Suppression of survival in human SKBR3 breast carcinoma in response to metal–chelator complexes is preferential for copper–dithiocarbamate

Viola-Rhenals, Maricela; Rieber, Manuel

doi:10.1016/j.bcp.2005.11.028

Cited by 25 publications

(28 citation statements)

References 40 publications

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“…Table 1. It is observed that both complexes show strong cytotoxic activities in vitro probably due to the complexes inducing DNA damage in cancer cells [14,15] and the features of the metal ions [42,43]. It is also observed that 2 shows more significant cytotoxic activities than 1 against the three human cancer cell lines, which is consistent with the results of DNA-binding studies.…”

Section: Viscosity Measurementssupporting

confidence: 88%

Synthesis and characterization of the Zn(II) and Cu(II) piperidinyl isoeuxanthone complexes: DNA-binding and cytotoxic activity

Wang

Shen

2009

European Journal of Medicinal Chemistry

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Section: Viscosity Measurementssupporting

confidence: 88%

Synthesis and characterization of the Zn(II) and Cu(II) piperidinyl isoeuxanthone complexes: DNA-binding and cytotoxic activity

Wang

Shen

2009

European Journal of Medicinal Chemistry

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“…The result of inhibitory effect in vitro is consistent with the result of DNA binding studies above, which may be due to the complexes inducing DNA damage in cancer cells 35) and the nature of the metal ions. 36,37) …”

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confidence: 99%

Antitumor Activity and DNA-Binding Investigations of the Zn(II) and Cu(II) Complexes with Isoeuxanthone

Wang

Shen

2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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Recently, more and more attention has been paid to xanthones that are widely present as a class of secondary metabolites in some higher plants and microorganisms. [1][2][3] These naturally occurring compounds and their synthetic analogs have been reported to exhibit multiple important pharmacological properties, such as anti-oxidant, anti-inflammatory, anti-malarial and anti-cancer activity, etc. [4][5][6][7][8][9] As shown in Fig. 1a, xanthones having three linear fused aromatic rings may be viewed as flavone derivatives in which the phenyl group is fused with the two aromatic rings. This structural 'similarity,' together with the aforementioned studies on hydroxyflavones and biological efficacy of xanthones enforced many scientists to isolate or synthesize appropriately modified derivatives for the development of prospective new drug candidates.10-12) Isoeuxanthone (Fig. 1b) is one of well-known xanthone derivatives which have diverse biological profiles.Since DNA is an important cellular receptor, many chemicals exert their antitumor effects to DNA thereby changing the replication of DNA and inhibiting the growth of the tumor cell, which is the basis of designing new and more efficient antitcancer drugs and their effectiveness depends on the mode and affinity of the binding.13) Similarly, interactions of metallic antitumor reagents with DNA are also very important in understanding the mechanisms of their antitumor activities.14,15) We were thus motivated to investigate metallic complexes of isoeuxanthone on their binding modes and affinities to DNA. Therefore, in this context, we report the synthesis and characterization of the mononuclear Zn(II) complex (1) and Cu(II) complex (2) with isoeuxanthone. The interactions of them with calf thymus (ct DNA) have also been studied by absorption spectroscopy, fluorescence spectroscopy, circular dichroism spectroscopy and viscosity measurements. In addition, they were evaluated for their cytotoxic activities toward human esophageal cancer (ECA109) and human gastric cancer (SGC7901) cells by microculture tetrazolium (MTT) method. ExperimentalMaterials The ligand HL (isoeuxanthone, namely 1,6-dihydroxyxanthone) was prepared according to the literature 16) with some improvement. All the chemicals were reagent grade and were used without further purification. Calf thymus DNA (ct DNA) and ethidium bromide (EB) were obtained from Sigma Chemical Co. All the measurements involving the interactions of the two complexes with ct DNA were carried out in doubly distilled water buffer containing 5 mM Tris[Tris(hydroxymethyl)-aminomethane] and 50 mM NaCl, and adjusted to pH 7.1 with hydrochloric acid. UV-Vis spectrometer was employed to check a solution of ct DNA purity (A 260 : A 280 Ͼ1.80) and the concentration (eϭ6600 M Ϫ1 cm Ϫ1 at 260 nm) in the buffer. 17,18)Physical Measurements Elemental analyses were conducted using an Elementar Vario EL elemental analyzer. The metal contents of the complexes were determined by titration with EDTA (ethylenediamine tetraacetic acid). Infrared ...

