Genistein in 1:1 Inclusion Complexes with Ramified Cyclodextrins: Theoretical, Physicochemical and Biological Evaluation

Abstract

Genistein is one of the most studied phytocompound in the class of isoflavones, presenting a notable estrogenic activity and in vitro and/or in vivo benefits in different types of cancer such as those of the bladder, kidney, lung, pancreatic, skin and endometrial cancer. A big inconvenience for drug development is low water solubility, which can be solved by using hydrophilic cyclodextrins. The aim of this study is to theoretically analyze, based on the interaction energy, the possibility of a complex formation between genistein (Gen) and three different ramified cyclodextrins (CD), using a 1:1 molar ratio Gen:CD. Theoretical data were correlated with a screening of both in vitro and in vivo activity. Proliferation of different human cancer cell lines, antimicrobial activity and angiogenesis behavior was analyzed in order to see if complexation has a beneficial effect for any of the above mentioned activities and if so, which of the three CDs is the most suitable for the incorporation of genistein, and which may lead to future improved pharmaceutical formulations. Results showed antiproliferative activity with different IC50 values for all tested cell lines, remarkable antimicrobial activity on Bacillus subtilis and antiangiogenic activity as revealed by CAM assay. Differences regarding the intensity of the activity for pure and the three Gen complexes were noticed as explained in the text. The data represent a proof that the three CDs can be used for furtherer research towards practical use in the pharmaceutical and medical field.

Effects of the Preparation Method on the Formation of True Nimodipine SBE-β-CD/HP-β-CD Inclusion Complexes and Their Dissolution Rates Enhancement

“…These results indicate that the inclusion complexes prepared by kneading exist in the new solid state, which confirms that kneading method was the best method for the preparation of inclusion complexes [30,36].…”

Physico-chemical and Biological Evaluation of Flavonols: Fisetin, Quercetin and Kaempferol Alone and Incorporated in beta Cyclodextrins

“…Thermal analysis such as differential scanning calorimetry is currently involved in cyclodextrin complexes evaluation due to the valuable information it can provide [38]. In this regard, it has been established that following the inclusion process the normal thermal behavior of the guest-molecule changes significantly as a result to its accommodation inside the cyclodextrin's cavity [33]. Analyzing the DSC profiles of the pure compounds and cyclodextrins versus the DSC profiles of the newly prepared complexes, one can notice that in all three cases the sharp peak indicating the melting point of the substance alone disappears as a result on 1:2 complexation; thus, the DSC profiles of the 1:2 products are practically identical to the curves recorded for the pure cyclodextrins.…”

“…Cyclodextrins (CD's) have been intensively used in the pharmaceutical field in order to increase the solubility, stability, safety and bioavailability of a wide range of molecules [31,32]. From the chemical point of view CD's are a family of cyclic oligosaccharides with the ability to form host-guest inclusion complexes with a wide variety of molecules, having a hydrophilic outer surface and a lipophilic central cavity.β CD's are naturally occurring CD's and contain 7 glucopyranose units [31,33].…”

Investigation of recrystallization of amorphous trehalose through hot-humidity stage X-ray powder diffraction

“…Various analytical methods are available to investigate amorphization (Jójárt-Laczkovich and Szabó-Révész, 2010; Jójárt-Laczkovich and Szabó-Révész, 2011; Danciu et al, 2014;Jug and Bećirević-Laćan, 2004), recrystallization, polymorphic conversions, and the dehydration and rehydration mechanisms of different materials (Szakonyi and Zelkó, 2012). Common techniques are differential scanning calorimetry (DSC) and X-ray powder diffraction (XRPD) measurements.…”