Advances in copper complexes as anticancer agents.

Plumbagin is one of the simplest plant secondary metabolite of three major phylogenic families viz. Plumbaginaceae, Droseraceae, and Ebenceae, and exhibits highly potent biological activ- ities, including antioxidant, antiinflammatory, anticancer, antibacterial, and antifungal activities. Recent investigations indicate that these activities arise mainly out of its ability to undergo redox cycling, generating reactive oxygen species and chelating trace metals in biological system. The com- pound is endowed with a property to inhibit the drug efflux mechanism in drug-resistant bacteria, thereby allowing intracellular accumulation of the potent drug molecules. An interesting bioactivity exhibited by this compound is the elimination of stringent, conjugative, multidrug-resistant plasmids from several bacterial strains including opportunistic bacteria, such as Acinetobacter baumannii. Moreover, plumbagin effectively induces apoptosis and causes cell cycle arrest, which is, in part, due to the inactivation of NF-kB in cancer cells. Therefore, it has been suggested that designing ''hybrid drug molecules'' of plumbagin by combining it with other appropriate anticancer agents may lead to the generation of novel and potent anticancer drugs with pleiotropic action against human cancers. This comprehensive review is an attempt to understand the chemistry of plumbagin and catalog its biological

Perspectives on medicinal properties of plumbagin and its analogs

Organometallics, such as copper compounds, are cancer chemotherapeutics used alone or in combination with other drugs. One small group of copper complexes exerts an effective inhibitory action on topoisomerases, which participate in the regulation of DNA topology. Copper complexes inhibitors of topoisomerases 1 and 2 work by different molecular mechanisms, analyzed herein. They allow genesis of DNA breaks after the formation of a ternary complex, or act in a catalytic mode, often display DNA intercalative properties and ROS production, and sometimes display dual effects. These amplified actions have repercussions on the cell cycle checkpoints and death effectors. Copper complexes of topoisomerase inhibitors are analyzed in a broader synthetic view and in the context of cancer cell mutations. Finally, new emerging treatment aspects are depicted to encourage the expansion of this family of highly active anticancer drugs and to expend their use in clinical trials and future cancer therapy.

Copper Complexes as Anticancer Agents Targeting Topoisomerases I and II.

Lanthanide biochemistry-A surprise around every corner: lanthanides as biologically essential metals. This statement was until recently, unthinkable. This minireview presents the recent developments in the emerging field of rare-earth element biochemistry from a coordination chemist's point of view and discusses why nature might have chosen these elements to have a catalytic role in alcohol dehydrogenase enzymes as they are found in methanotrophic and methylotrophic bacteria.

Essential and Ubiquitous: The Emergence of Lanthanide Metallobiochemistry

Three water-soluble ruthenium(II) complexes with chiral 4-(2,3-dihydroxypropyl)-formamide oxoaporphine (FOA) were synthesized and characterized. It was found that these ruthenium(II) complexes exhibited considerable in vitro anticancer activities and that they were the effective stabilizers of telomeric and G-quadruplex-DNA (G4-DNA) in promoter of c-myc, which acted as a telomerase inhibitor targeting G4-DNA and induced cell senescence and apoptosis. Interestingly, the in vitro anticancer activity of 6 (LC-003) was higher than those of 4 (LC-001) and 5 (LC-002), more selective for BEL-7404 cells than for normal HL-7702 cells, and preferred to activate caspases-3/9. The different biological behaviors of the ruthenium complexes could be correlated with the chiral nature of 4-(2,3-dihydroxypropyl)-formamide oxoaporphine. More significantly, 6 exhibited effective inhibitory on tumor growth in BEL-7402 xenograft mouse model and higher in vivo safety than cisplatin. These mechanistic insights indicate that 6 di...

