{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,10]],"date-time":"2026-10-10T04:37:01Z","timestamp":1791607021272,"version":"4.3.4"},"reference-count":107,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2024,5,13]],"date-time":"2024-05-13T00:00:00Z","timestamp":1715558400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004442","name":"National Science Center","doi-asserted-by":"publisher","award":["2021\/05\/X\/ST4\/01006"],"award-info":[{"award-number":["2021\/05\/X\/ST4\/01006"]}],"id":[{"id":"10.13039\/501100004442","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004442","name":"National Science Center","doi-asserted-by":"publisher","award":["FdS2017Garribba"],"award-info":[{"award-number":["FdS2017Garribba"]}],"id":[{"id":"10.13039\/501100004442","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004442","name":"National Science Center","doi-asserted-by":"publisher","award":["FJC2019-039135-I"],"award-info":[{"award-number":["FJC2019-039135-I"]}],"id":[{"id":"10.13039\/501100004442","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100014810","name":"Fondazione di Sardegna","doi-asserted-by":"publisher","award":["2021\/05\/X\/ST4\/01006"],"award-info":[{"award-number":["2021\/05\/X\/ST4\/01006"]}],"id":[{"id":"10.13039\/100014810","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100014810","name":"Fondazione di Sardegna","doi-asserted-by":"publisher","award":["FdS2017Garribba"],"award-info":[{"award-number":["FdS2017Garribba"]}],"id":[{"id":"10.13039\/100014810","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100014810","name":"Fondazione di Sardegna","doi-asserted-by":"publisher","award":["FJC2019-039135-I"],"award-info":[{"award-number":["FJC2019-039135-I"]}],"id":[{"id":"10.13039\/100014810","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Spanish MICINN Juan de la Cierva program","award":["2021\/05\/X\/ST4\/01006"],"award-info":[{"award-number":["2021\/05\/X\/ST4\/01006"]}]},{"name":"Spanish MICINN Juan de la Cierva program","award":["FdS2017Garribba"],"award-info":[{"award-number":["FdS2017Garribba"]}]},{"name":"Spanish MICINN Juan de la Cierva program","award":["FJC2019-039135-I"],"award-info":[{"award-number":["FJC2019-039135-I"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The interactions with calf thymus DNA (CT-DNA) of three Schiff bases formed by the condensation of hesperetin with benzohydrazide (HHSB or L1H3), isoniazid (HIN or L2H3), or thiosemicarbazide (HTSC or L3H3) and their CuII complexes (CuHHSB, CuHIN, and CuHTSC with the general formula [CuLnH2(AcO)]) were evaluated in aqueous solution both experimentally and theoretically. UV\u2013Vis studies indicate that the ligands and complexes exhibit hypochromism, which suggests helical ordering in the DNA helix. The intrinsic binding constants (Kb) of the Cu compounds with CT-DNA, in the range (2.3\u20139.2) \u00d7 106, from CuHTSC to CuHHSB, were higher than other copper-based potential drugs, suggesting that \u03c0\u2013\u03c0 stacking interaction due to the presence of the aromatic rings favors the binding. Thiazole orange (TO) assays confirmed that ligands and Cu complexes displace TO from the DNA binding site, quenching the fluorescence emission. DFT calculations allow for an assessment of the equilibrium between [Cu(LnH2)(AcO)] and [Cu(LnH2)(H2O)]+, the tautomer that binds CuII, amido (am) and not imido (im), and the coordination mode of HTSC (O\u2212, N, S), instead of (O\u2212, N, NH2). The docking studies indicate that the intercalative is preferred over the minor groove binding to CT-DNA with the order [Cu(L1H2am)(AcO)] &gt; [Cu(L2H2am)(AcO)] \u2248 TO \u2248 L1H3 &gt; [Cu(L3H2am)(AcO)], in line with the experimental Kb constants, obtained from the UV\u2013Vis spectroscopy. Moreover, dockings predict that the binding strength of [Cu(L1H2am)(AcO)] is larger than [Cu(L1H2am)(H2O)]+. Overall, the results suggest that when different enantiomers, tautomers, and donor sets are possible for a metal complex, a computational approach should be recommended to predict the type and strength of binding to DNA and, in general, to macromolecules.<\/jats:p>","DOI":"10.3390\/ijms25105283","type":"journal-article","created":{"date-parts":[[2024,5,14]],"date-time":"2024-05-14T08:03:08Z","timestamp":1715673788000},"page":"5283","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Experimental and Computational Studies on the Interaction of DNA with Hesperetin Schiff Base CuII Complexes"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8027-3161","authenticated-orcid":false,"given":"Federico","family":"Pisanu","sequence":"first","affiliation":[{"name":"Dipartimento di Medicina, Chirurgia e Farmacia, Universit\u00e0 di Sassari, Viale San Pietro, I-07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1989-5989","authenticated-orcid":false,"given":"Anna","family":"Sykula","sequence":"additional","affiliation":[{"name":"Faculty of Biotechnology and Food Sciences, Institute of Natural Products and Cosmetics, Lodz University of Technology, Stefanowskiego 2\/22, 90-537 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9657-1788","authenticated-orcid":false,"given":"Giuseppe","family":"Sciortino","sequence":"additional","affiliation":[{"name":"Department de Qu\u00edmica, Universitat Aut\u00f2noma de Barcelona, Cerdanyola del Vall\u00e9s, 08193 Barcelona, Spain"},{"name":"Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology (BIST), 43007 Tarragona, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Feliu","family":"Maseras","sequence":"additional","affiliation":[{"name":"Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology (BIST), 43007 Tarragona, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elzbieta","family":"Lodyga-Chruscinska","sequence":"additional","affiliation":[{"name":"Faculty of Biotechnology and Food Sciences, Institute of Natural Products and Cosmetics, Lodz University of Technology, Stefanowskiego 2\/22, 90-537 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7229-5966","authenticated-orcid":false,"given":"Eugenio","family":"Garribba","sequence":"additional","affiliation":[{"name":"Dipartimento di Medicina, Chirurgia e Farmacia, Universit\u00e0 di Sassari, Viale San Pietro, I-07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,5,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1515\/revic-2021-0034","article-title":"Schiff bases and their metal complexes with biologically compatible metal ions; biological importance, recent trends and future hopes","volume":"42","author":"Khan","year":"2022","journal-title":"Rev. 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