Structures and biochemical evaluation of silver(I) 5,5-diethylbarbiturate complexes with bis(diphenylphosphino)alkanes as potential antimicrobial and anticancer agents

Yılmaz, Veysel T.; İçsel, Ceyda; Batur, Jenaidullah; Aydınlık, Şeyma; Şahintürk, Pınar; Aygün, Muhıttın

doi:10.1016/j.ejmech.2017.08.062

Cited by 32 publications

(15 citation statements)

References 51 publications

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“… a Data measured by us, under the same conditions as those for the other compounds. b Data taken from ref . c Data taken from ref , where authors studied several strains of P. aeruginosa . MICs were transformed by us from milligrams per milliliter to micromolars. d Not determined. …”

Section: Results and Discussionmentioning

confidence: 99%

(Amino)cyclophosphazenes as Multisite Ligands for the Synthesis of Antitumoral and Antibacterial Silver(I) Complexes

et al. 2020

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The reactivity of the multisite (amino)cyclotriphosphazene ligands, [N3P3(NHCy)6] and [N3P3(NHCy)3(NMe2)3], has been explored in order to obtain silver(I) metallophosphazene complexes. Two series of cationic silver(I) metallophosphazenes were obtained and characterized: [N3P3(NHCy)6{AgL} n ](TfO) n [n = 2, L = PPh3 (2), PPh2Me (4); n = 3, L = PPh3 (3), PPh2Me (5), TPA (TPA = 1,3,5-triaza-7-phosphaadamantane, 6)] and nongem-trans-[N3P3(NHCy)3(NMe2)3{AgL} n ](TfO) n [n = 2, L = PPh3 (7), PPh2Me (9); n = 3, L = PPh3 (8), PPh2Me (10)]. 5, 7, and 9 have also been characterized by single-crystal X-ray diffraction, thereby allowing key bonding information to be obtained. Compounds 2–6, 9, and 10 were screened for in vitro cytotoxic activity against two tumor human cell lines, MCF7 (breast adenocarcinoma) and HepG2 (hepatocellular carcinoma), and for antimicrobial activity against five bacterial species including Gram-positive, Gram-negative, and Mycobacteria strains. Both the IC50 and MIC values revealed excellent biological activity for these metal complexes, compared with their precursors and cisplatin and also AgNO3 and silver sulfadiazine, respectively. Both IC50 and MIC values are among the lowest values found for any silver derivatives against the cell lines and bacterial strains used in this work. The structure–activity relationships were clear. The most cytotoxic and antimicrobial derivatives were those with the triphenylphosphane and [N3P3(NHCy)6] ligands. A significant improvement in the activity was also observed upon a rise in the number of silver atoms linked to the phosphazene ring.

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Section: Results and Discussionmentioning

confidence: 99%

(Amino)cyclophosphazenes as Multisite Ligands for the Synthesis of Antitumoral and Antibacterial Silver(I) Complexes

et al. 2020

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“…myocrisin and auranofin, are used for the treatment of rheumatoid arthritis [5]. Notably, silver and its compounds [6,7] and silver-based nanoparticles [8] have long been known to possess strong inhibitory and bactericidal effects as well as a broad spectrum of anti-microbial activities for bacteria, fungi and viruses, and continue to attract significant attention [9][10][11][12]. Silver generally exhibits higher toxicity to microorganisms with lower toxicity to mammalian cells compared with other metals [13].…”

Section: Introductionmentioning

confidence: 99%

In vitro anti-bacterial and time kill evaluation of binuclear tricyclohexylphosphanesilver(I) dithiocarbamates, {Cy3PAg(S2CNRR′)}2

Tan

Yeo

et al. 2019

Journal of Inorganic Biochemistry

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Four binuclear phosphanesilver(I) dithiocarbamates, {cyclohexyl 3 PAg(S 2 CNRR′)} 2 for R = R′ = Et (1), CH 2 CH 2 (2), CH 2 CH 2 OH (3) and R = Me, R′ = CH 2 CH 2 OH (4) have been synthesised and characterised by spectroscopy and crystallography, and feature tri-connective, μ 2 -bridging dithiocarbamate ligands and distorted tetrahedral geometries based on PS 3 donor sets. The compounds were evaluated for anti-bacterial activity against a total of 12 clinically important pathogens. Based on minimum inhibitory concentration (MIC) and cell viability tests (human embryonic kidney cells, HEK 293), 1-4 are specifically active against Gram-positive bacteria while demonstrating low toxicity; 3 and 4 are active against methicillin resistant S. aureus (MRSA). Across the series, 4 was most effective and was more active than the standard anti-biotic chloramphenicol. Time kill assays reveal 1-4 to exhibit both time-and concentration-dependent pharmacokinetics against susceptible bacteria. Compound 4 demonstrates rapid (within 2 h) bactericidal activity at 1 and 2 × MIC to reach a maximum decrease of 5.2 log 10 CFU/mL against S. aureus (MRSA). While the R = Cy and Ph derivatives exhibited specific activity against Gram-positive bacteria, the R = Et compound showed broad range activity against both Gram-positive and Gram-negative bacteria [23]. Also, based on time kill studies the R = Cy and Ph compounds were bactericidal whereas the R = Et compound was bactericidal and

