{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,11]],"date-time":"2026-04-11T12:01:44Z","timestamp":1775908904665,"version":"3.50.1"},"reference-count":55,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2025,11,3]],"date-time":"2025-11-03T00:00:00Z","timestamp":1762128000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2025,11,3]],"date-time":"2025-11-03T00:00:00Z","timestamp":1762128000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100004488","name":"Croatian Science Foundation","doi-asserted-by":"publisher","award":["IP\u20102024\u201005\u22127208"],"award-info":[{"award-number":["IP\u20102024\u201005\u22127208"]}],"id":[{"id":"10.13039\/501100004488","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemMedChem"],"published-print":{"date-parts":[[2025,12,15]]},"abstract":"<jats:p>\n                    A series of cyano\u2010 and amidino\u2010substituted derivatives of\n                    <jats:italic>N<\/jats:italic>\n                    3\u2010methyl\u2010imidazo[4,5\u2010\n                    <jats:italic>b<\/jats:italic>\n                    ]pyridines is designed and synthesized to investigate their biological activity. The previously published synthetic methods for the synthesis of targeted derivatives are further optimized to obtain higher yields. In order to investigate how the number, the position, and the type of amidine groups affect biological activity, targeted compounds are substituted with amidine groups on opposite sides of molecules. All compounds demonstrated moderate to strong antiproliferative activity in vitro against tested cancer cell lines with good selectivity against HeLa cancer cell lines. 6\u2010Benzonitril\u2010substituted compound\n                    <jats:bold>12<\/jats:bold>\n                    showed pronounced antiproliferative activity against HeLa (IC\n                    <jats:sub>50<\/jats:sub>\n                    0.7 \u00b5M) and MCF7 (IC\n                    <jats:sub>50<\/jats:sub>\n                    0.6 \u00b5M) cancer cell lines. Compound\n                    <jats:bold>19<\/jats:bold>\n                    bearing two imidazolinyl amidine groups also showed selective activity against MCF7 (IC\n                    <jats:sub>50<\/jats:sub>\n                    0.6 \u00b5M) cancer cell line. Spectroscopic investigation of the interaction of the most active derivatives with calf thymus\n                    <jats:italic>\u2010<\/jats:italic>\n                    DNA is monitored by UV\/Vis, emission, and circular dichroism spectroscopy. The lead compound\n                    <jats:bold>19<\/jats:bold>\n                    is shown to bind in the minor groove of DNA, suggesting a possible mechanism of action in tumor cells. The compounds are also tested for their antibacterial activity in vitro, but they showed no antibacterial activity against the tested bacterial strains.\n                  <\/jats:p>","DOI":"10.1002\/cmdc.202500640","type":"journal-article","created":{"date-parts":[[2025,11,3]],"date-time":"2025-11-03T23:40:57Z","timestamp":1762213257000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Synthesis, Biological Evaluation, and Interaction with Calf Thymus\u2010DNA of Mono\u2010 and Diamidino\u2010Substituted Imidazo[4,5\u2010\n                    <i>b<\/i>\n                    ]pyridines"],"prefix":"10.1002","volume":"20","author":[{"given":"Ida Bo\u010dek","family":"Pavlinac","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry University of Zagreb Faculty of Chemical Engineering and Technology  Maruli\u0107ev trg 19 10000 Zagreb Croatia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Corina","family":"\u0160ljubura","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry University of Zagreb Faculty of Chemical Engineering and Technology  Maruli\u0107ev trg 19 10000 Zagreb Croatia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Katarina","family":"Zlati\u0107","sequence":"additional","affiliation":[{"name":"Division of Molecular Medicine Institute Ru\u0111er Bo\u0161kovi\u0107  Bijeni\u010dka cesta 54 10000 Zagreb Croatia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marijeta","family":"Kralj","sequence":"additional","affiliation":[{"name":"Division of Molecular Medicine Institute Ru\u0111er Bo\u0161kovi\u0107  Bijeni\u010dka cesta 54 10000 Zagreb Croatia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ivana","family":"Fabijani\u0107","sequence":"additional","affiliation":[{"name":"Division of Organic Chemistry and Biochemistry Institute Ru\u0111er Bo\u0161kovi\u0107  Bijeni\u010dka cesta 54 10000 Zagreb Croatia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mihailo","family":"Banjanac","sequence":"additional","affiliation":[{"name":"Pharmacology In Vitro Selvita Ltd.  Prilaz Baruna Filipovi\u0107a 29 10000 Zagreb Croatia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marijana Radi\u0107","family":"Stojkovi\u0107","sequence":"additional","affiliation":[{"name":"Division of Organic Chemistry and Biochemistry Institute Ru\u0111er Bo\u0161kovi\u0107  Bijeni\u010dka cesta 54 10000 Zagreb Croatia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3994-0054","authenticated-orcid":false,"given":"Marijana","family":"Hranjec","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry University of Zagreb Faculty of Chemical Engineering and Technology  Maruli\u0107ev trg 19 10000 Zagreb Croatia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,11,3]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/med.21278"},{"key":"e_1_2_9_3_1","first-page":"103730","volume":"28","author":"Wu K.","year":"2023","journal-title":"Drug Discov."},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.04.023"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-40032-3"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbamcr.2019.118539"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CP05537H"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.biophys.29.1.439"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.14.93"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschembio.4c00800"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8MD00425K"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/tx00006a001"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2003.08.012"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.05.030"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/cb400431f"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar030287f"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1387-2656(00)05035-3"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0210998"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC02990G"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1093\/carcin\/10.8.1389"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkt955"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.2421408"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1038\/382559a0"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0959-440X(03)00081-2"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0968-0896(01)00262-0"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/9781788012928-00298"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1349-7006.2011.02098.x"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1222035110"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biochi.2008.02.017"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pntd.0001734"},{"key":"e_1_2_9_31_1","first-page":"876","volume":"11","author":"Paine M. 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