Water-Soluble Ruthenium(II) Complexes with Chiral 4-(2,3-Dihydroxypropyl)-formamide Oxoaporphine (FOA): In Vitro and in Vivo Anticancer Activity by Stabilization of G-Quadruplex DNA, Inhibition of Telomerase Activity, and Induction of Tumor Cell Apoptosis

Liriodenine (L), an active component of the anticancer traditional Chinese medicine (TCM), was isolated from Zanthoxylum nitidum. Its reactions with Pt(II) and Ru(II) afforded three metal complexes: cis-[PtCl2(L)] (1), cis-[PtCl2(L)(DMSO)] (2), and cis-[RuCl2(L)(DMSO)2]·1.5H2O (3), the crystal structures of L, 2 and 3 were determined by single-crystal X-ray diffraction methods. These complexes were fully characterized by elemental analysis, IR spectrophotometry, 1H and 13C NMR spectroscopies, and ES mass spectrometry. The in vitro cytotoxicity of L and complexes 1–3 against 11 human tumour cell lines was assayed. The metal-based compounds exhibit enhanced cytotoxicity vs. free L, suggesting that these compounds display synergy in the combination of metal ions and liriodenine. The binding properties of L and its complexes 1–3 to ct-DNA were investigated through UV-vis, fluorescence, CD spectra, viscosity and agarose gels electrophoretic measurements.

Potential new inorganic antitumour agents from combining the anticancer traditional Chinese medicine (TCM) liriodenine with metal ions, and DNA binding studies.

The anticancer traditional Chinese medicine (TCM), plumbagin (PLN), was isolated from Plumbago Zeylanica. Reaction of plumbagin with CuII salt, afforded [Cu(PLN)2]·2H2O (1). With 2,2′-bipyridine (bipy) as a co-ligand, PLN reacts with CuII to give [Cu(PLN)(bipy)(H2O)]2(NO3)2·4H2O (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.

Cytotoxicity of the traditional chinese medicine (TCM) plumbagin in its copper chemistry

Liriodenine (L), a natural alkaloid, was isolated as an active component from the anticancer traditional Chinese medicine (TCM), Zanthoxylum nitidum. It reacted with MnII, FeII, CoII and ZnII to afford four metal complexes: [MnCl2(L)2] (1), [FeCl2(L)2] (2), [Co(L)2(H2O)2·Co(L)2(CH3CH2OH)2](ClO4)4 (3), and [Zn2(L)2(μ2-Cl)2Cl2] (4), which were characterized by elemental analysis, IR, ESI-MS. Their crystal structures were determined by the single crystal X-ray diffraction method. The in vitro cytotoxicity of L and complexes 1–4 against 10 human tumour cell lines was assayed. Some of these metal-based compounds exhibited enhanced cytotoxicity vs. free L to selected tumour cell lines. The binding properties of L and its complexes 1–4 to ct-DNA were investigated by spectroscopic methods and viscosity measurements. Agarose gel electrophoresis experiments were also carried out to evaluate their unwinding ability towards plasmid DNA and their inhibition towards Topoisomerase I. All the results indicate that complexes 1–4 may bind more intensively to the DNA helix than does L, and intercalative binding for complexes 1–4 and electrostatic interactions for complexes 3–4 to DNA should be considered. For complex 4, covalent binding to DNA may exist. Of special note, all these metal complexes effectively inhibit Topoisomerase I even at low concentration (≤10 μM).

Divalent later transition metal complexes of the traditional chinese medicine (TCM) liriodenine: coordination chemistry, cytotoxicity and DNA binding studies

The invention discloses a metal chelate which takes plumbagin as ligand, and the synthesis method and application thereof. The metal chelate is represented by the right formula, wherein, M represents the metal ion able to accept lone pair electrons can be main group matel ion, or transition metal ion, or rare earth metal ion such as Ca(II), Mg(II), Sn(IV), Cu(II), Co(II), Ni(II), Zn(II), Fe(II), Mn(II), Ag(I), Mo(VI), Pd(II), Ru(III), W(VI), Pt(II), Y(III), La(III), Nd(III), Sm(III), Eu(III), Er(III). The invention synthesizes a series of metal chelate which takes plumbagin as ligand and reacts with the metal salt. The produced chelate has an inhibition to a plurality of tumor line. The result indicates a plurality of chelate having a more remarkable anti-tumor activity than the plumbaginand have a higher medicine value and can be used for the preparation of different anti-tumor medicine.

Metal complex using plumbagin as ligand, synthesizing method and usage thereof

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Potential new inorganic antitumour agents from combining the anticancer traditional Chinese medicine (TCM) liriodenine with metal ions, and DNA binding studies.

Cytotoxicity of the traditional chinese medicine (TCM) plumbagin in its copper chemistry

Divalent later transition metal complexes of the traditional chinese medicine (TCM) liriodenine: coordination chemistry, cytotoxicity and DNA binding studies

Metal complex using plumbagin as ligand, synthesizing method and usage thereof