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“…In addition to the expected biological properties of PPTA, binding to Cu 2+ (Shahabadi et al, 2017;Jopp et al, 2017;Sanz Del Olmo et al, 2017;Mardani, Kazemshoar-Duzduzani et al, 2018;Saghatforoush et al, 2018) and Ag + (Rendošová et al, 2018;Fatima et al, 2017;Ş ahin-Bö lü kbaşı et al, 2019;Liang et al, 2018;Yilmaz et al, 2017) ions makes these complexes a good choice for biologically active compounds. For the study of the biological activities of PPTA and complexes 1 and 2, docking calculations were run to investigate the possibility of an interaction between these compounds with ten protein targets (Marandi, Moeini, Alizadeh, Mardani, Quah, Loh & Woollins, 2018;Mardani, Kazemshoar-Duzduzani et al, including BRAF kinase, Cathepsin B (CatB), DNA gyrase, Histone deacetylase (HDAC7), recombinant Human albumin (rHA), Ribonucleotide reductases (RNR), Thioredoxin reductase (TrxR), Thymidylate synthase (TS) and Topoisomerase II (Top II), along with B-DNA.…”

Section: Introductionmentioning

confidence: 99%

Coordination of a triazine ligand with Cu^II and Ag^I investigated by spectral, structural, theoretical and docking studies

Marandi¹,

Moeini²,

Krautscheid³

2019

Acta Crystallogr C

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Two complexes of 5‐phenyl‐3‐(pyridin‐2‐yl)‐1,2,4‐triazine (PPTA), namely (ethanol‐κO)bis(nitrato‐κO)[5‐phenyl‐3‐(pyridin‐2‐yl‐κN)‐1,2,4‐triazine‐κN2]copper(II), [Cu(NO3)2(C14H10N4)(C2H6O)] or [Cu(NO3)2(PPTA)(EtOH)] (1), and bis[μ‐5‐phenyl‐3‐(pyridin‐2‐yl)‐1,2,4‐triazine]‐κ3N1:N2,N3;κ3N2,N3:N1‐bis[(nitrato‐κO)silver(I)], [Ag2(NO3)2(C14H10N4)2] or [Ag2(NO3)2(μ‐PPTA)2] (2), were prepared and characterized by elemental analysis, FT–IR spectroscopy and single‐crystal X‐ray diffraction. The X‐ray structure analysis of 1 revealed a copper complex with square‐pyramdial geometry containing two O‐donor nitrate ligands along with an N,N′‐donor PPTA ligand and one O‐donor ethanol ligand. In the binuclear structure of 2, formed by the bridging of two PPTA ligands, each Ag atom has an AgN3O environment and square‐planar geometry. In addition to the four dative interactions, each Ag atom interacts with two O atoms of two nitrate ligands on adjacent complexes to complete a pseudo‐octahedral geometry. Density functional theory (DFT) calculations revealed that the geometry around the Cu and Ag atoms in 1opt and 2opt (opt is optimized) for an isolated molecule is the same as the experimental results. In 1, O—H…O hydrogen bonds form R12(4) motifs. In the crystal network of the complexes, in addition to the hydrogen bonds, there are π–π stacking interactions between the aromatic rings (phenyl, pyridine and triazine) of the ligands on adjacent complexes. The ability of the ligand and complexes 1 and 2 to interact with ten selected biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS, Top II and B‐DNA) was investigated by docking studies. The results show that the studied compounds can interact with proteins better than doxorubicin (except for TrxR and Top II).

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Structures and biochemical evaluation of silver(I) 5,5-diethylbarbiturate complexes with bis(diphenylphosphino)alkanes as potential antimicrobial and anticancer agents

Cited by 32 publications

References 51 publications

(Amino)cyclophosphazenes as Multisite Ligands for the Synthesis of Antitumoral and Antibacterial Silver(I) Complexes

(Amino)cyclophosphazenes as Multisite Ligands for the Synthesis of Antitumoral and Antibacterial Silver(I) Complexes

In vitro anti-bacterial and time kill evaluation of binuclear tricyclohexylphosphanesilver(I) dithiocarbamates, {Cy3PAg(S2CNRR′)}2

Coordination of a triazine ligand with Cu^II and Ag^I investigated by spectral, structural, theoretical and docking studies

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Structures and biochemical evaluation of silver(I) 5,5-diethylbarbiturate complexes with bis(diphenylphosphino)alkanes as potential antimicrobial and anticancer agents

Cited by 32 publications

References 51 publications

(Amino)cyclophosphazenes as Multisite Ligands for the Synthesis of Antitumoral and Antibacterial Silver(I) Complexes

(Amino)cyclophosphazenes as Multisite Ligands for the Synthesis of Antitumoral and Antibacterial Silver(I) Complexes

In vitro anti-bacterial and time kill evaluation of binuclear tricyclohexylphosphanesilver(I) dithiocarbamates, {Cy3PAg(S2CNRR′)}2

Coordination of a triazine ligand with CuII and AgI investigated by spectral, structural, theoretical and docking studies

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Coordination of a triazine ligand with Cu^II and Ag^I investigated by spectral, structural, theoretical and docking studies