Synthesis and Decontamination Effect on Chemical and Biological Agents of Benzoxonium-Like Salts

Abstract

Benzoxonium chloride belongs to the group of quaternary ammonium salts, which have been widely used for decades as disinfectants because of their high efficacy, low toxicity, and thermal stability. In this study, we have prepared the C10-C18 set of benzoxonium-like salts to evaluate the effect of their chemical and biological decontamination capabilities. In particular, biocidal activity against a panel of bacterial strains including Staphylococcus aureus in biofilm form was screened. In addition, the most promising compounds were successfully tested against Francisella tularensis as a representative of potential biological warfare agents. From a point of view of chemical warfare protection, the efficiency of BOC-like compounds to degrade the organophosphate simulant fenitrothion was examined. Notwithstanding that no single compound with universal effectiveness was identified, a mixture of only two compounds from this group would be able to satisfactorily cover the proposed decontamination spectrum. In addition, the compounds were evaluated for their cytotoxicity as a basic safety parameter for potential use in practice. In summary, the dual effect on chemical and biological agents of benzoxonium-like salts offer attractive potential as active components of decontamination mixtures in the case of a terrorist threat or chemical or biological accidents.

Advances in the Synthesis of Biologically Active Quaternary Ammonium Compounds

“…The more lipophilic 2c,d (C14,C16) derivatives were the most active against G+ strains, whereas G− organisms were more susceptible to slightly less hydrophobic 2b,c (C12,C14) QACs (Table 1). Cytotoxicity determined in the CHO-K1 cell line indicates that the obtained compounds are generally safe and selective; therefore, they can be potentially used in practice [36].…”

“…The more lipophilic 2c,d (C14,C16) derivatives were the most active against G+ strains, whereas G− organisms were more susceptible to slightly less hydrophobic 2b,c (C12,C14) QACs (Table 1). Cytotoxicity determined in the CHO-K1 cell line indicates that the obtained compounds are generally safe and selective; therefore, they can be potentially used in practice [36]. Jadhav et al designed and prepared a new class of heterocyclic QACs by condensation of 2-morpholinoethan-1-amine with a set of fatty acids, followed by quaternization with benzyl bromide (Scheme 3).…”

“…Scheme 2. The synthesis of benzoxonium QACs 2a-e [36]. Jadhav et al designed and prepared a new class of heterocyclic QACs by condensation of 2-morpholinoethan-1-amine with a set of fatty acids, followed by quaternization with benzyl bromide (Scheme 3).…”

Recent Trends in Protective Textiles against Biological Threats: A Focus on Biological Warfare Agents

“…Tularemia is another potential BWA [31,32]. In fact, tularemia is nowadays recognized as a reemerging disease due to the role of Francisella tularensis and its potential for misuse as a biological terrorism weapon [31,33]. This disease is caused by the Gram-negative coccobacillus-shaped bacterium F. tularensis [31,32].…”

Chemical and Biological Threats, Hazard Potential and Countermeasures

“…In summary, despite the fact that no single compound with universal effectiveness was identified, a mixture of only two compounds from this group would be able to satisfactorily cover the proposed decontamination spectrum. Furthermore, the dual effect on chemical and biological agents of benzoxonium-like salts offer attractive potential as active components of decontamination mixtures in the case of a terrorist threat or chemical or biological accidents [4]. In another work entitled 'Reactive Organic Suspensions Comprising ZnO, TiO2, and Zeolite Nanosized Adsorbents: Evaluation of Decontamination Efficiency on Soman and Sulfur Mustard' by Ginghina and Bratu, the decontamination efficiency of three types of reactive organic suspensions (based on nanosized adsorbents) on two real chemical warfare agents, soman (GD) and sulfur mustard (HD), is described.…”