Guest-responsive supramolecular hydrogels expressing selective sol–gel transition for sulfated glycosaminoglycans

• Published in: Polymer journal 2020-08, Vol.52 (8), p.939-946
• Main Authors: Kuroda, Naofumi, Tounoue, Yukie, Noguchi, Kouichiro, Shimasaki, Yutaro, Inokawa, Hitoshi, Takano, Masayoshi, Shinkai, Seiji, Tamaru, Shun-ichi
• Format: Article
• Language: English
• Subjects: 639/301/923/1027; 639/638/541/966; Addition polymerization; Architecture; Biomaterials; Bioorganic Chemistry; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Glycosaminoglycans; Hydrogels; Lysine; Original Article; Phase transitions; Phenylalanine; Polymer Sciences; Sol-gel processes; Stimuli; Surfaces and Interfaces; Thin Films
• ISSN: 0032-3896; 1349-0540
• DOI: 10.1038/s41428-020-0341-x

This paper describes the stimuli-responsive hydrogels constructed from bola-type amphiphiles composed of two dipeptides containing phenylalanine attached to the ends of a hydrophobic tetrathiophene. The hydrogel formation ability of the amphiphiles was affected by the N -terminal amino acid residue, which is an amphiphile-possessing phenylalanine-lysine sequence that formed a hydrogel under limited pH conditions. Gel formation occurred because of the phase transition of the gelator assembly from a granular aggregate to a fibrous architecture, in a process controlled by pH. This stimuli-responsive sol–gel transition was also accomplished by the addition of an anionic polymer, and sulfated glycosaminoglycans were successfully discriminated using the hydrogel system. A bola-type π -conjugated amphiphile containing Phe-Lys dipeptide showed a pH- and guest-induced phase transition from the granular aggregate to the fibrous architecture and formed a supramolecular hydrogel. Using this stimuli-responsiveness, the hydrogel system was successfully applied to the selective discrimination of glycosaminoglycans composed of a sulfated sugar unit.