Synthesis, characterization and biological activity of bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2<i>H</i>-imidazol-2-ylidene]gold(<scp>i</scp>) complexes

Gallati, Caroline Marie; Goetzfried, Sina Katharina; Ausserer, Marjana; Sagasser, Jessica; Plangger, Matthias; Wurst, Klaus; Hermann, Martin; Baecker, Daniel; Kircher, Brigitte; Gust, Ronald

doi:10.1039/c9dt04824c

Cited by 15 publications

(46 citation statements)

References 55 publications

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“…S1-S6, ESI †) did not differ from those of the mono-NHC gold(I) complexes. 45 However, in the 13 C NMR spectra, the signal of the C2 atom changed upon coordination of a second NHC from about 176 ppm ((NHC)Au I Br) to approximately 183 ppm (Fig. S7-S12, ESI †), indicating the formation of bis-NHC gold(I) compounds.…”

Section: Chemistrymentioning

confidence: 99%

“…The formation of the ligands 1a-f followed the same multistep procedure as that published previously. 45 Two synthesis routes were applied to obtain the bis-NHC gold(I) complexes 2a-f (Scheme 1). The first one (Method A) followed the synthesis of (NHC)Au I X complexes, but using a 2-fold excess of the ligand.…”

Section: Chemistrymentioning

confidence: 99%

“…The distance between the respective carbene carbons and the gold(I) centre amounts to 2.03 Å, very similar to that of the related mono-NHC gold(I) complexes (e.g., 3f: 2.00 Å). 45…”

Section: Chemistrymentioning

confidence: 99%

“…As it has already been reported, the ligands displayed scarcely any anti-proliferative activity. 45 Auranofin and/or Cisplatin were used in each experiment as references. Both compounds diminished the proliferation of A2780 cells at 1 µM to about 4%, but reduced the growth of A2780cis cells only to 50-60% (Fig.…”

Section: Determination Of Anti-proliferative Effectsmentioning

confidence: 99%

“…The compounds inhibited the growth and proliferation of A2780/ A2780cis and HL-60 cells in the micromolar range. 45 However, in aqueous solutions a ligand scrambling reaction to the related [(NHC) 2 Au I ] + species was noticed. 46 Because these degradation products might participate in the biological activity of (NHC)-Au I Br complexes, we synthesized a series of bis [3-ethyl-4-…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization and biological activity of bis[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes

et al. 2021

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

“…The distance between the respective carbene carbons and the gold(I) centre amounts to 2.03 Å, very similar to that of the related mono-NHC gold(I) complexes (e.g., 3f: 2.00 Å). 45…”

Section: Chemistrymentioning

confidence: 99%

Section: Determination Of Anti-proliferative Effectsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization and biological activity of bis[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes

et al. 2021

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Synthetic Strategies for the Preparation of Gold‐based Anticancer Agents

Gukathasan

Awuah

2022

Encyclopedia of Inorganic and Bioinorganic Chemistry

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Gold (Au) complexes attained an exceptional reach as new metal‐based anticancer agents in recent years. The FDA‐approved Au I complex auranofin [(2,3,4,6‐tetra‐ O ‐acetyl‐1‐thio‐β‐ d ‐glucopyranose (triethylphosphoranylidene)gold(I)] displays efficacious chemotherapeutic potential in phase I and II clinical trials for both liquid and solid tumors. Ignited by the success of auranofin as an anticancer agent, new designs and synthetic processes toward Au I and Au III complexes for unique biomedical applications are actively ongoing. In the past few years, Au III complexes have become attractive as premised on promising antitumor preclinical studies despite bottlenecks associated with stability and biological target identification. Advancement of gold complexes to the clinic will require agents with improved anticancer potency, unambiguous biological target, pharmacokinetic profile, and optimal stability. Thus, ligand tuning and innovative synthetic chemistry coupled with rigorous biological characterization are crucial. In this article, an overview of known synthetic strategies for the synthesis of gold anticancer complexes is presented. Primary focus on the synthesis of Au I and Au III complexes along with anticancer outcomes is outlined. This article presents medicinal inorganic chemists with an armory of synthetic tools and purification protocols to readily access highly potent gold anticancer agents.

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Gold Complexes in Anticancer Therapy: From New Design Principles to Particle‐Based Delivery Systems

2023

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The discovery of the medicinal properties of gold complexes has fuelled the design and synthesis of new anticancer metallodrugs, which have received special attention due to their unique modes of action. Current research in the development of gold compounds with therapeutic properties is predominantly focused on the molecular design of drug leads with superior pharmacological activities, e.g., by introducing targeting features. Moreover, intensive research aims at improving the physicochemical properties of gold compounds, such as chemical stability and solubility in the physiological environment. In this regard, the encapsulation of gold compounds in nanocarriers or their chemical grafting onto targeted delivery vectors could lead to new nanomedicines that eventually reach clinical applications. Herein, we provide an overview of the state‐of‐the‐art progress of gold anticancer compounds, andmore importantly we thoroughly revise the development of nanoparticle‐based delivery systems for gold chemotherapeutics.

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Synthesis, characterization and biological activity of bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes

Abstract: Bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes (8a–h) with methoxy, methyl and fluorine substituents at different positions in the 4-aryl ring were synthesized and characterized.

Cited by 15 publications

References 55 publications

Synthesis, characterization and biological activity of bis[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes

Synthesis, characterization and biological activity of bis[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes

Synthetic Strategies for the Preparation of Gold‐based Anticancer Agents

Gold Complexes in Anticancer Therapy: From New Design Principles to Particle‐Based Delivery Systems

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