title: Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin.
abstract: The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity.
authors.affiliation: School of Chinese Medicine, Hong Kong Baptist University, Kowloon Tong, Kowloon, Hong Kong.
authors.forename: Hao
authors.initials: H
authors.lastname: He
authors.forename: Li-Ping
authors.initials: LP
authors.lastname: Bai
authors.forename: Zhi-Hong
authors.initials: ZH
authors.lastname: Jiang
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D054856:G-Quadruplexes; D006031:Glycosylation; D006801:Humans; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000617:Aminoglycosides; D009285:Naphthoquinones; C018204:alkannin; C016101:shikonin; D004247:DNA