Tumor cytotoxicity of 5,6-dimethyl-1,10-phenanthroline and its corresponding gold(III) complex

Wein, Alexander N.; Stockhausen, Adam T; Hardcastle, Kenneth I.; Saadein, M. R.; Peng, Shifang; Wang, Dongsheng; Shin, Dong M.; Chen, Zhuo Georgia; Eichler, Jack F.

doi:10.1016/j.jinorgbio.2011.01.006

Cited by 60 publications

(27 citation statements)

References 20 publications

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“…Though a wide variety of organic-based molecular compounds have been used to treat tumors, the metallotherapy cisplatin is one of the most successful anti-cancer drugs. Despite its success, cisplatin therapy has several drawbacks, including the development of resistance to the drug by tumors and the occurrence of severe side-effects during treatment [1]. It is well known that gold (III) complexes are potential alternatives to the platinum (II) based drugs [2].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and stability of iron (III) complex ions possessing phenanthroline-based ligands

Tosonian¹,

Ruiz²,

Rios³

et al. 2013

OJIC

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It has previously been demonstrated that phenanthroline-based ligands used to make gold metallotherapuetics have the ability to exhibit cytotoxicity when not coordinated to the metal center. In an effort to help assess the mechanism by which these ligands may cause tumor cell death, iron binding and removal experiments have been considered. The close linkage between cell proliferation and intracellular iron concentrations suggest that iron deprivation strategies may be a mechanism involved in inhibiting tumor cell growth. With the creation of iron (III) phen complexes, the iron binding abilities of three polypyridal ligands [1,10-phenanthroline (phen), 2,9-dimethyl-1, 10-phenanthroline (methylphen), and 2,9-di-sec-butyl-1, 10-phenanthroline (sec-butylphen)] can be tested via a competition reaction with a known iron chelator. Therefore, iron (III) complexes possessing all three ligands were synthesized. Initial mass spectrometric and infrared absorption data indicate that iron (III) tetrachloride complex ions with protonated phen ligands (RphenH+) were formed: [phenH][FeCl4], [methylphenH][FeCl4], [sec-butylphenH][FeCl4]. UV-Vis spectroscopy was used to monitor the stability of the complex ions, and it was found that the sec-butylpheniron complex was more stable than the phen and methylphen analogues. This was based on the observation that free ligand was observed immediately upon the addition of EDTA to the [phenH][FeCl4] and [methylphenH] [FeCl4] complex ions.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and stability of iron (III) complex ions possessing phenanthroline-based ligands

Tosonian¹,

Ruiz²,

Rios³

et al. 2013

OJIC

Self Cite

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“…Some gold(I) complexes, such as auranofin and aurothiomalate, have been used very successfully in the treatment of rheumatoid arthritis [2], while gold(III) complexes have gained considerable attention as potential antitumor agents [3]. During the recent years, a large number of gold(III) complexes, in which the reduction potential of the Au(III) was lowered by the use of polydentate ligands, have been reported to be appreciably stable under physiologically relevant conditions and to manifest relevant cytotoxic activity against different human tumor cell lines [4][5][6][7][8][9][10][11][12][13][14][15][16]. The possible involvement of gold(III) complexes in cancer treatment initiated an interest in the area of gold(III) interactions with different biologically important ligands, such as amino acids and peptides [17].…”

Section: Introductionmentioning

confidence: 99%

Oxidation of methionine residue in Gly-Met dipeptide induced by [Au(en)Cl2]+ and influence of the chelated ligand on the rate of this redox process

et al. 2013

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“…Although it is well known that 1,10-phenanthroline is the parent of an important class of chelating agents and has structural features such as a rigid planar, hydrophobic, and its electron-poor heteroaromatic system whose nitrogen atoms are beautifully placed to act cooperatively in cation binding, in the literature, a few studies have reported on its anticancer activity. A gold complex with 6,6-dimethyl-1,10-phenanthroline was synthesized and characterized, and DNA binding and cytotoxic activities were determined [46]. Recently, a phenanthrolin-dicarbocylate ester has been found to show promising anticancer activity with selective DNA-binding activity against several human cancer cell lines [47].…”

Section: Discussionmentioning

confidence: 99%

Gold(III) compounds-mediated inhibition of lung cancer cell proliferation

Bostancıoğlu

Kaya²,

Koparal³

et al. 2016

Anti-Cancer Drugs

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Research on chemotherapeutics for lung cancer is crucial for designing a new therapeutic strategy against malignant lung tumors. Although radiotherapy and chemotherapy, which are not selective for cancer cells and exert toxic effects on healthy cells, have a limited advantage, they are the primary treatment modalities for non-small lung cancer. In addition to cytotoxicity, resistance of chemotherapeutics results in failure of treatment. This is why it is of utmost importance to focus on the creation of new chemotherapeutics without toxicity for the successful treatment and improved survival of cancer patients. New gold(III) and Pt(II) compounds were synthesized with a heterocyclic ligand using 2-phenylimidazo[4,5-f][1,10]phenanthroline as a ligand and bis-1,4-di[([1,10] phenanthroline-5-il)amino]-2-buten as a bridge molecule. The characterization of the compounds was carried out using a variety of spectroscopic methods (H NMR, IR, MS, and elemental analysis). Their antiproliferative, antitumoral, and apoptotic activities were determined. IR spectra and NMR results confirmed the formation of dinuclear heterocyclic complexes for two metal complexes. Cytotoxicity studies on lung cancer cells (A549) and healthy cells (CHL) showed a marked increase in cytotoxicity with the use of gold(III) complexes, and especially [Au(L)B](PF6)2 showed higher cytotoxic and apoptotic features than cisplatin at lower concentrations in cancer cells. These findings have been supported by results from DAPI staining and colorimetric measurement of the caspase-3 enzyme in both cell lines. Compounds showed selective toxicity on the cancer cells. In the light of the high efficacy of our newly synthesized gold complexes, they might be good and promising anticancer agents compared with cisplatin.

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Tumor cytotoxicity of 5,6-dimethyl-1,10-phenanthroline and its corresponding gold(III) complex

Cited by 60 publications

References 20 publications

Synthesis, characterization, and stability of iron (III) complex ions possessing phenanthroline-based ligands

Synthesis, characterization, and stability of iron (III) complex ions possessing phenanthroline-based ligands

Oxidation of methionine residue in Gly-Met dipeptide induced by [Au(en)Cl2]+ and influence of the chelated ligand on the rate of this redox process

Gold(III) compounds-mediated inhibition of lung cancer cell proliferation

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