{"id":6724,"date":"2017-10-28T12:56:32","date_gmt":"2017-10-28T12:56:32","guid":{"rendered":"https:\/\/www.vef.unizg.hr\/news\/new-quinoline-arylamidine-hybrids-synthesis-dna-rna-binding-and-antitumor-activity\/"},"modified":"2017-10-28T12:56:32","modified_gmt":"2017-10-28T12:56:32","slug":"new-quinoline-arylamidine-hybrids-synthesis-dna-rna-binding-and-antitumor-activity","status":"publish","type":"post","link":"https:\/\/www.vef.unizg.hr\/en\/research-cat\/new-quinoline-arylamidine-hybrids-synthesis-dna-rna-binding-and-antitumor-activity\/","title":{"rendered":"Krstulovi\u0107 i sur. (2017): New Quinoline-Arylamidine Hybrids : Synthesis, DNA\/RNA Binding and Antitumor Activity.European Journal of Medicinal Chemistry."},"content":{"rendered":"<h4><a href=\"https:\/\/doi.org\/10.1016\/j.ejmech.2017.05.054\">https:\/\/doi.org\/10.1016\/j.ejmech.2017.05.054<\/a><\/h4>\n<h3 class=\"section-title\" style=\"text-align: left;\">Abstract<\/h3>\n<div id=\"abssec0010\">\n<p id=\"abspara0010\">Four series of new hybrid molecules with 7-chloroquinoline and arylamidine moieties joined through the rigid &#8211;<em>O<\/em>&#8211; (groups\u00a0<strong>I (2a-g)<\/strong>\u00a0and\u00a0<strong>II<\/strong>\u00a0(<strong>5a-g)<\/strong>) or flexible -NH-CH<sub>2<\/sub>-CH<sub>2<\/sub>&#8211;<em>O<\/em>&#8211; (groups\u00a0<strong>III (8a-g)<\/strong>\u00a0and\u00a0<strong>IV (10a-g)<\/strong>) linker were synthesized, and their DNA\/RNA binding properties and\u00a0<a title=\"Learn more about Cytotoxicity\" href=\"https:\/\/www.sciencedirect.com\/topics\/pharmacology-toxicology-and-pharmaceutical-science\/cytotoxicity\">cytotoxic<\/a>\u00a0activity were tested, against several human cancer lines. The compounds and their interaction with\u00a0<a title=\"Learn more about Nucleic acid\" href=\"https:\/\/www.sciencedirect.com\/topics\/biochemistry-genetics-and-molecular-biology\/nucleic-acid\">DNA and RNA<\/a>\u00a0were studied by\u00a0<a title=\"Learn more about UV\/VIS Spectroscopy\" href=\"https:\/\/www.sciencedirect.com\/topics\/chemistry\/uv-vis-spectroscopy\">UV\u2013Vis<\/a>\u00a0and CD spectroscopy. The obtained results showed that the\u00a0<a title=\"Learn more about Ligand (biochemistry)\" href=\"https:\/\/www.sciencedirect.com\/topics\/pharmacology-toxicology-and-pharmaceutical-science\/ligand-biochemistry\">binding affinity<\/a>\u00a0of the investigated compounds increases proportionally with the increase of the length and number of groups able to form\u00a0<a title=\"Learn more about Hydrogen bond\" href=\"https:\/\/www.sciencedirect.com\/topics\/pharmacology-toxicology-and-pharmaceutical-science\/hydrogen-bond\">hydrogen bonds<\/a>\u00a0with ds-polynucleotides. Improvement of binding was additionally achieved by reduction of the structural rigidity of the investigated compounds, new hybrid compounds preferentially bind to ctDNA. For most of them the DNA\/RNA grooves are dominant\u00a0<a title=\"Learn more about Binding sites\" href=\"https:\/\/www.sciencedirect.com\/topics\/chemistry\/binding-sites\">binding sites<\/a>, except for the compounds from group\u00a0<strong>II<\/strong>\u00a0for which intercalation in polyA-polyU was the dominant binding mode. The\u00a0<a title=\"Learn more about antiproliferative\" href=\"https:\/\/www.sciencedirect.com\/topics\/chemistry\/antiproliferative\">antiproliferative effects<\/a>\u00a0were