An injectable supramolecular antimicrobial hydrogel based on hyaluronic acid with dynamic borate bond and hydrogen bond crosslinking for sinusitis treatment

Abstract

In this study, chlorogenic acid-modified hyaluronic acid (HA-CGA) and phenylboric acid-modified ciprofloxacin (Cip-BPA) were synthesized and their structures were analyzed by ¹HNMR and ¹³CNMR. Following, a dynamic borate and hydrogen bond crosslinked HCCB hydrogel was prepared by mixing HA-CGA and Cip-BPA solution. Its properties and gel formation mechanism were studied by means of ratio optimization, scanning electron microscopy, rheology, ¹¹B-NMR and temperature-changing infrared spectroscopy. The basic properties and bioactivity of HCCB hydrogel were investigated by in vitro antibacterial experiment, in vitro anti-inflammatory oxidation experiment and biocompatibility test. We found that borate ester bond and hydrogen bond are important driving forces for the formation of HCCB hydrogels, and when the molar ratio of chlorogenic acid in HA-CGA and phenylboronic acid in Cip-BPA is 2:1, the properties of HCCB hydrogels formed are the best. It has excellent antibacterial properties, anti-inflammatory and antioxidant properties, good biocompatibility and pH/ROS response. The successful preparation of the gel and its excellent properties indicate that it has great potential in the treatment of some inflammation treatment.