Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N′-diacetate

Pantelić, Nebojša; Zmejkovski, Bojana B.; Trifunović-Macedoljan, Jelena; Savić, Andrija; Stanković, Dalibor M.; Damjanović, Ana; Juranić, Zorica D.; Kaluđerović, Goran N.; Sabo, Tibor J.

doi:10.1016/j.jinorgbio.2013.08.002

Cited by 21 publications

(20 citation statements)

References 54 publications

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“…Herein examined gold(III) complexes have shown lower activity against Fem-x, LS174T and A549 than on human cervix adenocarcinoma HeLa and human myelogenous leukemia K562 tumor cell lines, reported previously (22). Furthermore, it is important to note that the investigated complexes showed less toxic action against non-cancerous MRC-5 cells than on rested and stimulated normal immuUnauthenticated Download Date | 5/12/18 9:42 AM nocompetent human peripheral blood mononuclear cells (PBMC) (22). This data point out that investigations concerning anticancer agents development require studies in diverse types of normal cells.…”

Section: Discussionmentioning

confidence: 60%

“…Additionally, on adherent cell lines complexes 1-6 exhibit significantly lower antitumor activity than on the nonadherent leukemic K562 cells (22). On the other hand, according to the rapidly dividing HeLa and Fem-x cells all complexes show a very similar, somewhat greater cytotoxicity (22).…”

Section: Discussionmentioning

confidence: 95%

“…Shortly, Na[AuCl 4 ] was reacted with with an equimolar amount of corresponding ligands, methyl, ethyl, n-propyl, n-butyl, isobutyl and isoamyl esters of (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid resprectively (22) …”

Section: Complexesmentioning

confidence: 99%

“…Since gold(III) is isoelectronic to platinum(II) and both metals preferentially generate square planar complexes (d 8 system) a number of gold(III) complexes were synthesized and tested as an alternative to the anticancer drug cisplatin (22)(23)(24)(25)(26)(27). Due to the fact that the gold(III) has high reduction potential, a range of strategies has been applied in order to obtain gold(III) complexes with sufficient stability under physiologically relevant conditions.…”

Section: Introductionmentioning

confidence: 99%

“…The in vitro cytotoxic evaluation of the investigated complexes against tumor cell lines: human adenocarcinoma HeLa, human myelogenous leukemia K562 and against normal stimulated and nonstimulated peripheral blood mononuclear cells PBMC, showed that the cytotoxic action of gold(III) complexes with cyclohexyl-functionalized ethylenediamine-N,N'-diacetate esters, (R= i-Bu, i-Am), is fairly comparable to that of cisplatin (22). Additionally, it was found that these complexes reduce to gold(I) species in two steps through short-living intermediate gold(II) (35).…”

Section: Introductionmentioning

confidence: 99%

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Antiproliferative Activity of Gold(III) Complexes with Esters of Cyclohexyl-Functionalized Ethylenediamine-N,N’-Diacetate

Pantelić

Stanojković

Zmejkovski

et al. 2017

Serbian Journal of Experimental and Clinical Research

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Six gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N'-diacetate, general formula [AuCl 2 {(S,S)-R 2 eddch}]PF 6 , [(S,S)-eddch = (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = Me, Et,[1][2][3][4][5][6], respectively], were tested against cancer cell lines such as human melanoma Fem-x, human colon carcinoma LS174T and non-small cell lung carcinoma A549 as well as a non-cancerous human embryonic lung fi broblasts [3][4] SAŽETAK Šest kompleksa zlata(III) sa cikloheksil-funkcionalizovanim estrima etilendiamin-N,N'-diacetata, opšte formule [AuCl 2 {(S,S)-R 2 eddch}]PF 6 , ((S,S)-eddch = (S,S)-etilendiamin-N,N'-di-2-(3-cicloheksil)propanoat, R = Me, Et, n-Pr, n-Bu, i-Bu, i-Am, 1-6), ispitivano je na humanim ćelijskim linijama malignog melanoma Fem-x, karcinoma debelog creva LS174T, karcinoma pluća A549 kao i normalnim ćeli-jama MRC-5 (fetalni plućni fi broblast) korišćenjem

