title: Cytotoxicity and DNA binding property of phenanthrene imidazole with polyglycol side chains.
abstract: A series of phenanthrene imidazole with polyglycol side chain (2a-2c and 3a-3c) were synthesized and characterized by IR, NMR and MS. The cytotoxicity of 2a-2c and 3a-3c against cancer cell lines (HL-60, BGC-823, Bel-7402 and KB) in vitro were measured using MTT method. The DNA binding properties of 3a-3c were investigated by UV, fluorescence, CD spectroscopies and thermal denaturation. The results indicate that 2a exhibits higher cytotoxicity than cisplatin against BGC-823 and Bel-7402 cell lines, 3b and 3c exhibit higher cytotoxicity than 2b and 2c against BGC-823, Bel-7402 and KB cell lines. The cytotoxic effect of 2a-2c decrease with the increase of side chains length, the cytotoxic effect of 3a-3c increased with the increasing length of side chains against BGC-823, Bel-7402 and KB cell lines. Compounds 3a-3c intercalated DNA with a vertical orientation in the intercalation pocket. The binding constants of 3a-3c with Ct-DNA are 1.68×10(6), 1.51×10(6) and 0.709×10(6)M(-1), respectively. The binding affinity of 3a-3c with Ct-DNA trended to decrease with the increasing length of polyglycol side chains.
authors.affiliation: Chemical Biology Key Laboratory of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
authors.forename: Shuxiang
authors.initials: S
authors.lastname: Wang
authors.forename: Hongdong
authors.initials: H
authors.lastname: Li
authors.forename: Chao
authors.initials: C
authors.lastname: Chen
authors.forename: Jinchao
authors.initials: J
authors.lastname: Zhang
authors.forename: Shenghui
authors.initials: S
authors.lastname: Li
authors.forename: Xinying
authors.initials: X
authors.lastname: Qin
authors.forename: Xiaoliu
authors.initials: X
authors.lastname: Li
authors.forename: Kerang
authors.initials: K
authors.lastname: Wang
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004247:DNA / Q000378:metabolism*; D006018:Glycols / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D007093:Imidazoles / Q000737:chemistry* / Q000494:pharmacology*; D007364:Intercalating Agents / Q000737:chemistry / Q000494:pharmacology; D009369:Neoplasms / Q000188:drug therapy; D010616:Phenanthrenes / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D006018:Glycols; D007093:Imidazoles; D007364:Intercalating Agents; D010616:Phenanthrenes; C031181:phenanthrene; C029899:imidazole; D004247:DNA