Synthesis and characterization of new biologically active palladium(II) complexes with (1E,6E)-1,7-bis(3,4-diethoxyphenyl)-1,6-heptadiene-3,5-dione

Miklášova, Natalia; Fischer‐Fodor, Eva; Mikláš, Roman; Kucková, Lenka; Kožı́šek, Jozef; Liptaj, Tibor; Şoriţău, Olga; Valentová, Jindra; Devı́nsky, Ferdinand

doi:10.1016/j.inoche.2014.06.006

Cited by 19 publications

(15 citation statements)

References 16 publications

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“…The compounds potential for auto-fluorescence and colour background was tested. The cytotoxicity of the compounds was assessed using the MTT colorimetric method [ 37 ]; the IC 50 parameter was calculated from the dose-response curve (GraphPad Prism 5 software, version 5, GraphPad Company, San Diego, CA, USA).…”

Section: Methodsmentioning

confidence: 99%

Novel Thiazolo[5,4-b]phenothiazine Derivatives: Synthesis, Structural Characterization, and In Vitro Evaluation of Antiproliferative Activity against Human Leukaemia

Brém

Gál

Găină

et al. 2017

IJMS

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The molecular frame of the reported series of new polyheterocyclic compounds was intended to combine the potent phenothiazine and benzothiazole pharmacophoric units. The synthetic strategy applied was based on oxidative cyclization of N-(phenothiazin-3-yl)-thioamides and it was validated by the preparation of new 2-alkyl- and 2-aryl-thiazolo[5,4-b]phenothiazine derivatives. Optical properties of the series were experimentally emphasized by UV-Vis absorption/emission spectroscopy and structural features were theoretically modelled using density functional theory (DFT). In vitro activity as antileukemic agents of thiazolo[5,4-b]phenothiazine and N-(phenothiazine-3-yl)-thioamides were comparatively evaluated using cultivated HL-60 human promyelocytic and THP-1 human monocytic leukaemia cell lines. Some representatives proved selectivity against tumour cell lines, cytotoxicity, apoptosis induction, and cellular metabolism impairment capacity. 2-Naphthyl-thiazolo[5,4-b]phenothiazine was identified as the most effective of the series by displaying against THP-1 cell lines a cytotoxicity close to cytarabine antineoplastic agent.

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Section: Methodsmentioning

confidence: 99%

Novel Thiazolo[5,4-b]phenothiazine Derivatives: Synthesis, Structural Characterization, and In Vitro Evaluation of Antiproliferative Activity against Human Leukaemia

Brém

Gál

Găină

et al. 2017

IJMS

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“…Curcumin derivative 1,7-bis(2-methoxyphenyl)hepta-1,6-diene-3,5-dione was prepared according to a known procedure [ 47 ]. The precursor palladium complexes with ( R , R )- N , N , N ′, N ′-tetramethylcyclohexane-1,2-diamine[(C 10 H 22 N 2 )Pd(OAc) 2 ] and with 1,4-dimethylpiperazine[(C 6 H 14 N 2 )Pd(OAc) 2 ] were synthesized based on a procedure reported on our previous studies [ 29 ].…”

Section: Methodsmentioning

confidence: 99%

“…Although platinum and palladium complexes are commonly used in the cancer therapy [ 22 ], those containing curcumin or curcumin’s analogues also proved to be effective as antitumor agents [ 23 , 24 , 25 , 26 , 27 ]. In former studies, we had the confirmation of efficiency of metal complexes of curcumin concerning the antineoplastic activity in ovarian, colorectal, melanoma, cervical, liver and breast carcinomas [ 28 , 29 , 30 ], a fact that encouraged us to further investigations of such coordination models. Curcumin acts against cancer stem cells by interferences with several signaling pathways [ 31 ], and the coordination of curcumin and its analogues to metals may increase the selectivity for biological targets and improve their bioavailability levels in tumor cells [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Novel Palladium(II) Complexes that Influence Prominin-1/CD133 Expression and Stem Cell Factor Release in Tumor Cells