tested by the MTT test on normal (MDCK1), carcinoma (HeLa and CaCo2) and leukemia cell lines (Raji and K462). The GI<sub>50<\/sub>\u00a0values for all investigated compounds ranged from 5 to more than 100\u00a0\u00d7\u00a010<sup>\u22126<\/sup>\u00a0mol\u00a0dm<sup>\u22123<\/sup>. Carcinoma cells were more resistant to the investigated compounds than leukemia cells. The most effective compounds against leukemia cell lines were from group\u00a0<strong>IV (10a-g)<\/strong>, with GI<sub>50<\/sub>\u00a0values ranging from of 5 and 35\u00a0\u00d7\u00a010<sup>\u22126<\/sup>\u00a0mol\u00a0dm<sup>\u22123<\/sup>. The\u00a0<a title=\"Learn more about Cell cycle\" href=\"https:\/\/www.sciencedirect.com\/topics\/biochemistry-genetics-and-molecular-biology\/cell-cycle\">cell cycle<\/a>\u00a0arrest was investigated by flow\u00a0<a title=\"Learn more about cytometry\" href=\"https:\/\/www.sciencedirect.com\/topics\/chemistry\/cytometry\">cytometry<\/a>\u00a0and the obtained results indicate that the selected compounds,\u00a0<strong>2d<\/strong>,\u00a0<strong>2e<\/strong>,\u00a0<strong>8a<\/strong>,\u00a0<strong>10d<\/strong>,\u00a0<strong>10e<\/strong>, and\u00a0<strong>10f,<\/strong>\u00a0induce changes in the cell cycle of treated cells, but the cycle phase distribution varies between them. A significant decrease in the number of cells in\u00a0<a title=\"Learn more about S phase\" href=\"https:\/\/www.sciencedirect.com\/topics\/biochemistry-genetics-and-molecular-biology\/s-phase\">S phase<\/a>\u00a0(p\u00a0&lt;\u00a00.001) was observed in all treated cells, but only\u00a0<strong>10d<\/strong>\u00a0and\u00a0<strong>10f<\/strong>\u00a0induce cell cycle arrest at G0\/G1 phase, dominantly.<\/p>\n<\/div>\n<p><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0223523417304233\">https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0223523417304233<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>https:\/\/doi.org\/10.1016\/j.ejmech.2017.05.054 Abstract Four series of new hybrid molecules with 7-chloroquinoline and arylamidine moieties joined through the rigid &#8211;O&#8211; (groups\u00a0I (2a-g)\u00a0and\u00a0II\u00a0(5a-g)) or flexible -NH-CH2-CH2&#8211;O&#8211; (groups\u00a0III (8a-g)\u00a0and\u00a0IV (10a-g)) linker were synthesized, and their DNA\/RNA binding properties and\u00a0cytotoxic\u00a0activity were tested, against several human cancer lines. The compounds and their interaction with\u00a0DNA and RNA\u00a0were studied by\u00a0UV\u2013Vis\u00a0and CD spectroscopy. The&#8230;<\/p>\n","protected":false},"author":2,"featured_media":6086,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[326,327],"tags":[],"class_list":["post-6724","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-research-cat","category-scientific-highlights"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.4 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Krstulovi\u0107 i sur. (2017): New Quinoline-Arylamidine Hybrids : Synthesis, DNA\/RNA Binding and Antitumor Activity.European Journal of Medicinal Chemistry. - Veterinarski fakultet<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.vef.unizg.hr\/en\/research-cat\/new-quinoline-arylamidine-hybrids-synthesis-dna-rna-binding-and-antitumor-activity\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Krstulovi\u0107 i sur. 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