Synthesis, characterization, and biological studies of multidentate gold(<scp>i</scp>) and gold(<scp>iii</scp>) NHC complexes

Bauer, Elisabeth B.; Bernd, Marco A.; Schütz, Max; Oberkofler, Jens; Pöthig, Alexander; Reich, Robert M.; Kühn, Fritz E.

doi:10.1039/c9dt03183a

Cited by 24 publications

(18 citation statements)

References 58 publications

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“…At the beginning of the twenty-first century, gold(III) porphyrin complex, with satisfying physiological stability, was reported like promising anticancer agent with IC 50 values in the range of 0.73-0.11 µM. The studies against normal and cisplatin-resistant ovarian cancer have shown the ability of gold(III) porphyrin complex, in vitro and in vivo, to exceed cisplatin resistance without affecting health tissue (Lum et al, 2014;Bauer et al, 2019). Furthermore, carbamate-based Au(III) complexes were used for animal experiments and based on the observed data of clinical studies gave promising results of good anticancer effects (Marzano et al, 2011;Gu et al, 2019).…”

Section: Cytotoxic Activity Of Gold(iii) Complexesmentioning

confidence: 99%

Gold(III) Complexes: An Overview on Their Kinetics, Interactions With DNA/BSA, Cytotoxic Activity, and Computational Calculations

Radisavljević

Petrović

2020

Front. Chem.

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In the last few years, metallodrugs play a key role in the development of medicinal chemistry. The choice of metal ion, its oxidation state and stability, and the choice of inert and labile ligands are just some of the very important facts which must be considered before starting the synthesis of complexes with utilization in medicinal purpose. As a result, a lot of compounds of different transition metal ions found application for diagnostic and therapeutic purpose. Beside all, gold compounds have attracted particular attention. It is well-known that gold compounds could be used for the treatment of cancer, HIV, rheumatoid arthritis (chrysotherapy), and other diseases. This metal ion has unoccupied d-sublevels and possibility to form compounds with different oxidation states, from −1 to +5. However, gold(I) and gold(III) complexes are dominant in chemistry and medicine. Especially, gold(III) complexes are of great interest due to their structural similarity with cisplatin. Accordingly, this review summarizes the chemistry of some mononuclear and polynuclear gold(III) complexes. Special attention is given to gold(III) complexes with nitrogen-donor inert ligands (aliphatic or aromatic that have a possibility to stabilize complex) and their kinetic behavior toward different biologically relevant nucleophiles, mechanism of interaction with DNA/bovine serum albumin (BSA), cytotoxic activity, as well as computational calculations.

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Section: Cytotoxic Activity Of Gold(iii) Complexesmentioning

confidence: 99%

Gold(III) Complexes: An Overview on Their Kinetics, Interactions With DNA/BSA, Cytotoxic Activity, and Computational Calculations

Radisavljević

Petrović

2020

Front. Chem.

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“…In addition to the tetradentate porphyrin ligands, stabilization of the gold(III) ion can also be achieved by coordination with the tridentate (C ∧ N ∧ C, C ∧ N ∧ N or N ∧ C ∧ N) pincer ligand containing deprotonated C-donor atom(s) (C − ) and/or neutral σ-donating N-heterocyclic carbene (NHC) ligand(s), affording gold(III) complexes with high physiological stability and promising anticancer properties (Bertrand et al, 2017 ; Carboni et al, 2018 ; Bauer et al, 2019 ; Fares et al, 2020 ; Guarra et al, 2020 ). In this context, we have described the antitumor-active [Au III (C ∧ N ∧ C)(NHC)] + (H 2 C ∧ N ∧ C = 2,6-diphenylpyridine) complexes ( 5 and 6 ).…”

Section: Anticancer Cyclometalated Gold(iii) N-heterocyclic Carbene Cmentioning

confidence: 99%

Anticancer Gold(III) Compounds With Porphyrin or N-heterocyclic Carbene Ligands

Tong

Wan

et al. 2020

Front. Chem.

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The use of gold in medicine has a long history. Recent clinical applications include anti-inflammatory agents for the treatment of rheumatoid arthritis (chrysotherapy), and is currently being developed as potential anticancer chemotherapeutics. Gold(III), being isoelectronic to platinum(II) as in cisplatin, is of great interest but it is inherently unstable and redox-reactive under physiological conditions. Coordination ligands containing C and/or N donor atom(s) such as porphyrin, pincer-type cyclometalated and/or N-heterocyclic carbene (NHC) can be employed to stabilize gold(III) ion for the preparation of anticancer active compounds. In this review, we described our recent work on the anticancer properties of gold(III) compounds and the identification of molecular targets involved in the mechanisms of action. We also summarized the chemical formulation strategies that have been adopted for the delivery of cytotoxic gold compounds, and for ameliorating the in vivo toxicity.

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“…The performances of the dinuclear complexes, in terms of both activity and selectivity, were compared to their corresponding mononuclear counterparts and to dinuclear complexes not having carbohydrate-functionalized NHCs. Dinuclear Au(I) complexes with one or two bridging diNHC carbene ligands were reported to present anticancer properties, acting by inhibiting the thioredoxin reductase TrxR or by leading to mitochondria-induced apoptosis [24][25][26][27][28][29][30][31].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Studies on Dinuclear Gold(I) Complexes with Di-(N-Heterocyclic Carbene) Ligands Functionalized with Carbohydrates

et al. 2020

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The design of novel metal complexes with N-heterocyclic carbene (NHC) ligands that display biological activity is an active research field in organometallic chemistry. One of the possible approaches consists of the use of NHC ligands functionalized with a carbohydrate moiety. Two novel Au(I)–Au(I) dinuclear complexes were synthesized; they present a neutral structure with one bridging diNHC ligand, having one or both heterocyclic rings decorated with a carbohydrate functionality. With the symmetric diNHC ligand, the dicationic dinuclear complex bearing two bridging diNHC ligands was also synthesized. The study was completed by analyzing the antiproliferative properties of these complexes, which were compared to the activity displayed by similar mononuclear Au(I) complexes and by the analogous bimetallic Au(I)–Au(I) complex not functionalized with carbohydrates.

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Synthesis, characterization, and biological studies of multidentate gold(i) and gold(iii) NHC complexes

Abstract: The synthesis and characterization of a novel macrocyclic Au(iii) N-heterocyclic carbene (NHC) complex, a novel macrocyclic tetra-NHC benzimidazole ligand, and the corresponding Ag(i) and Au(i) complexes and initial biological studies are presented.

Cited by 24 publications

References 58 publications

Gold(III) Complexes: An Overview on Their Kinetics, Interactions With DNA/BSA, Cytotoxic Activity, and Computational Calculations

Gold(III) Complexes: An Overview on Their Kinetics, Interactions With DNA/BSA, Cytotoxic Activity, and Computational Calculations

Anticancer Gold(III) Compounds With Porphyrin or N-heterocyclic Carbene Ligands

Synthesis and Biological Studies on Dinuclear Gold(I) Complexes with Di-(N-Heterocyclic Carbene) Ligands Functionalized with Carbohydrates

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