et al. 2017

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New Pd(II) complexes of 1,7-bis(2-methoxyphenyl)hepta-1,6-diene-3,5-dione were synthesized and structurally characterized. The complexes were tested in vitro on human colon and hepatic carcinoma cell lines, normal hepatic cells and hematopoietic progenitor cells. Biological tests proved that Pd(II) complexes 1 and 2 (containing a curcumin derivative) exhibit a strong in vitro antitumor effect against the cells derived from human colorectal carcinoma and the hepatic metastasis of a colorectal carcinoma. Complex 1 has an outstanding inhibitory effect against BRAF-mutant colon carcinoma and hepatocarcinoma cell growth; 1 and 2 are both more active than the free ligand and have the capacity to trigger early apoptotic processes. By flow cytometric measurements, an important decrease of prominin-1 (CD133) molecule expression on tumor cells membrane was identified in cell populations subjected to 1 and 2. Quantitative immune enzymatic assay proved restrictions in stem cell factor (SCF) release by treated tumor cells. Although less cytotoxic, the free ligand inhibits the surface marker CD133 expression in hepatocarcinoma cells, and in HT-29 colon carcinoma. The new synthesized Pd(II) complexes 1 and 2 exhibit an important potential through their selective cytotoxic activity and by targeting the stem-like tumor cell populations, which leads to the tumor growth arrest and prevention of metastasis.

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“…Palladium(II) complexes 1 and 2 containing bisdemethoxycurcumin have been synthesized following a previously reported method [30][31][32][33] which consists of reacting the corresponding intermediate palladium(II) complexes with bisdemethoxycurcumin in an equimolecular ratio (Scheme 1). The two intermediate complexes were prepared from palladium(II) acetate and N,N,N ,N -tetramethylcycohexane-1,2-diamine and N,Ndimethylpiperazine, respectively [30]. Spectral methods ( 1 H-and 13 C-NMR, HR-MS and IR) confirmed the proposed structural formulas of compounds 1 and 2.…”

Section: Preparation and Structural Characterization Of Palladium(ii) Complexesmentioning

confidence: 99%

Evaluation of Antiproliferative Palladium(II) Complexes of Synthetic Bisdemethoxycurcumin towards In Vitro Cytotoxicity and Molecular Docking on DNA Sequence

et al. 2021

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Metallodrugs form a large family of therapeutic agents against cancer, among which is cisplatin, a paradigmatic member. Therapeutic resistance and undesired side effects to Pt(II) related drugs, prompts research on different metal–ligand combinations with potentially enhanced biological activity. We present the synthesis and biological tests of novel palladium(II) complexes containing bisdemethoxycurcumin (BDMC) 1 and 2. Complexes were fully characterized and their structures were determined by X-ray diffraction. Their biological activity was assessed for several selected human tumor cell lines: Jurkat (human leukaemic T-cell lymphoma), HCT-116 (human colorectal carcinoma), HeLa (human cervix epitheloid carcinoma), MCF-7 (human breast adenocarcinoma), MDA-MB-231 (human mammary gland adenocarcinoma), A549 (human alveolar adenocarcinoma), Caco-2 (human colorectal carcinoma), and for non-cancerous 3T3 cells (murine fibroblasts). The cytotoxicity of 1 is comparable to that of cisplatin, and superior to that of 2 in all cell lines. It is a correlation between IC50 values of 1 and 2 in the eight studied cell types, promising a potential use as anti-proliferative drugs. Moreover, for Jurkat cell line, complexes 1 and 2, show an enhanced activity. DFT and docking calculations on the NF-κB protein, Human Serum Albumin (HSA), and DNA were performed for 1 and 2 to correlate with their biological activities.

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Synthesis and characterization of new biologically active palladium(II) complexes with (1E,6E)-1,7-bis(3,4-diethoxyphenyl)-1,6-heptadiene-3,5-dione

Cited by 19 publications

References 16 publications

Novel Thiazolo[5,4-b]phenothiazine Derivatives: Synthesis, Structural Characterization, and In Vitro Evaluation of Antiproliferative Activity against Human Leukaemia

Novel Thiazolo[5,4-b]phenothiazine Derivatives: Synthesis, Structural Characterization, and In Vitro Evaluation of Antiproliferative Activity against Human Leukaemia

Novel Palladium(II) Complexes that Influence Prominin-1/CD133 Expression and Stem Cell Factor Release in Tumor Cells

Evaluation of Antiproliferative Palladium(II) Complexes of Synthetic Bisdemethoxycurcumin towards In Vitro Cytotoxicity and Molecular Docking on DNA Sequence

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