Radical Scavenging Activities of Novel Cationic Inulin Derivatives

Many saccharides are attractive targets for biomaterial applications, due to their abundance, biocompatibility, and biodegradability. In this article, a synthesis process of 6-N-substituted cationic inulin derivatives, including 6-pyridyl-6-deoxyinulin bromide (PIL), 6-(2-amino-pyridyl)-6-deoxyinulin bromide (2APIL), 6-(3-amino-pyridyl)-6-deoxyinulin bromide (3APIL), 6-(4-amino-pyridyl)-6-deoxyinulin bromide (4APIL), 6-(2,3-diamino-pyridyl)-6-deoxyinulin bromide (2,3DAPIL), 6-(3,4-diamino-pyridyl)-6-deoxyinulin bromide (3,4DAPIL), and 6-(2,6-diamino-pyridyl)-6-deoxyinulin bromide (2,6DAPIL) was described. The C(6)-OH of inulin was first activated by PPh(3)/N-bromosuccinimide (NBS) bromination. Then, pyridine and different kinds of amino-pyridine groups (different position and different numbers of amino) were grafted onto inulin, respectively, via nucleophilic substitution. Then, we confirmed their structure by Fourier transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance (NMR) spectroscopy. After this, their radical scavenging activities against hydroxyl radical and diphenylpicryl phenylhydrazine (DPPH) radical were tested in vitro. Each derivative showed a distinct improvement in radical scavenging activity when compared to inulin. The hydroxyl-radical scavenging effect decreased in the following order: 3APIL > PIL > 3,4DAPIL > 4APIL > 2,3DAPIL > 2,6DAPIL > 2APIL. Amongst them, 3APIL revealed the most powerful scavenging effect on hydroxyl radicals, as well as DPPH radicals. At 1.6 mg/mL, it could completely eliminate hydroxyl radicals and could clear 65% of DPPH radicals. The results also showed that the steric hindrance effect and the substitute position of the amino group had an effect on the radical scavenging activity. Moreover, the application prospects of inulin derivatives as natural antioxidant biomaterials are scientifically proven in this paper.