Synthesis of Gemini-Quaternary Ammonium N-Chloramine Biocides for Antibacterial Applications
A series of Gemini-quaternary ammonium(QA)N-chloramine biocides N,N-bis(3-(3-chloro-4,4-dimethyl-2,5-di-oxoimidazolidin-1-yl)propyl)-N,N,N,N-tetramethylbutane-1,4-diaminium chloride(6)～N,N-bis(3-(3-chloro-4,4-dimethyl-2,5-dioxoimidazolidin-l-yl)propyl)-N,N,N,N-tetramethyldecane-l,10-diaminiumchloride(9)with varied spacers were synthesized via ploy-step strategy started from commercial 5,5-dimethylhydantoin.The structures of precursors and corresponding N-chloramines were characterized by nuclear magnetic resonance spectroscopy(NMR)and high-resolution mass spectra(HRMS).Antibacterial activity of N-chloramines was preliminarily tested against E.coli(ATCC 25922)and S.aureus(ATCC 25923)using previous Gemini-QA N-chloramine 5 as control.Antibacterial data showed that antibacterial potency of 5～9 declined first and then increased as the spacer length increased.Specifically,9(with spacer of C10H20)demonstrated the tow-ering antibacterial capability,superior to 5～6 that exerted noticeable biocidal team effort.The greatly enhanced efficacy of 9 was probably caused by its preferable hydrophilic-lipophilic balance.It means that spacer length determines team effort bio-cidal and hydrophilic-lipophilic characteristic greatly contributes efficient contact killing.This study provides a series of effi-cacious cationic N-chloramine disinfectants,and also offers a vital reference for developing new N-chloramine antimicrobials with even higher efficacy.
Gemini-QA N-chloramineploy-step chemical synthesisantibacterial activityhydrophilic-lipophilic balancebiocidal team effort
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