phytoestrogens and betadex

In the present work the feasibility of β-cyclodextrin in complexation was explored, as a tool for improving the solubility and biological ability of daidzein derivatives. A series of phosphorylated daidzein derivatives featuring different chain lengths were synthesized through a modified Atherton-Todd reaction and their inclusion complexes with βCD were prepared by coprecipitation method. The inclusion complexation behavior was studied by fluorescence, UV, FT-IR, MS and (1)H NMR. The results showed that only phosphorylated daidzein derivative carrying small substituent group ((C(2)H(5)O)(2)PO) entered the cavity of βCD and formed 1:1 inclusion complex. The formation constant was 175(mol/L)(-1).

Topics: beta-Cyclodextrins; Isoflavones; Magnetic Resonance Spectroscopy; Phosphorylation; Phytoestrogens; Solubility; Spectrophotometry, Ultraviolet; Spectroscopy, Fourier Transform Infrared

Coumestrol is an estrogenic and antioxidant agent, characterized by its low solubility in aqueous and lipophilic media, once in the aglicone form. In order to improve its solubility in water, coumestrol was associated with beta-cyclodextrin in aqueous media followed by freeze-drying and characterized by SEM, (1)H NMR and molecular modeling. The analysis proved the existence of an inclusion complex, with higher probability of inclusion of the coumestrol B-ring into the wider rim of the beta-cyclodextrin molecule.

Topics: beta-Cyclodextrins; Chemistry, Physical; Coumestrol; Freeze Drying; Magnetic Resonance Spectroscopy; Microscopy, Electron, Scanning; Models, Molecular; Phytoestrogens; Solubility; Water

Inclusion complexes of cyclodextrins with nonpolar drugs are a topic of current interest in pharmaceutical science, because they increase the aqueous solubility, chemical stability and bioavailability of poorly water-soluble drugs. By means of elastic incoherent neutron scattering (EINS) technique on the backscattering spectrometer IN13, we measured, in the 150-340 K temperature range, the mean square displacements (MSD) of hydrogen atoms derived from elastic spectra of inclusion complex of beta-cyclodextrin (beta-CyD) with genistein (Gen), a phytoestrogen of great interest for its antioxidant, anticarcinogenic and antiosteoporotic activities. The mobility of the complex has been compared with the single components and the physical mixture. The elastic intensity has been interpreted in terms of the double-well model in the whole temperature range. In the case of Gen, a mainly vibrational dynamics is revealed, while for the other samples, the elastic intensity becomes non-Gaussian above a temperature T(d) congruent with 220-230 K. This dynamical activation, which is represented by an Arrhenius trend, seems to be promoted by the crystallization water molecules. The dynamics of the Gen/beta-CyD inclusion complex is restricted with respect to the physical mixture, due to the action of specific "host-guest" interactions upon complexation. Finally, the dynamical response of our systems to temperature is put in relationship with their thermal stability.

Topics: Anticarcinogenic Agents; beta-Cyclodextrins; Genistein; Phytoestrogens; Solubility; Temperature