title: Design, regioselective synthesis and cytotoxic evaluation of 2-aminoimidazole-quinoline hybrids against cancer and primary endothelial cells.
abstract: In search of new selective anti-cancer agents, a series of sixteen novel 2-aminoimidazole-quinoline hybrid compounds (5a-5p) have been designed and synthesized regioselectively. We have characterized the compounds extensively using IR, 1D and 2D NMR Spectroscopy and mass spectrometry. The cytotoxicity studies against different cancer cell lines showed that the compound 5a (Imd-Ph) emerged as a potent cytotoxic scaffold. Imd-Ph (5a) exhibited a selective anticancer activity against human colon cancer cell line (HCT-116, DLD-1) and was found relatively non-toxic to breast cancer cells (MDA-MB-231) as well as to normal primary endothelial cells (HUVEC). Structure-activity relationship of imidazole-quinoline hybrid scaffolds revealed differential and selective toxicities exerted by the different derivatives against cancer and normal cells. Structural modification of the scaffold with library of a wide variety of substituents may lead to the development of novel selective anti-cancer agents in the future.
authors.affiliation: Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar 125001, Haryana, India; Department of Chemistry, M.M. University, Mullana, Ambala 133207, Haryana, India.
authors.forename: Kuldeep
authors.initials: K
authors.lastname: Singh
authors.affiliation: Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar 125001, Haryana, India.
authors.forename: Vikas
authors.initials: V
authors.lastname: Verma
authors.affiliation: Laboratory of Nanotechnology and Chemical Biology, Regional Centre for Biotechnology, Gurgaon 122016, Haryana, India.
authors.forename: Kavita
authors.initials: K
authors.lastname: Yadav
authors.affiliation: Laboratory of Nanotechnology and Chemical Biology, Regional Centre for Biotechnology, Gurgaon 122016, Haryana, India.
authors.forename: Vedagopuram
authors.initials: V
authors.lastname: Sreekanth
authors.affiliation: Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar 125001, Haryana, India. Electronic address: dk_ic@yahoo.com.
authors.forename: Devinder
authors.initials: D
authors.lastname: Kumar
authors.affiliation: Laboratory of Nanotechnology and Chemical Biology, Regional Centre for Biotechnology, Gurgaon 122016, Haryana, India.
authors.forename: Avinash
authors.initials: A
authors.lastname: Bajaj
authors.affiliation: Department of Chemistry, M.M. University, Mullana, Ambala 133207, Haryana, India.
authors.forename: Vinod
authors.initials: V
authors.lastname: Kumar
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000188:drug therapy* / Q000473:pathology; D049109:Cell Proliferation / Q000187:drug effects; D002478:Cells, Cultured; D003110:Colonic Neoplasms / Q000188:drug therapy* / Q000473:pathology; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D005260:Female; D061307:Human Umbilical Vein Endothelial Cells / Q000187:drug effects*; D006801:Humans; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D007093:Imidazoles; D011804:Quinolines; C014973:2-aminoimidazole; C037219:quinoline
keywords: 2-Aminoimidazole; Cytotoxicity; Quinoline; Regioselectivity; Selective anticancer agents