{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,17]],"date-time":"2026-09-17T18:55:03Z","timestamp":1789671303482,"version":"4.0.1"},"reference-count":42,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,6,3]],"date-time":"2026-06-03T00:00:00Z","timestamp":1780444800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,6,3]],"date-time":"2026-06-03T00:00:00Z","timestamp":1780444800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE\u20102304883"],"award-info":[{"award-number":["CHE\u20102304883"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"abstract":"ABSTRACT<\/jats:title>\n \n We investigated inclusion complexation of levamisole (LEV\n +<\/jats:sup>\n ), a common adulterant of cocaine (COC\n +<\/jats:sup>\n ), with six molecular baskets\n 1<\/jats:bold>\n 3\u2212<\/jats:sup>\n \u20136<\/jats:bold>\n 18\u2212<\/jats:sup>\n of increasing cavity depth and anionic charge at the portal.\n 1<\/jats:sup>\n H NMR and mass spectrometry showed that\n 1<\/jats:bold>\n 3\u2212<\/jats:sup>\n to\n 6<\/jats:bold>\n 18\u2212<\/jats:sup>\n bind to LEV\n +<\/jats:sup>\n to form binary complexes in water, with the stability increasing across the series and highest for dendritic basket\n 6<\/jats:bold>\n 18\u2212<\/jats:sup>\n (\n K<\/jats:italic>\n d<\/jats:sub>\n = 10 \u00b5M). From\n 1<\/jats:sup>\n H NMR magnetic shielding and OPLS4 calculations, we deduced that LEV\n +<\/jats:sup>\n inserts its benzene in the binding pocket of\n 1<\/jats:bold>\n 3\u2212<\/jats:sup>\n \u2013\n 6<\/jats:bold>\n 18\u2212<\/jats:sup>\n while the protonated heterocycle remains near the anionic portal. The stability of [LEV\u2282\n 6<\/jats:bold>\n ]\n 17\u2212<\/jats:sup>\n arises from C\u2212H\n \u2026<\/jats:sup>\n \u03c0\/cation\n \u2026<\/jats:sup>\n \u03c0\/\u03c0\u2212\u03c0 contacts, ion pairing, and hydrophobic effect (\u0394\n H\u00b0<\/jats:italic>\n <\u00a00, ITC). Dendritic basket\n 6<\/jats:bold>\n 18\u2212<\/jats:sup>\n was subsequently used to develop a fluorescent displacement assay (FDA) for the detection of LEV\n +<\/jats:sup>\n with alizarin red S (ALZ\n \u2212<\/jats:sup>\n ) as a fluorescence reporter. LEV\n +<\/jats:sup>\n displaced the dye to generate a fluorescence response suitable for its detection in water over circa 10\u2013300 \u00b5M range. In contrast, COC\n +<\/jats:sup>\n bound more strongly to basket\n 6<\/jats:bold>\n 18\u2212<\/jats:sup>\n , forming binary (\n K<\/jats:italic>\n d<\/jats:sub>\n = 1 \u00b5M) and ternary complexes (\n 1<\/jats:sup>\n H NMR, calorimetry, and FDA). The binding mode of COC\n +<\/jats:sup>\n differs from that of LEV\n +<\/jats:sup>\n , with the drug's cationic fragment occupying the basket's cavity.\n <\/jats:p>","DOI":"10.1002\/chem.71216","type":"journal-article","created":{"date-parts":[[2026,6,4]],"date-time":"2026-06-04T04:10:28Z","timestamp":1780546228000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Inclusion Complexations of Levamisole and Cocaine With Molecular Baskets. Fluorescence Displacement Assay for Detection of Cocaine and Its Adulterant Levamisole in Aqueous Media"],"prefix":"10.1002","author":[{"given":"Christopher T.","family":"Mortensen","sequence":"first","affiliation":[{"name":"Department of Chemistry & Biochemistry The Ohio State University Columbus Ohio USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carson E.","family":"Ward","sequence":"additional","affiliation":[{"name":"Department of Chemistry & Biochemistry The Ohio State University Columbus Ohio USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nitesh","family":"Kumar","sequence":"additional","affiliation":[{"name":"Department of Chemistry & Biochemistry The Ohio State University Columbus Ohio USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Logan","family":"Willemann","sequence":"additional","affiliation":[{"name":"Department of Chemistry & Biochemistry The Ohio State University Columbus Ohio USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryan","family":"Lutz","sequence":"additional","affiliation":[{"name":"Department of Chemistry & Biochemistry The Ohio State University Columbus Ohio USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kailey","family":"Hughes","sequence":"additional","affiliation":[{"name":"Department of Chemistry & Biochemistry The Ohio State University Columbus Ohio USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zheng","family":"Zheng","sequence":"additional","affiliation":[{"name":"Department of Chemistry & Biochemistry The Ohio State University Columbus Ohio USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7540-2387","authenticated-orcid":false,"given":"Jovica D.","family":"Badji\u0107","sequence":"additional","affiliation":[{"name":"Department of Chemistry & Biochemistry The Ohio State University Columbus Ohio USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,6,3]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1476\u20105381.1970.tb10601.x"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1056\/NEJM199002083220602"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1111\/bcp.15037"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.2460\/javma.23.06.0340"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.neuint.2013.11.010"},{"key":"e_1_2_7_7_1","doi-asserted-by":"crossref","first-page":"408","DOI":"10.1038\/clpt.2010.156","article-title":"A Dangerous New Cocaine Adulterant","volume":"88","author":"Chang A. 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