Gold(III) compounds of 1,4,7-triazacyclononane showing high cytotoxicity against A-549 and HCT-116 tumor cell lines

Shi, Pengfei; Jiang, Qin; Lin, Jun; Zhao, Yongmei; Lin, Liping; Guo, Zijian

doi:10.1016/j.jinorgbio.2005.12.020

Cited by 32 publications

(15 citation statements)

References 40 publications

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“…The cation (25) is an example of a macrocyclic compound containing amine donor atoms. This is more active than cisplatin (1) against lung carcinoma (A-549) and hypoxia-conditioned colon (HCT-116) cancer cells (Shi et al, 2006a). This compound can apparently also induce distortion of the DNA double helix, indicating a possible mechanism of action.…”

Section: Gold(iii) Compoundsmentioning

confidence: 92%

Anti-cancer potential of gold complexes

2008

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A full range of gold compounds is currently being investigated for their potential as anti-tumor agents. Gold(I) compounds related to the anti-arthritic drug continue to attract attention, especially those carrying biologically active molecules with anti-tumor activity in their own right. Tetrahedrally coordinated gold(I) compounds, that possibly target mitochondria, are under development with a particular focus upon moderating their hydrophilicity. A resurgence of interest in square-planar gold(III) compounds has occurred in the last decade. A wide variety of species: mono- and di-nuclear, neutral and charged, coordination and organometallic, etc. are being developed. Supporting many investigations are studies of mechanistic aspects of gold compounds but a clear understanding of the mechanism of action of these compounds has yet to be delineated.

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Section: Gold(iii) Compoundsmentioning

confidence: 92%

Anti-cancer potential of gold complexes

2008

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“…22–24 (Chart 1a) or macrocyclic ligands25,26 or dithiocarbamato ligands with S-donor atoms (Chart 1d)27–29); b) organometallic complexes with an N-C30 (e.g. DAMP = o -C 6 H 4 CH 2 NMe 2, Chart 1b)31–36 or CNC-pincer backbone37 or c) gold(III) complexes containing bioligands (e.g.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Apoptosis-Inducing Iminophosphorane Organogold(III) Complexes and Study of Their Interactions with Biomolecular Targets

et al. 2009

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New stable cationic organogold(III) complexes containing the 'pincer' iminophosphorane ligand (2-C 6 H 4 -PPh 2 =NPh) have been prepared by reaction of the previously described [Au{κ 2 -C,N-C 6 H 4 (PPh 2 =N(C 6 H 5 )-2}Cl 2 ] 1 and a combination of sodium or silver salts and appropriate ligands. The presence of the P atom in the PR 3 fragment has been used as a "spectroscopic marker" to study the in vitro stability (and oxidation state) of the new organogold complexes in solvents like DMSO and water. Compounds with dithiocarbamato ligands and water-soluble phosphines of the general type [Au{κ 2 -C,NC 6 H 4 (PPh 2 =N(C 6 H 5 )-2}(S 2 CN-R 2 )]PF 6 (R = Me 2; Bz 3) and [Au{κ 2 -C,N-C 6 H 4 (PPh 2 =N(C 6 H 5 )-2}(PR 3 ) n Cl]PF 6 (PR 3 = P{Cp(m-C 6 H 4 -SO 3 Na) 2 } n = 1 4, n = 2 TPA {1,3,5-triaza-7-phosphaadamantane} 5) have been synthesized and characterized in solution and in the solid state (the crystal structure of 2 has been determined by X-ray diffraction studies). Complexes 1-5 have been tested as potential anticancer agents and their cytotoxicity properties were evaluated in vitro against HeLa human cervical carcinoma and Jurkat-T acute lymphoblastic leukemia cells. Compounds 2 and 3 are quite cytotoxic for these two cell lines. There is a preferential induction of apoptosis in HeLa cells after treatment with 1-5. However in the case of the more cytotoxic complex (2), cell death is activated due to both apoptosis and necrosis. The interactions of 1-5 with Calf Thymus DNA have been evaluated by Thermal Denaturation methods. All these complexes show no or little (electrostatic) interaction with DNA. The interaction of 2 with two model proteins (cytochrome c and thioredoxin reductase) has been analyzed by spectroscopic methods (vis-UV and fluorescence). Compound 2 manifests a high reactivity toward both proteins. The mechanistic implications of these results are discussed here.

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“…The cyclic voltammetry of the complex recorded in aqueous solution indicates a reversible one-electron redox reaction. The activity of dismutation of superoxide ð Å O À 2 Þ of the complex in the riboflavin-methionine-nitro blue tetrazolium assay has been researched.Ó 2008 Elsevier B.V. All rights reserved.The macrocyclic ligand, 1,4,7-triazacyclononane (tacn), has been well-studied and numerous metal complexes of this and related N-functionalised derivatives have been synthesized [1][2][3][4][5][6][7][8][9]. Due to their large number of nitrogens, these kinds of ligands are able to form very interesting and stable complexes.…”

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confidence: 99%