Synthesis, characterization, spectral studies and cytotoxic effects of mixed-ligand mono and binuclear copper(II) complexes and their amide ligands

Abdolmaleki, Sara; Ghadermazi, Mohammad; Fattahi, Ali; Sheshmani, Shabnam

doi:10.1016/j.ica.2016.01.016

Cited by 44 publications

(7 citation statements)

References 52 publications

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“…The absorbance at a wavelength of 570 nm was then determined using a microplate reader (Bio-Rad, USA). The results were expressed as the dose that inhibited growth of the control by 50 % (IC 50 ) using a log10 plot of the drug concentration against the percentage of viable cells [11]. Tests were performed quintuplicate, and the mean inhibition (H) data were calculated using Eq 2.…”

Section: Cytotoxicity Assaymentioning

confidence: 99%

Biological activities and phenolic contents of <i>Argania spinosa</i> L (Sapotaceae) leaf extract

Dakiche¹,

Khali²,

Abu-el-Haija³

et al. 2017

Trop. J. Pharm Res

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Purpose: To investigate the phenolic profile and biological activities of Argania spinosa L. leaves. Methods: The crude methanol extract of leaves of A. spinosa L. Skeels was obtained by ultrasonic extraction, and the total polyphenolic and flavonoid contents were determined by ultra-high performance liquid chromatography-electrospray ionization-quadrupole time-of-flight-mass spectrometry (UPLC-ESI-QTOF-MS). In vitro antioxidant activity was determined by 2,2-di-phenyl-1-picryl-hydrazil (DPPH) radical myrecitin-3-galactoside, myrecitin-3-gluctoside, myrecitin-3-xyloside, quercetin-3-galactoside, quercetin-3-glucoside, quercetin-3-arabinofuranoside, and quercetin-3-rhamnoside

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Section: Cytotoxicity Assaymentioning

confidence: 99%

Biological activities and phenolic contents of <i>Argania spinosa</i> L (Sapotaceae) leaf extract

Dakiche¹,

Khali²,

Abu-el-Haija³

et al. 2017

Trop. J. Pharm Res

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“…After the report that [Cu(phen) 2 ] + complex cleaves DNA, a great number of copper complexes with N,N-donors ligands have been synthesized and utilized as artificial nucleases [1]. Moreover, many of these copper compounds have been described to inhibit tumoral cell growth [2][3][4][5][6][7][8][9][10][11][12][13][14]. Regarding the clinical utility of these complexes, two of them devel-oped by L. Ruiz and co-workers, are already approved for clinical trials as antitumor drugs [15,16].…”

Section: Introductionmentioning

confidence: 99%

Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies

Paixão

Marzano

Jaimes

et al. 2017

Journal of Inorganic Biochemistry

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Five new copper(II) complexes of the type [Cu(NO)(NN)(ClO)], in which NO=4-fluorophenoxyacetic acid hydrazide (4-FH) or 4-nitrobenzoic hydrazide (4-NH) and NN=1,10-phenanthroline (phen), 4-4'-dimethoxy-2-2'-bipyridine (dmb) or 2,2-bipyridine (bipy) were synthesized and characterized using various spectroscopic methods. The X-ray structural analysis of one representative compound indicates that the geometry around the copper ion is distorted octahedron, in which the ion is coordinated to hydrazide via the terminal nitrogen and the carbonyl oxygen, and to heterocyclic bases via their two nitrogen atoms. Two perchlorate anions occupy the apical positions, completing the coordination sphere. The cytotoxic activity of compounds was investigated in three tumor cell lines (K562, MDA-MB-231 and MCF-7). Concerning K562 cell line, the complexes with 1,10-phenanthroline exhibit high cytotoxic activity and are more active than carboplatin, free ligands and [Cu(phen)]. Considering the cytotoxicity results, further investigations for the compounds [Cu(4-FH)(phen)(ClO)] I and [Cu(4-NH)(phen)(ClO)]∙HO III were performed. Flow cytometric analysis revealed that these complexes induce apoptotic cell death in MDA-MB-231 cell line and bind to DNA with K values of 4.38×10 and 2.62×10, respectively. These compounds were also evaluated against wild type Mycobacterium tuberculosis (ATCC 27294) and exhibited antimycobacterial activity, displayed MIC values lower than those of the corresponding free ligands.

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“…The strongest hydrogen bonds seem to be N(2)–H(2)···O(11) [ x − 1, y, z ] and O(5 W)–H(5WB)···O(8 W) [ − x + 1, − y + 1, − z ] for C1; and O(5B)–H(5B)···O(1 W) and O(12 W)–H(12A)···O(2D) [ x + 1, y, z + 1 ] for C2. These interactions lead to the appearance of cyclic hydrogen bonding synthons as R (16), R (10) and R (8) for C1 (Figure S2b); and R (8), R (8) and R (8) for C2 (Figure S3b) 24 .…”

Section: Resultsmentioning

confidence: 99%

Novel Tl(III) complexes containing pyridine-2,6-dicarboxylate derivatives with selective anticancer activity through inducing mitochondria-mediated apoptosis in A375 cells

Abdolmaleki

Ghadermazi

Aliabadi

2021

Sci Rep

Self Cite

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Three novel Tl(III) complexes (C1), (C2) and (C3) were synthesized using the one-pot reactions of pyridine dicarboxylic acid derivatives, 2-aminobenzimidazole and/or 4-aminopyridine, and also thallium(III) nitrate trihydrate metal salt. The structure of all three complexes was determined by the single-crystal X-ray diffraction. C1 and C2 were realized to be isostructural with disordered square anti-prismatic geometry and for C3 arrangement of the distorted tricapped triangular prism was proposed. Cyclic voltammetry measurements on the complexes exhibited that formal potential values are more positive for C1 (E0ˊ 0.109 V) and C3 (E0ˊ 0.244 V) compared to C2 (E0ˊ –0.051 V), versus Ag/AgCl under argon. Moreover, cytotoxicity of the compounds was evaluated in vitro against two cancer cell lines including a human melanoma (A375), a human colon adenocarcinoma (HT29), and also one normal cell human foreskin fibroblast (HFF). The selective and potent cytotoxicity effect was exhibited by C1 and C3 on cancer cell lines. The apoptosis through a caspase-dependent mitochondrion pathway was confirmed by ROS production, MMP reduction, p53 activation, Bax up-regulation, and Bcl-2 down-regulation, cytochrome c release, procaspase-9, and 3 expression, for A375 cells treated to C1 and C3. According to similar cellular uptake of the complexes in A375 cell line, the generation of ROS was considered as an effective agent to justify the inhibition effect C1 and C3 on mentioned cells. Furthermore, arresting the cell cycle in the G2-M phase and inducing apoptosis were indicated by these two complexes.

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Synthesis, characterization, spectral studies and cytotoxic effects of mixed-ligand mono and binuclear copper(II) complexes and their amide ligands

Cited by 44 publications

References 52 publications

Biological activities and phenolic contents of <i>Argania spinosa</i> L (Sapotaceae) leaf extract

Biological activities and phenolic contents of <i>Argania spinosa</i> L (Sapotaceae) leaf extract

Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies

Novel Tl(III) complexes containing pyridine-2,6-dicarboxylate derivatives with selective anticancer activity through inducing mitochondria-mediated apoptosis in A375 cells

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