title: Novel imidazo[4,5-b]pyridine and triaza-benzo[c]fluorene derivatives: synthesis, antiproliferative activity and DNA binding studies.
abstract: In the present paper, we have described the synthesis and biological activity of the novel derivatives of imidazo[4,5-b]pyridines and triaza-benzo[c]fluorenes (7-21, 24-26, 28-29). A preponderance of these compounds exerted strong cytostatic effects on the panel of seven human tumour cell lines in a dose-dependent manner. In particular, imidazo[4,5-b]pyridines and triaza-benzo[c]fluorenes including 2-imidazolinyl derivatives showed the most potent antitumour activity. Similarly, triaza-benzo[c]fluorenes 18 and 20 induced strong growth inhibition of tested tumour cell lines, and showed low cytotoxicity in normal human fibroblasts. DNA interaction studies of these compounds demonstrated that N-methylated 16 and 2-imidazolinyl 28 triaza-benzo[c]fluorenes bind to DNA in an intercalative mode.
authors.affiliation: Faculty of Chemical Engineering and Technology, Department of Organic Chemistry, University of Zagreb, Marulićev trg 20, P. O. Box 177, HR-10000 Zagreb, Croatia. mhranjec@fkit.hr
authors.forename: Marijana
authors.initials: M
authors.lastname: Hranjec
authors.forename: Borka
authors.initials: B
authors.lastname: Lučić
authors.forename: Ivana
authors.initials: I
authors.lastname: Ratkaj
authors.forename: Sandra Kraljević
authors.initials: SK
authors.lastname: Pavelić
authors.forename: Ivo
authors.initials: I
authors.lastname: Piantanida
authors.forename: Krešimir
authors.initials: K
authors.lastname: Pavelić
authors.forename: Grace
authors.initials: G
authors.lastname: Karminski-Zamola
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D002417:Cattle; D002453:Cell Cycle / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004247:DNA / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects; D005449:Fluorenes / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D048288:Imidazolines / Q000138:chemical synthesis* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007364:Intercalating Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007700:Kinetics; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D005449:Fluorenes; D048288:Imidazolines; D007364:Intercalating Agents; D011725:Pyridines; D004247:DNA