Characterization, solubility and biological activity of amphihilic biopolymeric Schiff bases synthesized using chitosans

•Schiff bases from chitosan, salycilaldehydes and glycidol were prepared and characterized.•1H NMR and FTIR data confirmed presence of imine and glycidol groups in the resulting structures.•Antimicrobial and antitumor activity increased for these compounds regarding chitosan itself. Chitosans are versatile biopolymers recognized for their wide range of biological activities. However, the low solubility in neutral and basic solutions restricts the applications. Thus amphiphilic biopolymeric Schiff bases from chitosans, salicylaldehyde and glycidol were successfully synthesized and characterized using 1H-NMR, UV/Vis, FTIR, TG/DTG-DTA and tested for their antimicrobial activities against plant pathogenic microorganisms and human breast cancer cells (MCF-7). Overall, functionalization of chitosans with salicylaldehyde and glycidol with different molecular weight (Mw¯) was performed to improve the biological actives of chitosans. Thus the biological activity of the new amphiphilic compounds prepared in this work were evaluated regarding microorganisms with agricultural relevance and tumor cells. The biopolymeric amphiphilic Schiff bases showed significant effects against Pseudomonas syringae (IC50 < 5 μg mL−1) compared to the natural chitosans with medium Mw¯ (CHM 223 kDa) and low Mw¯ (CHL 64 kDa), which had IC50 values of 42 and 37 μg mL−1, respectively. In addition, they improved antitumor activity against tumor cells compared to the natural chitosan.