title: Cytotoxicity of the traditional chinese medicine (TCM) plumbagin in its copper chemistry.
abstract: The anticancer traditional Chinese medicine (TCM), plumbagin (PLN), was isolated from Plumbago Zeylanica. Reaction of plumbagin with Cu(II) salt, afforded [Cu(PLN)(2)].2H(2)O (1). With 2,2'-bipyridine (bipy) as a co-ligand, PLN reacts with Cu(II) to give [Cu(PLN)(bipy)(H(2)O)](2)(NO(3))(2).4H(2)O (2). 1 and 2 were characterized by elemental analysis, IR, ESI-MS spectra. Their crystal structures were determined by single crystal X-ray diffraction methods. The in vitro cytotoxicity of PLN, 1 and 2 against seven human tumour cell lines was assayed. The metal-based compounds exhibit enhanced cytotoxicity vs. that of free PLN, suggesting that these compounds display synergy in the combination of metal ions with PLN. The binding properties of PLN, 1 and 2 to DNA were investigated through UV-vis, fluorescence, CD spectra, and gel mobility shift assay, which indicated that 1 and 2 were non-covalent binding and mainly intercalated the neighboring base pairs of DNA. PLN, 1 and 2 exhibit inhibition activity to topoisomerase I (TOPO I), but 1 and 2 were more effective than PLN.
authors.affiliation: Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education), School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin, 541004, P. R. China. chenzfubc@yahoo.com
authors.forename: Zhen-Feng
authors.initials: ZF
authors.lastname: Chen
authors.forename: Ming-Xiong
authors.initials: MX
authors.lastname: Tan
authors.forename: Li-Min
authors.initials: LM
authors.lastname: Liu
authors.forename: Yan-Cheng
authors.initials: YC
authors.lastname: Liu
authors.forename: Heng-Shan
authors.initials: HS
authors.lastname: Wang
authors.forename: Bin
authors.initials: B
authors.lastname: Yang
authors.forename: Yan
authors.initials: Y
authors.lastname: Peng
authors.forename: Hua-Gang
authors.initials: HG
authors.lastname: Liu
authors.forename: Hong
authors.initials: H
authors.lastname: Liang
authors.forename: Chris
authors.initials: C
authors.lastname: Orvig
mesh_terms: D015082:2,2'-Dipyridyl / Q000737:chemistry; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity*; D045744:Cell Line, Tumor; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity*; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry / Q000378:metabolism; D004264:DNA Topoisomerases, Type I / Q000378:metabolism; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008516:Medicine, Chinese Traditional; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D018517:Plant Roots / Q000737:chemistry; D029606:Plumbaginaceae / Q000737:chemistry; D059004:Topoisomerase I Inhibitors
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D056831:Coordination Complexes; D009285:Naphthoquinones; D059004:Topoisomerase I Inhibitors; D015082:2,2'-Dipyridyl; D003300:Copper; D004247:DNA; D004264:DNA Topoisomerases, Type I; C014758:plumbagin