Abstract
The development of organic polymer materials for disinfection and sterilization is thought of as one of the most promising avenues to solve the growth and spread of harmful microorganisms. Here, a series of linear polyisocyanide quaternary ammonium salts (L-PQASs) with different structures and chain lengths were designed and synthesized by polymerization of phenyl isocyanide monomer containing a 4-chloro-1-butyl side chain followed by quaternary amination salinization. The resultant compounds were characterized by 1H NMR and FT-IR. The antibacterial activity of L-PQASs with different structures and chain lengths against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) was evaluated by determining the minimum inhibitory concentrations (MICs). The L-POcQAS-M50 has the strongest antimicrobial activity with MICs of 27 μg/mL against E. coli and 32 μg/mL against S. aureus. When the L-PQASs had the same polymerization degree, the order of the antibacterial activity of the L-PQASs was L-POcQAS-Mn > L-PBuQAS-Mn > L-PBnQAS-Mn > L-PDBQAS-Mn (linear, polyisocyanide quaternary ammonium salt, monomer, n = 50,100). However, when L-PQASs had the same side chain, the antibacterial activity reduced with the increase of the molecular weight of the main chain. These results demonstrated that the antibacterial activity of L-PQASs was dependent on the structure of the main chain and the length of the side chain. In addition, we also found that the L-POcQAS-M50 had a significant killing effect on MK-28 gastric cancer cells.
Highlights
Nowadays, microbial infection is still a heavy threat to public health worldwide.Especially the common bacteria in the environment seriously endanger human health all the time [1,2]
Quaternary ammonium salts (QASs) are a class of extensively studied materials owing to its long-term antibacterial property, low toxicity, low permeability, and excellent safety [6]
Linda et al developed a series of quaternary ammonium compounds (QACs) derived from quinuclidin-3-ol and an alkyl chain of variable length, and found that it is necessary for new compounds to get better antimicrobial potentials by the addition of alkyl chains containing at least ten carbon atoms [16]
Summary
Microbial infection is still a heavy threat to public health worldwide. Especially the common bacteria in the environment seriously endanger human health all the time [1,2]. QASs show the advantages of designable molecular structure, high functionality, no volatility, prolonged lifetime, and chemical stability [7,8,9] They have been extensively applied in the fields of antibacterial and antitumor materials [10,11,12]. Stoikova et al designed new bactericidal and antibacterial agents based on QACs on thiacalixarene macrocyclic platform. These agents exhibited high antibacterial effect [17]. It is a feasible strategy to develop new QAS materials with excellent antimicrobial and antitumor activity by changing their structures and chain lengths. We investigated the killing effect of the L-POcQAS-M50 on MK-28 gastric cancer cells
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