This paper describes the design and synthesis of new trehalose-type diblock methylcellulose analogues with nonionic, cationic, and anionic cellobiosyl segments, namely 1-(tri-O-methyl-cellulosyl)-4-[β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyloxymethyl]-1H-1,2,3-triazole (1), 1-(tri-O-methyl-cellulosyl)-4-[(6-amino-6-deoxy-β-d-glucopyranosyl)-(1→4)- 6-amino-6-deoxy-β-d-glucopyranosyloxymethyl]-1H-1,2,3-triazole (2), and 4-(tri-O-methyl-cellulosyloxymethyl)-1-[β-d-glucopyranuronosyl-(1→4)-β-d-glucopyranuronosyl]-1H-1,2,3-triazole (3), respectively. Aqueous solutions of all of the 1,2,3-triazole-linked diblock methylcellulose analogues possessed higher surface activities than that of industrially produced methylcellulose and exhibited lower critical solution temperatures, that allowed the formation of thermoresponsive supramolecular hydrogels at close to human body temperature. Supramolecular structures of thermo-reversible hydrogels based on compounds 1, 2, and 3 were investigated by means of scanning electron microscopy (SEM) and transmission electron microscopy (TEM). Detailed structure-property-function relationships of compounds 1, 2, and 3 were discussed. Not only nonionic hydrophilic segment but also ionic hydrophilic segments of diblock methylcellulose analogues were valid for the formation of thermo-reversible supramolecular hydrogels based on end-functionalized methylcellulose.
This paper describes a versatile pathway to heterobifunctional/telechelic cellulose ethers, such as tri-O-methyl cellulosyl azide and propargyl tri-O-methyl celluloside, having one free C-4 hydroxyl group attached to the glucosyl residue at the non-reducing end for the use in Huisgen 1,3-dipolar cycloaddition and copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The one-step end-functionalization of cellulose ethers for molecular rod synthesis involves the introduction of two reactive groups at both ends of the cellulose molecule, and can afford linear triblock copolymers via CuAAC and further reactions. We were able to tailor the degree of polymerization of end-functionalized cellulose ethers with controlled amounts of a Lewis acid, namely SnCl4. Chemical structures of the above cellulose ethers and the reaction conditions for controlling molecular length are discussed.
This paper describes the synthesis of methylcelluloses endfunctionalized with peptides and an investigation into their functions. We found that aqueous solutions of methylcellulose end-functionalized not only with carbohydrates but also with peptide segments, such as di(arginine) and di(glutamic acid), behave as thermoresponsive supramolecular hydrogelators at human-body temperature. The slow drug release from thermoresponsive hydrogels of methylcelluloses end-functionalized with peptides is attributed to ionic interactions between model drugs and peptide segments in these hydrogels. Reactions of methylated cellobiose with di(arginine) and di(glutamic acid) were used to determine optimum reaction conditions for the synthesis of methylcelluloses end-functionalized with these peptide residues). The surface activities, zeta potentials, thermal properties, hydrogelation behavior, and cytotoxicities of these peptide-functionalized methylcelluloses are also discussed. Highlights: • Methylcelluloses end-functionalized with peptides were synthesized. • Peptides-end-functionalized methylcelluloses behave as thermoresponsive supramolecular hydrogelators at human-body temperature. • The slow drug release from thermoresponsive hydrogels of methylcelluloses end-functionalized with peptides was achieved.
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