Biologically active polymers. IV. Synthesis and antimicrobial activity of tartaric acid polyamides

Abstract

New bactericidal polyamides with quaternary ammonium or phosphonium salts were prepared, and their antimicrobial activities were explored. The polyamides were synthesized by the polycondensation of diethyl-l-tartrate or chloromethylated diethyl-l-tartrate with ethylenediamine in dry absolute ethanol. The polyamides were modified to yield polymers with either quaternary ammonium or phosphonium salts. The polymers were characterized with elemental microanalysis and 1 H-NMR and IR spectra. The antimicrobial activity of the polymers bearing onium salts was studied against Gram-negative bacteria (Escherichia coli, Pseudomones aeruginosa, Shigella sp., and Salmonella typhae), Gram-positive bacteria (Bacillus subtilis and Bacillus cereus), and a fungus (Trichophytum rubrum) by the cut-plug and viable-cell-count methods. Although all the polymers showed high antibacterial activity, some had no antifungal activity. The tributyl phosphonium salt of the polyamide was more effective against both Gram-negative and Gram-positive bacteria than the triethyl ammonium and triphenyl phosphonium salts of the polyamide.

Antimicrobial activities and mode of action of the selected novel thienopyrimidines derivatives 2-[2-(diphenylmethylene) hydrazino]-5-isopropyl-3-methylthieno [2, 3-d] pyrimidin-4-one

“…Other researchers found that cyclopenteno and cyclohexeno (31) coincide with that of the compound no.20 in this study. They found that the growth inhibitory effect M/C of polymer IX became stronger in the order of B. subtilis<E. coli <P. aeruginosa< a fungus (Trichophyton rubrum).…”

Controlling macromolecular structures towards effective antimicrobial polymers

“…It is interpreted in terms of a sequence of essential processes [35]: (1) It initiates by the adsorption on microbial cell surface. This utmost important step is also the basis of selectivity towards microbes; (2) Then the polycations diffuse through the cell wall and/or (3) interact with the cytoplasmic membrane; (4) This interaction may irreversibly damage the integrity of the cell membrane; (5) subsequently result in the release of cytoplasmic components including K þ ions, DNA/RNA; and (6) finally lead to cell death.…”

Infectious disease: Connecting innate immunity to biocidal polymers

“…Kenawy and coworkers have also developed several routes to access quaternary ammonium or phosphonium salts on a polymethacrylate [86] or a polyamide, 21, backbone [87]. For both series, the polymer with the tributyl phosphonium salt was observed to be the most effective against bacteria and fungi.…”

“…21 = Ammonium and phosphonium polymers synthesized from a common reactive backbone [87]. 22 = Polystyrenes with quaternary ammonium groups [8,88].…”