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.

Poly(1,2,3-triazolium)s: a new class of functional polymer electrolytes

“…9). [77][78][79] Four neutral monomers were initially prepared by CuAAC between alkyne-functionalized methacrylates having spacers of different length and chemical nature (alkyl or succinate) and 5-(2-azidoethyl)-4-methylthiazole. FRP of these four monomers yielded polymethacrylates having M n values ranging from 50 to 100 kDa and Ð values ranging from 2.00 to 2.50 (DMF 0.1 wt% LiBr, PMMA standards).…”

Influence of spacer group on the structure and thermal properties of copolymers based on acrylonitrile and methacrylic 1,3-thiazole and 1,2,3-triazole derivatives

“…The presence of thiazole and triazole groups in the copolymeric structure permits their consequent quaternization. In our previous works [21,32] quaternized PMTA homopolymers have demonstrated high activity against bacteria and fungi without being hemotoxic. Therefore, the quaternization of these copolymers could be effective for antimicrobial applications.…”

Novel 1,2,3-triazolium-functionalized starch derivatives: Synthesis, characterization, and evaluation of antifungal property

“…The UV-vis spectra of starch derivatives bearing 1,2,3-triazole indicate broad absorption bands between 200 and 250 nm due to the presence of triazole rings and the maximum absorption values ( max ) are observed at 216-220 nm in water. However, after alkylation with iodomethane, the maximum absorption peaks shift to 225 nm, which may be ascribed to the change in electron configuration of 1,2,3-triazole caused by alkylation with iodomethane (Tejero, Lopez, Lopez-Fabal, Gomez-Garces, & Fernandez-Garcia, 2015).…”