Preparation, characterization, and antibacterial property of carboxymethyl cellulose derivatives bearing tetrabutylammonium salt

Abstract

Carboxymethyl cellulose derivatives bearing tetrabutylammonium moieties (CMC-TBA) were synthesized by the acidification of carboxymethyl cellulose (CMC) followed by acid-base neutralization with tetrabutylammonium hydroxide. The products were identified by Fourier transform infrared (FT-IR), ¹H nuclear magnetic resonance (NMR) spectroscopy and the degrees of substitution (DS) values were also quantified according to the integral area values in ¹H NMR spectra. It was revealed that DS values had a positive relationship with the molar ratios of TBAOH to CMC. The antibacterial behaviors against gram-positive bacteria S. aureus and gram-negative bacteria E. coli were investigated using serial two-fold dilution method (MIC and MBC) and the disc diffusion method (inhibition zone). The results showed that comparison with CMC, all new CMC-TBA derivatives exhibited high antibacterial activity that depends on bacteria type and their degrees of cationization. The antibacterial action was more effective against S. aureus than E. coli, which could be attributed to the fact that the latter has a complicated bilayer structure of cell wall. Besides, an apparent tendency that the antibacterial activity of CMC-TBA derivatives enhanced with an increase in the degrees of cationization was found. This work suggests that these new derivatives can be introduced as efficient antibacterial biomaterials for biomedical purposes.

Keywords: Antibacterial activity; Carboxymethyl cellulose; Carboxymethyl cellulose derivatives; Organic acid-base neutralization; Tetrabutylammonium salt.