Supramolecular hydrogels of ß-cyclodextrin linked to calcium homopoly-l-guluronate for release of coumarins with trypanocidal activity.

Association constants and thermodynamicsparameters on inclusion of four 3-amido coumarins that present trypanocidal activity, into 6-amino-ß-cyclodextrin (1:1 stoichimetry) were determined. In addition, pure homopolymeric-α-l-guluronate fraction prepared by partial hydrolysis of sodium alginate from Sub-Antarctic Kelp Durvillaea antarctica was conjugated with 6-amino-ß-cyclodextrin (64% yield). To glycoconjugates, 3-amido coumarins were incorporated (73% of encapsulation) and supramolecular hydrogels were prepared by gelation with Ca2+ ions. The trypanocidal activity of the inclusion complexes increased by 10%. Likewise, an increase in diffusion in artificial membrane was observed (13%). It was found that the inclusion complexes increased the variation of the mitochondrial potential of T. cruzi (17%). The lowest release of substituted amidocoumarins (ACS) from supramolecular hydrogels occurred at pH 1.2 whereas the maximum release (34%) was observed at pH 8.0. Encapsulation of lipophilic bioactive compounds in supramolecular hydrogels allows the generation of release systems sensitive to pH with potential application in biomedicine.

Chemical structure and biological properties of sulfated fucan from the sequential extraction of subAntarctic Lessonia sp (Phaeophyceae).

This work is related to the structural characterization of the sulfated polysaccharide from Lessonia sp and the study of its antioxidant and antiparasitic properties. Sequential extraction afforded D-mannitol as the only low MW sugar alcohol. Extraction with 2% CaCl2 afforded in 3.0% yield, a sulfated fucan (SF). Its major fraction (48.5% yield), isolated by ion-exchange chromatography corresponds to a linear polymer of α-l-fucopyranosil residues linked 1→3, sulfated at the O-4 and partially at O-2 positions. By alkaline extraction, sodium alginate (10.3% yield) was obtained. The antioxidant capacity of SF by ESR showed high elimination index (IC50, mg/mL) of hydroxyl (0.27), alkoxy (10.05), and peroxyl (82.88) radicals in relation to commercial mannitol. SF showed activity against the epimastigote form of Trypanosoma cruzi parasite (250 µg/mL) and low cytotoxicity in murine cells (367 µg/mL). The elimination capacity of radicals in aqueous medium of SF would allow its potential biomedical application.