Antimicrobial activity of tertiary amine covalently bonded to a polystyrene fiber

Abstract

Tertiary amine was covalently bonded to a polystyrene fiber and examined for antibacterial activity. The tertiary amine covalently bonded to a polystyrene fiber (TAF) showed a high antimicrobial activity against Escherichia coli. TAF exhibited a stronger antibacterial activity against gram-negative bacteria (E. coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhimurium, and Serratia marcescens) than against gram-positive bacteria (Staphylococcus aureus and Streptococcus faecalis) or Candida albicans. This activity against E. coli was accentuated by 0.1% deoxycholate or 10 mg of actinomycin D per ml, to which E. coli is normally not susceptible. This implies that TAF causes an increase of the bacterial outer membrane permeability. On the other hand, the antimicrobial activity was inhibited by adding Mg2+ or by lowering the pH. This suggests an electrostatic interaction between the bacterial cell wall and TAF. Scanning electron microscopy showed that E. coli cells were initially attached to TAF, with many projections on the cell surface, but then were apparently lysed after contact for 4 h. Taken together, these results imply that bacteria initially interact with TAF by an electrostatic force between the anionic bacterial outer membrane and the cationic tertiary amine residues of TAF and that longer contact with TAF damages the bacterial outer membrane structure and increases its permeability.

Isocyanate‐Free, UV‐Crosslinked Poly(Hydroxyurethane) Networks: A Sustainable Approach toward Highly Functional Antibacterial Gels

“…This is not surprising since un-quaternized tertiary amine does exhibit a certain extent of antibacterial ability. [31] For the QAC-loaded samples, the OD 625nm values of the culture media from the two materials (PHU-5% and PHU-20%) and the two bacteria were almost identical to that of the positive control. This is a clear sign of high antibacterial activity.…”

“…We hypothesized that this could be due to the inherent antibacterial properties of unmodified tertiary amines that existed throughout the network. [31]…”

(E)-2-[4-(Diethylamino)styryl]-1-methylpyridinium 4-chlorobenzenesulfonate monohydrate

“…For background to and the application of quarternary ammonium compounds as disinfectants, see: Brown & Skurray (2001); Chanawanno, Chantrapromma, Anantapong, Kanjana-Opas & Fun (2010); Domagk (1935); Endo et al (1987); Fun et al (2011); Wainwright & Kristiansen (2003). For a related structure, see: Fun et al (2011); Kaewmanee et al (2010).…”

“…Therefore, we decided to develop the novel pyridinium QACs which were expected to overcome this Staphylococcus-resistant phenomenon by modifying the QACs structures and to study their anti-MRSA activity. Among various chromophores employed in the research for chemotherapeutic drug design, tertiary amine seems to be an interesting group to be introduced into the structure (Endo et al, 1987). The title compound (I) was one among many pyridinium QACs synthesized in our laboratory (Chanawanno, Chantrapromma, Anantapong, Kanjana-Opas & Fun, 2010) hoping for a new antibacterial drug candidate and this compound showed moderate activity against MRSA with the MIC value of 150 mg/ml.…”

Potential of an antibacterial ultraviolet‐irradiated nylon film

“…The antimicrobial activity of quaternary amines and cationic antibiotics for surface disinfection and infection control, respectively, is well established with the proposed mechanism of kill involving (1) the adsorption onto the bacterial cell surface, (2) diffusion through the cell wall, (3) binding to and disruption of the cytoplasmic membrane by competing with divalent cations by forming bridges between adjacent phosphates of membrane lipids that causes release of cytoplasmic constituents such as potassium ions, DNA and RNA, and (4) eventual cell death (Bott, 1992;Endo et al, 1987;Franklin and Snow, 1989;Gale et al, 1981;Kanazawa et al, 1995). Amines have also demonstrated antimicrobial activity while bound to the surface of polystyrene fiber (Endo et al, 1987).…”