Synthesis and biological evaluation of N-heterocyclic carbene–silver(I) acetate complexes derived from 4,5-ditolyl-imidazole

Hackenberg, Frauke; Lally, Grainne; Müller‐Bunz, Helge; Paradisi, Francesca; Quaglia, Daniela; Streciwilk, Wojciech; Tacke, Matthias

doi:10.1016/j.ica.2012.10.029

Cited by 48 publications

(31 citation statements)

References 35 publications

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“…So far, metal-NHC complexes have been mostly studied as new antibacterial and anticancer agents. Although research on anti-infectives has been largely focused on Ag I -NHC complexes, [8][9][10][11] Au I -NHC derivatives are the most studied examples concerning new anticancer agents. [12][13][14][15] This type of complex showed among other effects a strong and selective inhibition of the enzyme thioredoxin reductase (TrxR), induction of apoptosis, or depolarization of the mitochondrial membrane.…”

Section: Introductionmentioning

confidence: 99%

A Chemical–Biological Evaluation of Rhodium(I) N‐Heterocyclic Carbene Complexes as Prospective Anticancer Drugs

Oehninger

Küster

Schmidt

et al. 2013

Chemistry A European J

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Rhodium(I) complexes bearing N-heterocyclic carbene (NHC) ligands have been widely used in catalytic chemistry, but there are very few reports of biological properties of these organometallics. A series of Rh(I)-NHC derivatives with 1,5-cyclooctadiene and CO as secondary ligands were synthesized, characterized, and biologically investigated as prospective antitumor drug candidates. Pronounced antiproliferative effects were noted for all complexes, along with moderate inhibitory activity of thioredoxin reductase (TrxR) and efficient binding to biomolecules (DNA, albumin). Biodistribution studies showed that the presence of albumin lowered the cellular uptake and confirmed the transport of rhodium into the nuclei. Changes in the mitochondrial membrane potential (MMP) were observed as well as DNA fragmentation in wild-type and daunorubicin- or vincristine-resistant Nalm-6 leukemia cells. Overall, these studies indicated that Rh(I)-NHC fragments could be used as partial structures of new antitumor agents, in particular in those drugs designed to address resistant malignant tissues.

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Section: Introductionmentioning

confidence: 99%

A Chemical–Biological Evaluation of Rhodium(I) N‐Heterocyclic Carbene Complexes as Prospective Anticancer Drugs

Oehninger

Küster

Schmidt

et al. 2013

Chemistry A European J

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“…The anticancer activity of metal‐ N ‐heterocyclic carbenes (Ag(I), Au(I), Pd(II), and Cu(I)‐NHCs) have previously been reviewed (Biffis et al, ; Hackenberg, Lally, et al, ; Hackenberg, Müller‐Bunz, et al, ; Messori et al, ; Rana et al, ; Ray et al, ; Schuh et al, ; Siciliano et al, ; Teyssot et al, 2009; Teyssot, Jarrousse, Chevry, et al, ; Teyssot, Jarrousse, Manin, et al, ; Yan et al, ; Zou, Lum, Chui, & Che, ). In many cases, these metal complexes are capable of outperforming established platinum‐based antineoplastic drugs, such as cisplatin.…”

Section: Anticancer Activities Of Silver‐nhcmentioning

confidence: 99%

“…In the Caki‐1 (renal cancer) cell line the five new symmetrically substituted SCCs ( 35a ‐ e, Figure ) exhibited IC 50 values (3.0, 0.51, 4.2, 9.0, and 26 μM) and in MCF‐7 (breast cancer) cell line IC 50 values (2.3, 1.4, 3.0, 3.4, and 14 μM) (Hackenberg, Lally, et al, ; Hackenberg, Müller‐Bunz, et al, ). Comparing SBC3 (1,3‐bisbenzyl‐4,5‐bisphenyl‐imidazole‐2‐ylium silver(I) acetate) which has an IC 50 value of 14 (±1) μM in Caki‐1 and 5.8 (±0.6) μM in MCF‐7, these symmetrically substituted SCC compounds show improved activity in both cell lines.…”

