Pharmacological performance of novel poly-(ionic liquid)-grafted chitosan-N-salicylidene Schiff bases and their complexes

• Chitosan Schiff bases bearing salicylidene ionic liquids were prepared and characterized.
• Metalation of these Schiff bases afford the corresponding Ag(I)/Pd(II) complexes (M-ILCSBs).
• The new compounds were evaluated for their in vitro antimicrobial and antitumor efficacy.
• ILCSBs and M-ILCSBs are more effective than chitosan as antimicrobial agents.
• M-ILCSBs were found to be more cytotoxic than ILCSBs.

In our endeavor to develop a new class of pharmacological candidates with antimicrobial and anticancer efficacy, a series of biopolymeric chitosan Schiff bases bearing salicylidene ionic liquid (IL-Sal) brushes (ILCSB1-3, poly-(GlcNHAc-GlcNH2-(GlcN-Sal-IL)) was successfully synthesized by adopting efficient synthetic routes. Unfortunately, metalation trials of these biopolymeric Schiff bases afford the corresponding Ag(I)/M(II) complexes (where M = Co, Pd). These designed architectures were structurally characterized and pharmacologically evaluated for their in vitro antimicrobial, against common bacterial and fungal pathogens, and anticancer activities against human colon carcinoma (HCT-116) cell line. In conclusion functionalization of chitosan with IL-Sal brushes coupled with metalation of formed ILCSBs were synergistically enhanced its antimicrobial and antitumor properties to a great extent. Noteworthy, Ag-ILCSB2 (IC50 = 9.13 μg/mL) was ca. 5-fold more cytotoxic against HCT-116 cell line than ILCSB2 (IC50 = 43.30 μg/mL).

Figure optionsDownload as PowerPoint slide