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  • Title: An Investigation into Rigidity-Activity Relationships in BisQAC Amphiphilic Antiseptics.
    Author: Kontos RC, Schallenhammer SA, Bentley BS, Morrison KR, Feliciano JA, Tasca JA, Kaplan AR, Bezpalko MW, Kassel WS, Wuest WM, Minbiole KPC.
    Journal: ChemMedChem; 2019 Jan 08; 14(1):83-87. PubMed ID: 30358105.
    Abstract:
    Twenty-one mono- and biscationic quaternary ammonium amphiphiles (monoQACs and bisQACs) were rapidly prepared in order to investigate the effects of rigidity of a diamine core structure on antiseptic activity. As anticipated, the bioactivity against a panel of six bacteria including methicillin-resistant Staphylococcus aureus (MRSA) strains was strong for bisQAC structures, and is clearly correlated with the length of non-polar side chains. Modest advantages were noted for amide-containing side chains, as compared with straight-chained alkyl substituents. Surprisingly, antiseptics with more rigidly disposed side chains, such as those in DABCO-12,12, showed the highest level of antimicrobial activity, with single-digit MIC values or better against the entire bacterial panel, including sub-micromolar activity against an MRSA strain.
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