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Section: Discussionmentioning

confidence: 60%

Section: Discussionmentioning

confidence: 95%

Section: Complexesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Antiproliferative Activity of Gold(III) Complexes with Esters of Cyclohexyl-Functionalized Ethylenediamine-N,N’-Diacetate

Pantelić

Stanojković

Zmejkovski

et al. 2017

Serbian Journal of Experimental and Clinical Research

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New gold(III) chlorophenyl terpyridine complex: Biomolecular interactions and anticancer activity against human oral squamous cell carcinoma

Radisavljević

Kesić

Ćoćić

et al. 2022

Applied Organom Chemis

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In this work we synthesized new monofunctional gold(III) complex [Au(Cl‐Ph‐tpy)Cl]Cl2 (Cl‐Ph‐tpy = 4′‐[4‐chlorophenyl]‐2,2′:6′, 2″‐terpyridine). This complex was characterized by UV–Vis, NMR, IR, and ESI‐MS spectrometry. The kinetic study of the substitution reactions of the Au‐Cl‐Ph‐tpy complex with biomolecules showed that the rate constants depend on the nature of the entering nucleophile. Based on the calculated values of entropy (∆H≠ > 0) and enthalpy (∆S≠ < 0) the proposed substitution mechanism is associative. Additionally, the relative stability and thermodynamic properties of Au‐Cl‐Ph‐tpy complex were compared with the analogue Au‐tpy complex by the B3LYP/def2‐svp method. DNA/BSA binding studies showed that Au‐Cl‐Ph‐tpy complex interacts with CT DNA through the intercalation and moderately quenches the fluorescence of tryptophan residues in serum albumin (BSA). Molecular docking confirmed results obtained by spectroscopic experiments and suggested site I (subdomain IIA) for binding of Au complex to BSA. We demonstrated that the Au chlorophenyl terpyridine complex possessed significant in vitro cytotoxic activity against human oral squamous carcinoma cells (CAL‐27), induced apoptosis, inhibited proliferation of CAL‐27 cells, and induced cell cycle disturbance. Treatment of CAL‐27 cells with the Au complex enhanced expression of cyclin‐dependent kinase inhibitors p21 and p27, resulting in cell cycle arrest in the G1 phase, reduced the percentage of CAL‐27 cells in S phase and decreased expression of Ki‐67. Additionally, Au complex reduced expression of phosphorylated STAT3 and downstream regulated molecules associated with cancer stemness, NANOG, and Sox2 protein.

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Reactions of cytotoxic metallodrugs with lysozyme in pure DMSO explored through UV–Vis absorption spectroscopy and ESI MS

et al. 2015

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The reactions of four representative metallodrugs with the model protein HEWL were investigated within a non-aqueous environment-i.e. in pure DMSO- through UV-Vis absorption spectroscopy and ESI MS analysis. Notably, formation of a variety of metallodrug-protein adducts was clearly documented. This is the first example for this kind of protein metalation reactions carried out within a pure organic solvent. It is shown that the applied solution conditions greatly affect the nature of the formed adducts, this being well accounted for by the fact that the overall protein conformation is greatly perturbed within pure DMSO; in addition, the activation profiles of the studied metallodrugs are also highly dependent on the nature of the solvent. The implications of these results are discussed.

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Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N′-diacetate

Cited by 21 publications

References 54 publications

Antiproliferative Activity of Gold(III) Complexes with Esters of Cyclohexyl-Functionalized Ethylenediamine-N,N’-Diacetate

Antiproliferative Activity of Gold(III) Complexes with Esters of Cyclohexyl-Functionalized Ethylenediamine-N,N’-Diacetate

New gold(III) chlorophenyl terpyridine complex: Biomolecular interactions and anticancer activity against human oral squamous cell carcinoma

Reactions of cytotoxic metallodrugs with lysozyme in pure DMSO explored through UV–Vis absorption spectroscopy and ESI MS

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