Physico-chemical characterization of an amphiphilic cyclodextrin/genistein complex.
Specific recognition of cell-targeting systems as host-carriers modified with receptor targeting groups, is a major ambition in the application of supramolecular science to medicine and life science. Genistein (Gen), an isoflavone belonging to the class of phytoestrogens, is of great interest because it has been considered as potential remedy for many kinds of disease. In this work, genistein in aqueous medium and in the presence of an host nanocarrier as amphiphilic cyclodextrin (CyD) modified in the upper rim with oligoethylene hydroxyl groups [(2-oligo(ethyleneoxide)-6-hexylthio)-beta-CyD, SC6OH] at 1:1 molar ratio, has been firstly investigated by UV-vis measurements coupled with circular dichroism data, in order to characterize the drug/macrocycle binding affinity through the formation of the complex. Furthermore, FTIR-ATR technique has been used to detect the complex formation in solid phase and to characterize the functional groups responsible of the solid Gen/SC6OH complex stability. The infrared absorbance spectra of the complex, collected in a wide range of wavenumber and around the physiological temperature, have been analysed and compared with the spectra of the pure compounds and their physical mixture. By monitoring the most significant changes in the shape and position of the absorbance bands of the Gen functional groups, we showed that the formation and/or modification of polar bonds play the main role in the interaction of the drug with the amphiphilic CyD. From the results, Gen is shown to be entangled in SC6OH nanoaggregates, establishing hydrogen bonding with the hydrophilic PEG chains.
Cannavà
C
C
Dipartimento Farmaco-Chimico, Università di Messina, Viale Annunziata, 98168 Messina, Italy.
Crupi
V
V
Ficarra
P
P
Guardo
M
M
Majolino
D
D
Mazzaglia
A
A
Stancanelli
R
R
Venuti
V
V
D002626:Chemistry, Pharmaceutical; D002942:Circular Dichroism; D004337:Drug Carriers; D004339:Drug Compounding; D004355:Drug Stability; D019833:Genistein / Q000737:chemistry*; D006860:Hydrogen Bonding; D049329:Nanostructures; D011092:Polyethylene Glycols / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013678:Technology, Pharmaceutical / Q000379:methods; D013696:Temperature; D047392:beta-Cyclodextrins / Q000737:chemistry*
D004337:Drug Carriers; D047392:beta-Cyclodextrins; D011092:Polyethylene Glycols; D019833:Genistein