Synthesis and antimicrobial properties of a guanidine‐based oligomer grafted with a reactive cationic surfactant through Michael addition

Abstract

A guanidine-based oligomer grafted with a reactive cationic surfactant was designed and synthesized through Michael addition in an attempt to combine its antibacterial and emulsification properties. This was also an excellent and efficient strategy for preparing more kinds of guanidine derivatives. Fourier transform infrared spectroscopy, 1 H-NMR, and 13 C-NMR showed that the guanidine-based oligomer grafted with reactive cationic surfactant was synthesized successfully. The antimicrobial activity and antimicrobial mechanism were investigated with several approaches. The antimicrobial activity results indicated that the introduction of a cationic surfactant into the guanidine-based oligomer effectively raised the antimicrobial activity and showed a synergistic effect. The UV absorption at 260 nm was used to detect the dynamic antimicrobial process of the modified guanidine oligomer. Further, the results of scanning electron microscopy and atomic force microscopy implied that the antimicrobial mechanism of the modified guanidine oligomer changed the permeability of the cell membrane of the bacteria and caused the leakage of intracellular components of the Escherichia coli cells.

Synthesis of antibacterial polyether biguanide curing agent and its cured antibacterial epoxy resin

“…At the same time, it exchanges with cations such as Ca 2 + and Mg 2 + in the cell membrane, destroying the homeostasis of bacteria. Further, due to the thin peptidoglycan layer between the inner and outer membranes of the bacteria, the hydrophobic alkyl groups in TTB penetrate more easily penetrate the cell membrane, resulting in perforation, leakage of intracellular material, and microbial cell death [ 17 , 18 ]. The excellent antimicrobial properties of TTB may be attributed to its branched structure.…”

In Vitro and In Vivo Evaluation of the Toxic Effects of Dodecylguanidine Hydrochloride

“…Cationic active biocides, such as quaternary ammonium compounds (QACs), guanidine derivatives, and amphoteric surfactants, have been widely used for a long time. Many biocides use high binding affinity with a containing cationic group to capture negatively charged bacteria, resulting in disruption of their membrane [ 41 , 42 , 43 , 44 ]. Having a highly positively charged part is the typical chemical characteristic of guanidine-based chemicals, and it is well known that positively charged parts of chemicals can penetrate the cell membrane easily, inducing systemic toxicity in vivo [ 45 , 46 , 47 ].…”

Microwave Assisted Preparation of Antimicrobial Chitosan with Guanidine Oligomers and Its Application in Hygiene Paper Products

“…Meanwhile the primary amine groups in both chitosan and PHGC are highly reactive so that PHGC has mainly potential to be grafted onto chitosan by condensation without crosslinking agents. Works on guanidinylating modification of chitosan to enhance its antibacterial activity have been reported recently [ 14 , 15 , 26 , 31 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ]. However, only one or two guanidine groups were born in each pendent chain of the obtained guanidinylated chitosan (GCS) by applying crosslinking agents or multiple reaction procedures.…”