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During the reaction optimization phase, the isolation of a mononuclear Cu(II) complex provided unique mechanistic insight into the operation of Chan\u2010Lam mono\u2010\n                    <jats:italic>N<\/jats:italic>\n                    \u2010arylation. The scope of the process is demonstrated, and then applied to access the first mono\u2010\n                    <jats:italic>N<\/jats:italic>\n                    \u2010arylated analogues of pentamidine. Sub\u2010micromolar activity against kinetoplastid parasites was observed for several analogues with no cross\u2010resistance in pentamidine and diminazene\u2010resistant trypanosome strains and against\n                    <jats:italic>Leishmania mexicana<\/jats:italic>\n                    . A fluorescent mono\u2010\n                    <jats:italic>N<\/jats:italic>\n                    \u2010arylated pentamidine analogue revealed rapid cellular uptake, accumulating in parasite nuclei and the kinetoplasts. The DNA binding capability of the mono\u2010\n                    <jats:italic>N<\/jats:italic>\n                    \u2010arylated pentamidine series was confirmed by UV\u2010melt measurements using AT\u2010rich DNA. This work highlights the potential to use Chan\u2010Lam mono\u2010\n                    <jats:italic>N<\/jats:italic>\n                    \u2010arylation to develop therapeutic leads against diamidine\u2010resistant trypanosomiasis and leishmaniasis.\n                  <\/jats:p>","DOI":"10.1002\/cmdc.202100509","type":"journal-article","created":{"date-parts":[[2021,8,6]],"date-time":"2021-08-06T09:33:40Z","timestamp":1628242420000},"page":"3396-3401","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Direct, Late\u2010Stage Mono\u2010\n                    <i>N<\/i>\n                    \u2010arylation of Pentamidine: Method Development, Mechanistic Insight, and Expedient Access to Novel Antiparastitics against Diamidine\u2010Resistant Parasites"],"prefix":"10.1002","volume":"16","author":[{"given":"Jack","family":"Robertson","sequence":"first","affiliation":[{"name":"Department of Pure and Applied Chemistry University of Strathclyde  295 Cathedral Street Glasgow G1 1XL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marzuq A.","family":"Ungogo","sequence":"additional","affiliation":[{"name":"Institute of Infection, Immunity, and Inflammation College of Medical, Veterinary, and Life Sciences University of Glasgow  Glasgow G12 8TA UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mustafa M.","family":"Aldfer","sequence":"additional","affiliation":[{"name":"Institute of Infection, Immunity, and Inflammation College of Medical, Veterinary, and Life Sciences University of Glasgow  Glasgow G12 8TA UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Leandro","family":"Lemgruber","sequence":"additional","affiliation":[{"name":"Glasgow Imaging Facility Institute of Infection, Immunity, and Inflammation College of Medical Veterinary and Life Sciences University of Glasgow  Glasgow G12 8TA UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fergus S.","family":"McWhinnie","sequence":"additional","affiliation":[{"name":"Department of Pure and Applied Chemistry University of Strathclyde  295 Cathedral Street Glasgow G1 1XL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bela E.","family":"Bode","sequence":"additional","affiliation":[{"name":"EaStCHEM School of Chemistry University of St Andrews  North Haugh St Andrews Fife KY16 9ST UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katherine L.","family":"Jones","sequence":"additional","affiliation":[{"name":"GlaxoSmithKline Medicines Research Centre  Gunnels Wood Road Stevenage Hertfordshire SG1 2NY UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Allan J. 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