{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,29]],"date-time":"2026-08-29T06:39:57Z","timestamp":1787985597399,"version":"build-2784847793"},"reference-count":47,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2025,5,11]],"date-time":"2025-05-11T00:00:00Z","timestamp":1746921600000},"content-version":"vor","delay-in-days":10,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2025,5]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Aiming at developing a new class of quaternary pyridinium salts, the lead compound\n                    <jats:bold>1<\/jats:bold>\n                    , characterized by a pyridine\u20103\u2010yl chalcone framework, was rationally modified by inserting alkyl functions varying from 6 to 18 carbon units. Among the set, some valuable lead compounds were identified. Derivatives\n                    <jats:bold>4<\/jats:bold>\n                    \u2013\n                    <jats:bold>6<\/jats:bold>\n                    were primarily active against\n                    <jats:italic>Staphylococcus aureus<\/jats:italic>\n                    and\n                    <jats:italic>Candida albicans<\/jats:italic>\n                    , respectively (MIC\u2009=\u20091.56 and 3.125\u2009\u03bcM). In comparison, analogs\n                    <jats:bold>4<\/jats:bold>\n                    and\n                    <jats:bold>5<\/jats:bold>\n                    showed significant activities against\n                    <jats:italic>Escherichia coli<\/jats:italic>\n                    (MIC\u2009=\u20096.25\u2009\u03bcM). Interestingly, the antimicrobial property of compounds\n                    <jats:bold>4<\/jats:bold>\n                    \u2013\n                    <jats:bold>6<\/jats:bold>\n                    , as well as their antibiofilm activity, occurred at lower concentrations than their cyto\u2010 and erythrocyte toxicities, thus ensuring a favorable safety profile. Structure\u2013activity relationship analysis highlighted the critical role of the alkyl tail length in the antimicrobial activity, and optimal results were observed for moieties ranging from 10 to 14 carbon units. Molecular dynamics studies performed on\n                    <jats:bold>2<\/jats:bold>\n                    and\n                    <jats:bold>5<\/jats:bold>\n                    by modeling them on Gram\u2010positive and Gram\u2010negative membranes showed that the derivatives, upon diffusing across periodic boundary conditions, were able to intercalate into the microbial membranes. The difference in diffusion rates provides useful information to support the diverse antimicrobial potencies of the newly designed quaternary pyridinium salt.\n                  <\/jats:p>","DOI":"10.1002\/ardp.70003","type":"journal-article","created":{"date-parts":[[2025,5,12]],"date-time":"2025-05-12T02:40:55Z","timestamp":1747017655000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Alkyl Tail Variation on Chalcone\u2010Based Quaternary Pyridinium Salts as Rule\u2010of\u2010Thumb for Antimicrobial Activity"],"prefix":"10.1002","volume":"358","author":[{"given":"Francesca","family":"Seghetti","sequence":"first","affiliation":[{"name":"Department of Pharmacy and Biotechnology Alma Mater Studiorum\u2010University of Bologna Bologna Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Riccardo","family":"Ocello","sequence":"additional","affiliation":[{"name":"Department of Pharmacy and 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