Synthesis and Antimicrobial Evaluation of Bis‐morpholine Triazine Quaternary Ammonium Salts

Abstract

Efficient, environmentally and economically sustainable, and nontoxic antibacterial products are of global relevance in the fight against microorganism contamination. In this work, an easy and straightforward method for the synthesis of bis‐morpholino triazine quaternary ammonium salts (bis‐mTQAS) is reported, starting from 2,4,6‐trichloro‐1,3,5‐triazine or 2,4‐dichloro‐6‐methoxy‐1,3,5‐triazine and various N‐alkylmorpholines. Bis‐mTQAS were tested as antimicrobials against Gram‐negative and Gram‐positive bacterial strains. The best‐performing bis‐mTQAS were found to achieve total disinfection against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 at 50 and 400 μg/mL, respectively. Distinctively, bis‐mTQAS with the highest antimicrobial efficiency had lowest cytotoxicity.

Unusual Boronium Salt Shows Antifungal Activity Comparable to a Commercial Quaternary Ammonium Disinfectant

“…A new report by Morandini, et. al [15] . on the synthesis and antimicrobial activity of a bis morpholine triazine quaternary ammonium salt (bis‐mTQAS) may shed light on potential bacterial inhibition mechanisms for the BIN and BIT boronium ion variants.…”

“…The antibacterial effectiveness of QAC compounds appears to be related to their ability to alter bacterial cell wall structure‐function relationships and electrostatically interact with negatively charged polar head groups of plasma membranes phospholipids [16] . An efficient antimicrobial QAC is said to require a hydrophobic chain and a hydrophilic head [15] . In this respect, QAC efficacy is related to the possession of a hydrophobic “tail” (alkyl chain), being similar in structure to those seen embedded in plasma membrane bilayers.…”

“…al. [15] on the synthesis and antimicrobial activity of a bis morpholine triazine quaternary ammonium salt (bis-mTQAS) may shed light on potential bacterial inhibition mechanisms for the BIN and BIT boronium ion variants. Their study group challenged both gram-positive Staphylococcus aureus (ATCC 25923) and gram-negative Escherichia coli (ATCC 25922) with several derived bis-mTQAS compounds of various alkyl chain ranging from 8 to 16-C in length.…”

“…[16] An efficient antimicrobial QAC is said to require a hydrophobic chain and a hydrophilic head. [15] In this respect, QAC efficacy is related to the possession of a hydrophobic "tail" (alkyl chain), being similar in structure to those seen embedded in plasma membrane bilayers. Tails are thought to interdigitate themselves in outer phospholipid layer and subsequently release them from the underlying membrane surface.…”

Insight in triazine chromatographic and microbiological analysis: A brief review

“…It has been found that his complex shows significant antimicrobial effects on the tested microorganisms. Morandini et al conducted research where antibacterial assay of the bis-morpholine triazine quaternary ammonium salts (bis-mTQAS) was evaluated (39). These bis-mTQAS were tested for their antibacterial activity against one gram-positive (S. aureus) and one gram-negative bacterial strain (E. coli).…”