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Their association with the nucleic acids was investigated by spectrometric titrations, CD and LD spectroscopy, and with DNA\u2010melting analysis. Both ligands bind to duplex DNA by intercalation and to G4\u2010DNA by terminal \u03c0 stacking. At neutral conditions, they bind with higher affinity (<jats:italic>K<\/jats:italic><jats:sub>b<\/jats:sub>=10<jats:sup>5<\/jats:sup>\u221210<jats:sup>6<\/jats:sup>\u2005M<jats:sup>\u22121<\/jats:sup>) to representative quadruplex forming oligonucleotides <jats:bold>22AG<\/jats:bold>, <jats:bold>c\u2010myc<\/jats:bold>, <jats:bold>c\u2010kit<\/jats:bold>, and <jats:bold>a2<\/jats:bold>, than to duplex calf thymus (ct) DNA (<jats:italic>K<\/jats:italic><jats:sub>b<\/jats:sub>=5\u20107\u00d710<jats:sup>4<\/jats:sup>\u2005M<jats:sup>\u22121<\/jats:sup>). At pH\u20055, however, the affinity of <jats:bold>3\u2009a<\/jats:bold> towards G4\u2010DNA <jats:bold>22AG<\/jats:bold> is higher (<jats:italic>K<\/jats:italic><jats:sub>b<\/jats:sub>=1.2\u00d710<jats:sup>6<\/jats:sup>\u2005M<jats:sup>\u22121<\/jats:sup>), whereas the binding constant towards ct DNA is lower (<jats:italic>K<\/jats:italic><jats:sub>b<\/jats:sub>=3.9\u00d710<jats:sup>3<\/jats:sup>\u2005M<jats:sup>\u22121<\/jats:sup>) than under neutral conditions. Notably, the association of the ligand with DNA results in characteristic changes of the absorption and emission properties under specific conditions, which may be used for optical DNA detection. Other than the parent berberine, the ligands do not show a noticeable increase of their very low intrinsic emission intensity upon association with DNA at neutral conditions. In contrast, a fluorescence light\u2010up effect was observed upon association to duplex (<jats:italic>\u03a6<\/jats:italic><jats:sub>fl<\/jats:sub>=0.01) and quadruplex DNA (<jats:italic>\u03a6<\/jats:italic><jats:sub>fl<\/jats:sub>=0.04) at pH\u20055. This fluorimetric response to G4\u2010DNA association in combination with the distinct, red\u2010shifted absorption under these conditions provides a simple and conclusive optical detection of G4\u2010DNA at lower pH.<\/jats:p>","DOI":"10.1002\/chem.202100297","type":"journal-article","created":{"date-parts":[[2021,4,15]],"date-time":"2021-04-15T14:59:42Z","timestamp":1618498782000},"page":"8580-8589","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Selective, pH\u2010Dependent Colorimetric and Fluorimetric Detection of Quadruplex DNA with 4\u2010Dimethylamino(phenyl)\u2010Substituted Berberine Derivatives"],"prefix":"10.1002","volume":"27","author":[{"given":"Peter Jonas","family":"Wickhorst","sequence":"first","affiliation":[{"name":"Department of Chemistry \u2013 Biology University of Siegen, and Center of Micro- and Nanochemistry and Engineering (<i>C\u03bc<\/i>)  Adolf-Reichwein-Str. 2 57068 Siegen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0969-0426","authenticated-orcid":false,"given":"Heiko","family":"Ihmels","sequence":"additional","affiliation":[{"name":"Department of Chemistry \u2013 Biology University of Siegen, and Center of Micro- and Nanochemistry and Engineering (<i>C\u03bc<\/i>)  Adolf-Reichwein-Str. 2 57068 Siegen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,5,5]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201800430"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b10850"},{"key":"e_1_2_8_4_1","unstructured":"\u00a0"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC09771F"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbrc.2020.02.114"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00774D"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00216-010-4304-5"},{"key":"e_1_2_8_9_1","unstructured":"\u00a0"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.3389\/fchem.2020.00112"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/jbio.202000158"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b11134"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC08107G"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900263j"},{"key":"e_1_2_8_15_1","unstructured":"\u00a0"},{"key":"e_1_2_8_16_2","doi-asserted-by":"crossref","unstructured":"H.\u2005K. 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