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To advance our understanding of this issue, we recognized a polyaromatic structural core analogous to activators of QacR, a negative transcriptional regulator of the efflux pump QacA, and envisioned a series of quaternary ammonium compounds (QACs) based on this motif. Using commercially available dye scaffolds, we synthesized and evaluated the antimicrobial activity of 52 novel QACs bearing 1\u20133 quaternary ammonium centers. Striking differences in antimicrobial activity against bacteria bearing QAC resistance genes have been observed, with up to a 125\u2010fold increase in minimum inhibitory concentration (MIC) for select structures against bacteria known to bear efflux pumps. Based on these findings, general trends in structure\u2013resistance relationships have been identified, laying the groundwork for future mechanistic studies.<\/jats:p>","DOI":"10.1002\/cmdc.201600095","type":"journal-article","created":{"date-parts":[[2016,3,30]],"date-time":"2016-03-30T20:15:25Z","timestamp":1459368925000},"page":"958-962","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":48,"title":["Structure\u2013Resistance Relationships: Interrogating Antiseptic Resistance in Bacteria with Multicationic Quaternary Ammonium Dyes"],"prefix":"10.1002","volume":"11","author":[{"given":"Megan E.","family":"Forman","sequence":"first","affiliation":[{"name":"Department of Chemistry Villanova University  800\u2005East Lancaster Avenue Villanova PA 19085 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Madison H.","family":"Fletcher","sequence":"additional","affiliation":[{"name":"Department of Chemistry Temple University  1901\u2005North 13th Street Philadelphia PA 19122 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Megan C.","family":"Jennings","sequence":"additional","affiliation":[{"name":"Department of Chemistry Temple University  1901\u2005North 13th Street Philadelphia PA 19122 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephanie M.","family":"Duggan","sequence":"additional","affiliation":[{"name":"Department of Chemistry Villanova University  800\u2005East Lancaster Avenue Villanova PA 19085 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kevin P. 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