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“…The results also suggested that 2 had more significant cytotoxic activities than 1 against the human cancer cell lines and the inhibitory effect in vitro is consistent with the result of DNA binding studies above, which may be due to the complexes inducing DNA damage in cancer cells and the nature of the metal ions. [49][50][51] However, the complexes can also inhibit the normal human liver cell (L02), which needs to be further researched by modifying the ligands or other methods. Some more research are still in doing in our laboratory.…”

Section: Dna-binding Mode and Affinity Electronic Absorption Spectramentioning

confidence: 99%

Synthesis, Characterization, Cytotoxic Activities, and DNA-Binding Studies of Ternary Copper(II) Complexes with New Coumarin Derivatives

Jia

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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In this study, two novel complexes [Cu(MCVH)phen(H 2 O)] · ClO 4 (1) and [Cu(MCLH)phen(H 2 O)] · ClO 4 (2)(here, MCVH 2 ‫-7(؍‬hydroxy-4-methyl-8-coumarinyl) valine, MCLH 2 ‫-7(؍‬hydroxy-4-methyl-8-coumarinyl) leucine) have been synthesized and characterized by elemental analyses, molar conductance, infrared spectra (IR), 1 H-NMR and UV-Vis measurements. The interactions of them with calf thymus DNA (ct DNA) have been investigated by absorption spectroscopy, fluorescence spectroscopy, circular dichroism spectroscopy and viscosity measurements. Experimental results reveal an intercalative interaction with DNA for the complexes, furthermore the binding affinity of 2 is higher than that of 1 according to the calculated binding constant values. In addition, they were evaluated for their cytotoxic activities toward human prostate cancer cell (PC3), human liver cell (L02) and human myeloid leukemia cancer cell (HL-60) by acid phosphoatase assay. Both of them showed significant cytotoxic potency.Key words copper(II) complex; coumarin derivative; DNA-binding; intercalative mode; cytotoxic activity Chem. Pharm. Bull. 58(8) 1003-1008 (2010) © 2010 Pharmaceutical Society of Japan * To whom correspondence should be addressed. e-mail: tangn@lzu.edu.cn; wangqin329@yahoo.com.cn concentrations of 1 and 2 as constant at 10 mM while varying the concentration of ct DNA. Fitting was completed using an Origin 6.0 spreadsheet, where values of the binding constants K b were calculated.Fluorescence spectra of the competitive binding experiments were carried out by maintaining the EB and ct DNA concentration at 3 mM and 30 mM, respectively, while increasing the concentrations of the complexes. Fitting was completed using an Origin 6.0 spreadsheet, where values of K q were calculated.Viscosity experiments were carried out on an Ubbelodhe viscometer, immersed in a thermostated water-bath maintained at 25.0Ϯ0.1°C. Titrations were performed for the complexes (1-5 mM), and each compound was introduced into DNA solution (50 mM) present in the viscometer. Flow time was measured with a digital stopwatch and each sample was measured three times and an average flow time was calculated.The CD spectra of DNA were recorded on a Jasco J-810 spectropolarimeter at 25.0Ϯ0.1°C. Calf thymus DNA used were 120 mM in concentration and compounds solutions was added to a ratio of 1 : 1 (DNA/compound). Each sample solution was scanned in the range of 200-350 nm. CD spectrum was generated which represented the average of three scans from which the buffer background had been subtracted.Acid Phosphoatase Assay The reagent, p-nitrophenyl phosphate (p-NPP), was obtained from Amresco. The compounds synthesized were dissolved in dimethyl sulphoxide (DMSO) and diluted in culture medium. The final concentration of DMSO in cultures was always not exceeding 0.5% (v/v), which did not cause toxicity. The PC3 and HL-60 cells obtained from ATCC were maintained in Dulbecco's modified Eagle's medium (DMEM) medium with 10% fetal bovine serum (FBS), 100 U/ml penicillin and 10...

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Suppression of survival in human SKBR3 breast carcinoma in response to metal–chelator complexes is preferential for copper–dithiocarbamate

Cited by 25 publications

References 40 publications

Synthesis and characterization of the Zn(II) and Cu(II) piperidinyl isoeuxanthone complexes: DNA-binding and cytotoxic activity

Synthesis and characterization of the Zn(II) and Cu(II) piperidinyl isoeuxanthone complexes: DNA-binding and cytotoxic activity

Antitumor Activity and DNA-Binding Investigations of the Zn(II) and Cu(II) Complexes with Isoeuxanthone

Synthesis, Characterization, Cytotoxic Activities, and DNA-Binding Studies of Ternary Copper(II) Complexes with New Coumarin Derivatives

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