title: High Efficiency Antimicrobial Thiazolium and Triazolium Side-Chain Polymethacrylates Obtained by Controlled Alkylation of the Corresponding Azole Derivatives.
abstract: Two series of antimicrobial polymethacrylates (PMTAs) bearing mono and bis-cationic quaternary ammonium cations (QUATs) were prepared by controlled N-alkylation of 1,3-thiazole and 1,2,3-triazole pendant groups with butyl iodide (PMTAs-BuI). The degree of quaternization (DQ) of the azole heterocycles was monitored by (1)H NMR spectroscopy over a wide range of reaction times. Spectra analysis of the (1)H NMR aromatic region allowed to characterize and quantify the different species involved and, therefore, to control the chemical composition distribution of the amphiphilic polycations. The polymer charge density and the hydrodynamic sizes were measured by zeta potential and dynamic light scattering (DLS), respectively. Consequently, the relationship between structure and antibacterial properties and toxicity was studied. Interestingly, these polyelectrolytes present excellent selective toxicity against bacteria being nonhemolytic even at low values of DQ. Furthermore, they were also evaluated for their microbial time-killing efficiency, presenting a 3 log-reduction in only 15 min. Additionally, the bacteria cell morphology treated with PMTAs-BuI was analyzed.
authors.affiliation: †Instituto de Ciencia y Tecnología de Polímeros (ICTP-CSIC), Juan de la Cierva 3, 28006 Madrid, Spain.
authors.forename: Rubén
authors.initials: R
authors.lastname: Tejero
authors.affiliation: †Instituto de Ciencia y Tecnología de Polímeros (ICTP-CSIC), Juan de la Cierva 3, 28006 Madrid, Spain.
authors.forename: Daniel
authors.initials: D
authors.lastname: López
authors.affiliation: ‡Hospital Universitario de Móstoles, Río Júcar, s/n, 28935 Móstoles, Madrid, Spain.
authors.forename: Fátima
authors.initials: F
authors.lastname: López-Fabal
authors.affiliation: ‡Hospital Universitario de Móstoles, Río Júcar, s/n, 28935 Móstoles, Madrid, Spain.
authors.forename: José L
authors.initials: JL
authors.lastname: Gómez-Garcés
authors.affiliation: †Instituto de Ciencia y Tecnología de Polímeros (ICTP-CSIC), Juan de la Cierva 3, 28006 Madrid, Spain.
authors.forename: Marta
authors.initials: M
authors.lastname: Fernández-García
mesh_terms: D000478:Alkylation; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011109:Polymethacrylic Acids / Q000737:chemistry*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013844:Thiazoles / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000890:Anti-Infective Agents; D011109:Polymethacrylic Acids; D013844:Thiazoles; D014230:Triazoles; C030613:polymethacrylic acid