{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T13:37:56Z","timestamp":1790689076242,"version":"4.1.0"},"reference-count":34,"publisher":"Wiley","issue":"54","license":[{"start":{"date-parts":[[2018,9,5]],"date-time":"2018-09-05T00:00:00Z","timestamp":1536105600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100000038","name":"Natural Sciences and Engineering Research Council of Canada","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000038","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2018,9,25]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Zn<jats:sup>II<\/jats:sup> concentrations in malignant prostate tissues are much lower than in benign or healthy, suggesting that Zn<jats:sup>II<\/jats:sup> levels are a potential biomarker for prostate cancer (PCa). Five 2,2\u2032\u2010bipyridine ligands were synthesized containing amino substituents with varying electron\u2010donating ability for investigation as fluorescent Zn<jats:sup>II<\/jats:sup> indicators. The excited state characteristics of the ligands were explored by UV\/Vis and fluorescence spectroscopy. 3,3\u2032\u2010Diamino\u20102,2\u2032\u2010bipyridine\u2005(<jats:bold>1<\/jats:bold>) was previously shown to be weakly fluorescent as a result of \u03c0\u2192\u03c0* transitions. The other four ligands have properties consistent with an n\u2192\u03c0* intraligand charge transfer excited state. Strongly donating amino and aminophenyl\u2005(<jats:bold>2<\/jats:bold> and <jats:bold>4<\/jats:bold>) substituents gave low quantum yields, while weaker donating benzimidazole substituents\u2005(<jats:bold>6<\/jats:bold> and <jats:bold>7<\/jats:bold>) gave high quantum yields. Absorption and fluorescence wavelengths underwent bathochromic shifts upon Zn<jats:sup>II<\/jats:sup> binding in a majority of cases. Quantum yields drastically increased upon Zn<jats:sup>II<\/jats:sup> binding for <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold>, but decreased for <jats:bold>4<\/jats:bold>, <jats:bold>6<\/jats:bold>, and <jats:bold>7<\/jats:bold>. Compounds\u2005<jats:bold>6<\/jats:bold> and <jats:bold>7<\/jats:bold> were incubated with PC\u20103, DU 145 and BPH\u20101 cells to determine their Zn<jats:sup>II<\/jats:sup> sensing abilities in a biological system. Weak fluorescence was observed in BPH\u20101 cells and subsequent incubation with Zn<jats:sup>II<\/jats:sup> caused fluorescence intensity to increase. No fluorescence was observed in PCa cell lines. Further investigation of these ligands may allow for quantitative determination of Zn<jats:sup>II<\/jats:sup> concentrations in ex vivo tissue samples.<\/jats:p>","DOI":"10.1002\/chem.201803051","type":"journal-article","created":{"date-parts":[[2018,7,26]],"date-time":"2018-07-26T21:45:55Z","timestamp":1532641555000},"page":"14539-14546","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Amino\u2010Substituted 2,2\u2032\u2010Bipyridine Ligands as Fluorescent Indicators for Zn<sup>II<\/sup> and Applications for Fluorescence Imaging of Prostate Cells"],"prefix":"10.1002","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9460-4328","authenticated-orcid":false,"given":"William L.","family":"Turnbull","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Western Ontario  1151\u2005Richmond Street London Ontario N6A 5B7 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0941-4731","authenticated-orcid":false,"given":"Leonard G.","family":"Luyt","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Western Ontario  1151\u2005Richmond Street London Ontario N6A 5B7 Canada"},{"name":"London Regional Cancer Program Lawson Health Research Institute  790\u2005Commissioners Road East London Ontario N6A 4\u2005L6 Canada"},{"name":"Departments of Oncology and Medical Imaging University of Western Ontario  1151\u2005Richmond Street London Ontario N6A 5B7 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,9,5]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12020-013-0032-x"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1097\/MCO.0b013e32833106ee"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrurol.2013.43"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/pros.10128"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1097-0045(19990801)40:3<200::AID-PROS8>3.0.CO;2-3"},{"key":"e_1_2_7_6_1","first-page":"287","volume":"8","author":"Kriedt C. 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