Effect of the structure of chitosan quaternary phosphonium salt and chitosan quaternary ammonium salt on the antibacterial and antibiofilm activity

Abstract

N-(4-N′, N′, N′-trimethylphosphonium chloride) benzoyl chitosan (TMPCS), N-(4-N′, N′, N′-triphenylphosphonium chloride) benzoyl chitosan (TPPCS), and N-(4-N′, N′, N′-trimethylmethanaminium chloride) benzoyl chitosan (TMACS) were synthesized. The structures of the products were characterized by Fourier transform infrared spectroscopy, Nuclear magnetic resonance spectroscopy and ultraviolet-visible spectroscopy. Their antibacterial activities against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) were investigated in vitro using the antibacterial rate, minimal inhibitory concentration (MIC) and minimum bactericidal concentration (MBC), the antibiofilm activity was investigated by crystal violet assay. The antibacterial assessment revealed that the chitosan quaternary phosphonium salts of similar structure had superior antibacterial activity than chitosan quaternary ammonium salt. The antibacterial rate of CS, TMPCS, TPPCS and TMACS against E. coli at 0.5 mg/mL was 10.4 %, 42.0 %, 58.5 % and 21.6 % respectively. At the same concentration, the antibacterial rate of TMPCS, TPPCS and TMACS against S.aureus was all up to 100 %. The biofilm inhibition rate of CS, TMPCS, TPPCS and TMACS at a half of MIC against E.coli was 28.4 %, 33.9 %, 56.6 % and 57.6 % respectively, and against S.aureus was 30.8 %, 53.8 %, 62.2 % and 58.5 % respectively. The biofilm removal rate of CS, TMPCS, TPPCS, TMACS against E.coli at 2.5 mg/mL was 20.6 %, 46.4 %, 48.9 % and 41.6 % respectively, and against S.aureus at 2.5 mg/mL was 41.5 %, 60.4 %, 69.9 % and 59.01 % respectively.