title: Synthesis and biological evaluation of cytotoxic activity of novel anthracene L-rhamnopyranosides.
abstract: A series of anthracene L-rhamnopyranosides were designed and synthesized in a practical way and their cytotoxic activity was examined in vitro. Most compounds exhibited both potent cytotoxicity against several tumor cell lines and high DNA binding capacity. The preliminary results showed that subtle modifications of rhamnosyl moiety in anthracene rhamnosides with acetyl group had a selective toxicity for different tumor cells and the displacement of C-10 carbonyl group in emodin by acetylmethylene group was helpful to improve the inhibitory activity. Lipophilicity of the anthracene glycosides was not a crucial factor for cytotoxicity and most molecules with good cytotoxicity could inhibit the catalytic activity of Top2alpha.
authors.affiliation: College of Resources and Environment, South China Agricultural University, Guangzhou 510642, China.
authors.forename: Gaopeng
authors.initials: G
authors.lastname: Song
authors.forename: Hongchun
authors.initials: H
authors.lastname: Liu
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.forename: Meiyu
authors.initials: M
authors.lastname: Geng
authors.forename: Yingxia
authors.initials: Y
authors.lastname: Li
mesh_terms: D000873:Anthracenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D003603:Cytotoxins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004247:DNA / Q000378:metabolism; D004250:DNA Topoisomerases, Type II / Q000378:metabolism; D006801:Humans; D009005:Monosaccharides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009369:Neoplasms / Q000188:drug therapy*; D059005:Topoisomerase II Inhibitors
chemical_list: D000873:Anthracenes; D003603:Cytotoxins; D009005:Monosaccharides; D059005:Topoisomerase II Inhibitors; D004247:DNA; D004250:DNA Topoisomerases, Type II; C034020:anthracene