Section: Anticancer Activities Of Silver‐nhcmentioning

confidence: 99%

“…The anticancer activity of metal-N-heterocyclic carbenes (Ag(I), Au(I), Pd(II), and Cu(I)-NHCs) have previously been reviewed (Biffis et al, 2009;Hackenberg, Lally, et al, 2013;Messori et al, 2014;Rana et al, 2014;Ray et al, 2007 In continuation, the same group reported the synthesis and biological characterization of two monodentate Ag-bis(NHC) complexes, bis(1,3-dimethylimidazol-2-ylidene) silver(I) nitrate (4) and bis(4,-5-dichloro-1,3-dimethylimidazol-2-ylidene) silver(I) nitrate (5) ( Figure 2) (Siciliano et al, 2011). The therapeutic properties were determined using lung cancer cells (H460).…”

Section: Anticancer Activities Of Silver-nhcmentioning

confidence: 99%

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Silver carbene complexes: An emerging class of anticancer agents

Kankala

Thota

Björkling

et al. 2018

Drug Development Research

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Cancer is a major global health problem with large therapeutic challenges. Although substantial progress has been made in cancer therapy, there still remains a need to develop novel and effective treatment strategies to treat several relapsed and refractory cancers. Recently, there has been growing demand for considering organometallics as antineoplastic agents. This review is focused on a group of organometallics, silver N‐heterocyclic carbene complexes (SCCs) and their anticancer efficacy in targeting multiple pathways in various in vitro cancer model systems. However, the precise molecular mechanism of SCCs anticancer properties remains unclear. Here, we discuss the SCCs chemistry, potential molecular targets, possible molecular mechanism of action, and their application in cancer therapies.

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“…So, more work needs to be carried out to understand the influence effects of such complexes. In addition, most silver complexes have shown interesting luminescence property [11][12][13] and biological activities [14][15][16][17] . Lung cancer is one of the most common and life-threatening malignancies worldwide.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Crystal Structure of a Polymeric Silver(i) Complex With Cytotoxic Property

Zhang

2015

J. Chil. Chem. Soc.

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A new polymeric silver(I) complex, [Ag 2 (L 1 ) 2 (L 2 )(OH 2 )] n , was obtained by the reaction of 3-aminopyrazine-2-carboxylic acid (HL 1 ), 2-amino-5-methylpyridine (L 2 ) and silver oxide in aqueous ammonia. The complex was characterized by elemental analysis, IR spectra and single crystal X-ray determination. The smallest repeat unit contains a [Ag 2 (L 1 ) 2 (L 2 )(OH 2 )] moiety. The Ag···Ag distance is 7.490(2) Å. One Ag atom is coordinated by three pyrazine N and two carboxylate O atoms from four L 1 ligands, forming a square pyramidal coordination, and the other one is coordinated by one pyrazine N and one carboxylate O atoms from a L 1 ligand, one pyridine N atom from a L 2 ligand, and one water O atom, forming a square planar geometry. In the crystal structure of the complex, the dinuclear silver moieties are linked through L 1 ligands, to form 1D chains along the x-axis direction. The chains are further linked through intermolecular hydrogen bonds in the y-and z-axis directions, forming a 3D network. In addition, there are π···π interactions among the chains. The complex showed effective cytotoxic property on human lung cancer cell line A549.

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Synthesis and biological evaluation of N-heterocyclic carbene–silver(I) acetate complexes derived from 4,5-ditolyl-imidazole

Cited by 48 publications

References 35 publications

A Chemical–Biological Evaluation of Rhodium(I) N‐Heterocyclic Carbene Complexes as Prospective Anticancer Drugs

A Chemical–Biological Evaluation of Rhodium(I) N‐Heterocyclic Carbene Complexes as Prospective Anticancer Drugs

Silver carbene complexes: An emerging class of anticancer agents

Synthesis, Characterization and Crystal Structure of a Polymeric Silver(i) Complex With Cytotoxic Property

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