{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T07:49:05Z","timestamp":1791964145717,"version":"4.3.4"},"reference-count":36,"publisher":"Wiley","issue":"19","license":[{"start":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T00:00:00Z","timestamp":1791504000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T00:00:00Z","timestamp":1791504000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/100000060","name":"National Institute of Allergy and Infectious Diseases","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000060","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2026,10,14]]},"abstract":"<jats:p>\n                    <jats:italic>N<\/jats:italic>\n                    \u2010phenyl\u20101\u2010naphthylamine (NPN) has been widely used to probe the integrity of the outer membrane of gram\u2010negative bacteria. NPN fluoresces in the hydrophobic environment of lipid bilayers, whereas its fluorescence is quenched in the aqueous extracellular milieu. Because NPN does not intrinsically accumulate in intact gram\u2010negative bacteria, it has been broadly applied as a reporter of outer membrane permeabilization. Despite its widespread utility, systematic derivatization of this probe has remained largely unexplored. Here, we investigated the structure\u2013fluorescence relationships of NPN through the synthesis of a diverse library featuring varied linkages to the fluorogenic naphthylamine core. Subsequent library expansion was informed by density functional theory and time\u2010dependent density functional theory studies, which suggested possible origins of fluorescence quenching in aqueous environments. The final resulting library comprised 95 compounds, of which 49 exhibited a fluorogenic profile similar to that of NPN. A selected subset of analogs was then evaluated in a fluorescence\u2010based accumulation assay using varied efflux and permeation strains of\n                    <jats:italic>Escherichia coli<\/jats:italic>\n                    , revealing that installed structural motifs influenced bacterial permeation. Collectively, these probes provide a foundation for further studies examining how small structural changes affect accumulation in gram\u2010negative bacteria.\n                  <\/jats:p>","DOI":"10.1002\/cbic.70569","type":"journal-article","created":{"date-parts":[[2026,10,10]],"date-time":"2026-10-10T06:40:17Z","timestamp":1791614417000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and Fluorescence Profiling of Naphthylamine Analogs"],"prefix":"10.1002","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-9806-9360","authenticated-orcid":false,"given":"Cole M.","family":"Friederichs","sequence":"first","affiliation":[{"name":"Department of Medicinal Chemistry College of Pharmacy University of Minnesota  Minneapolis Minnesota USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-8995-0128","authenticated-orcid":false,"given":"Jackson W.","family":"Berryman","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry College of Pharmacy University of Minnesota  Minneapolis Minnesota USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Quentin M. 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