ABSTRACT
Nata de coco was chemically modified to afford the bacterial cellulose hydrogels carrying terminal alkynes. The resultant hydrogels were then converted into hydrogels carrying lactosides or those carrying α-2,3-sialyllactosides by the Cu+-catalyzed alkyne-azide cyclization. The stable homo association of the hydrogels carrying lactosides was observed in an aqueous solution containing Ca2+, thereby demonstrating the Ca2+-mediated lactoside-lactoside interactions. Ca2+ also stabilized the hetero associations among the hydrogels carrying lactosides and those carrying α-2,3-sialyllactosides, thereby also demonstrating the Ca2+-induced interactions between the lactosides and the α-2,3-sialyllactosides. The sizes of these hydrogels were of the order of ca. 5â¯mm, and their associations could thus be readily monitored with the naked eye.
Subject(s)
Cellulose/chemistry , Hydrogels/chemistry , Oligosaccharides/chemistry , Polysaccharides, Bacterial/chemistry , Alkynes/chemistry , Azides/chemistry , Calcium/chemistry , Cocos/chemistry , Cocos/microbiology , Hydrogels/chemical synthesis , Magnesium/chemistry , Plant Lectins/chemistry , Ricinus/chemistry , Sodium/chemistryABSTRACT
We synthesized phenylacetylenes containing ß-lactoside, ß-cellobioside, or ß-maltoside, and polymerized them to produce the corresponding poly (phenylacetylene)s. In these poly (phenylacetylene)s, the pendent carbohydrates were tethered to the mainchains by serinol spacers. Because similar glycosyl serinol units are found in the natural glycosphingolipids in cell membranes, the densely packed carbohydrate clusters along the poly (phenylacetylene) mainchains act as molecular mimics of cell surface glycoclusters. We analyzed the conformation of the glycosylated poly (phenylacetylene)s using circular dichroism spectroscopy, and found that the spatial carbohydrate packing within the glycoclusters changed on the addition of salts.
Subject(s)
Acetylene/analogs & derivatives , Molecular Conformation , Propanolamines/chemistry , Propylene Glycols/chemistry , Sugars/chemistry , Acetylene/chemical synthesis , Acetylene/chemistry , Chemistry Techniques, Synthetic , Glycosylation , Molecular Dynamics Simulation , Polymerization , Salts/chemistry , Stereoisomerism , Water/chemistryABSTRACT
We developed new gossypol (Gos)-based glycoconjugates through dehydration condensation of native Gos and chemically modified glycosides having aminooxy groups. The resultant glycoconjugates (glycoGos) were resistant to hydrolysis, although they were light-sensitive and slowly decomposed even under indoor lighting. The glycoGos also exhibited improved water solubility compared with native Gos, but their saturated concentrations in water were still low (6.4-17⯵M), due to their hydrophobic naphthyl rings. We also carried out WST-8 assays to assess the anticancer activity of the glycoGos on DLD-1 and HepG2 cells and found that the glycoGos having ß-lactosides and having ß-galactosides (specific ligands for asialoglycoprotein receptors) showed enhanced anticancer activity on HepG2 cells.
