiments indicate the presence of aggregates with a hydrodynamic radius of the order of 80 nm and a relatively modest polydispersity, even though smaller nanometer-sized aggregates cannot be fully ruled out. Taken together, these simulation and experimental results indicate that amphiphilically modified cyclodextrins do also form large-scale nanoaggregates even in apolar solvents.

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Amphiphilic Cyclodextrins as Nanocarriers of Genistein: A Spectroscopic Investigation Pointing Out the Structural Properties of the Host/Drug Complex System

Cited by 22 publications

References 34 publications

Changes in the anti-inflammatory activity of soy isoflavonoid genistein versus genistein incorporated in two types of cyclodextrin derivatives

Changes in the anti-inflammatory activity of soy isoflavonoid genistein versus genistein incorporated in two types of cyclodextrin derivatives

Cyclodextrin nanoassemblies: a promising tool for drug delivery

Aggregation behavior of amphiphilic cyclodextrins in a nonpolar solvent: evidence of large-scale structures by atomistic molecular dynamics simulations and solution studies

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