Crystal structures, DNA-binding ability and influence on cellular viability of gold(I) complexes of thiosemicarbazones

Almeida, Carolane M.; Nascimento, Gabriel P.; Magalhães, Kelly Grace; Iglesias, Bernardo A.; Gatto, Claudia C.

doi:10.1080/00958972.2018.1435869

Cited by 10 publications

(4 citation statements)

References 41 publications

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“…[26,28] Gold(I)-HTSC compounds that interact with DNA have been also studied by fluorescence measurements, however, K SV values have not been reported. [43] These results suggest that 2 has the ability to bind to DNA, similar to has been reported for other gold(I) compounds. [10,11] Table 3.…”

Section: Chempluschemsupporting

confidence: 80%

“…Several gold(I) compounds containing thiosemicarbazones (acting as neutral protonated ligands, HTSC) and displaying anticancer activities have been described (Figure 1). Compounds can be mono- [41][42][43][44][45] [AuL(HTSC)] or [AuL(HTSC)]X (X=Cl À or PF 6 À ) and bimetallic [43,46,47] [{Au(HTSC)} 2 ]X 2 (X=Cl À or I À ). In most cases an activity higher than that of the thiosemicarbazone ligands is described, and for most of the compounds reported this activity seems to correlate to thioredoxin reductase (TrRx) inhibition, or the ability of the gold compounds to bind to DNA.…”

Section: Introductionmentioning

confidence: 99%

“…Chemical structures of Auranofin (AF) and reported mono-and bimetallic god(I) compounds with anticancer activity. [36][37][38][39][40][41][42][43] ChemPlusChem bio reduced by parasite's enzymes to a nitro anion radical (NO 2…”

Section: Introductionmentioning

confidence: 99%

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5‐Nitrofuryl‐Containing Thiosemicarbazone Gold(I) Compounds: Synthesis, Stability Studies, and Anticancer Activity

Rodríguez‐Arce,

Gavrilov,

Alvite

et al. 2023

ChemPlusChem

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This work describes the synthesis of four gold(I) [AuClL] compounds containing chloro and biologically active protonated thiosemicarbazones based on 5‐nitrofuryl (L=HSTC). The stability of the compounds in dichloromethane, DMSO, and DMSO/culture media solutions was investigated by spectroscopy, cyclic voltammetry, and conductimetry, indicating the formation overtime of cationic monometallic [Au(HTSC)(DMSO)]± or [Au(HTSC)2]±, and/or dimeric species. Neutral [{Au(TSC)}2] species were obtained from one of the compounds in dichlomethane/n‐hexane solution and characterized by X‐ray crystallography revealing a Au−Au bond, and deprotonated thiosemicarbazone (TSC). The cytotoxicity of the gold compounds and thiosemicarbazone ligands was evaluated against selected cancer cell lines and compared to that of Auranofin. Studies of the most stable, cytotoxic, and selective compound on a renal cancer cell line (Caki‐1) demonstrated its relevant antimigratory and anti‐angiogenic properties, and preferential accumulation in the cell nuclei. Its mode of action seems to involve interaction with DNA, and subsequent cell death via apoptosis.

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Section: Chempluschemsupporting

confidence: 80%

Section: Introductionmentioning

confidence: 99%

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5‐Nitrofuryl‐Containing Thiosemicarbazone Gold(I) Compounds: Synthesis, Stability Studies, and Anticancer Activity

Rodríguez‐Arce,

Gavrilov,

Alvite

et al. 2023

ChemPlusChem

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“…Emission fluorescence shows a decrease in emission intensity and displacement of the ethidium/DNA adduct after the addition of the gold(I) complex. This is due to competition between the gold(I) derivative and ethidium bromide for binding to the DNA groove …”

Section: Mechanism Of Actionmentioning

confidence: 99%

Next Generation Gold Drugs and Probes: Chemistry and Biomedical Applications

et al. 2023

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The gold drugs, gold sodium thiomalate (Myocrisin), aurothioglucose (Solganal), and the orally administered auranofin (Ridaura), are utilized in modern medicine for the treatment of inflammatory arthritis including rheumatoid and juvenile arthritis; however, new gold agents have been slow to enter the clinic. Repurposing of auranofin in different disease indications such as cancer, parasitic, and microbial infections in the clinic has provided impetus for the development of new gold complexes for biomedical applications based on unique mechanistic insights differentiated from auranofin. Various chemical methods for the preparation of physiologically stable gold complexes and associated mechanisms have been explored in biomedicine such as therapeutics or chemical probes. In this Review, we discuss the chemistry of next generation gold drugs, which encompasses oxidation states, geometry, ligands, coordination, and organometallic compounds for infectious diseases, cancer, inflammation, and as tools for chemical biology via gold–protein interactions. We will focus on the development of gold agents in biomedicine within the past decade. The Review provides readers with an accessible overview of the utility, development, and mechanism of action of gold-based small molecules to establish context and basis for the thriving resurgence of gold in medicine.

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Organometallic gold (III) and platinum (II) complexes with thiosemicarbazone: Structural behavior, anticancer activity, and molecular docking

Almeida

Marcon

Nascimento

et al. 2022

Applied Organom Chemis

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This study reports the synthesis and characterization of two new organometallic Au (III) and Pt (II) complexes with 2‐acetylthiophene‐N(3)‐methylthiosemicarbazone (HL). The characterization of the compounds was performed by single‐crystal X‐ray diffraction and spectroscopic techniques (Fourier transform infrared (FT‐IR), UV–Vis, electrospray ionization (ESI)(+)‐mass spectrometry (MS), and nuclear magnetic resonance (NMR)). The MS data indicated the presence in the solution of the molecular ion [H2L]+ and characteristic fragmentations of the ligand. The thiosemicarbazone is coordinated to the Au (III) and Pt (II) in tridentate mode through the CNS chelating system. The two metal atoms show a distorted square geometry including chloride ion or triphenylphosphine to complete the coordination sphere. The 3D Hirshfeld surface and the 2D fingerprint results were analyzed quantitatively to verify interactions upon the molecular packing. The biological activity of the free thiosemicarbazone and their complexes have been evaluated against the MCF‐7 human cancer cell line. Molecular docking was used to predict the inhibitory activity of the compounds.

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Crystal structures, DNA-binding ability and influence on cellular viability of gold(I) complexes of thiosemicarbazones

Cited by 10 publications

References 41 publications

5‐Nitrofuryl‐Containing Thiosemicarbazone Gold(I) Compounds: Synthesis, Stability Studies, and Anticancer Activity

5‐Nitrofuryl‐Containing Thiosemicarbazone Gold(I) Compounds: Synthesis, Stability Studies, and Anticancer Activity

Next Generation Gold Drugs and Probes: Chemistry and Biomedical Applications

Organometallic gold (III) and platinum (II) complexes with thiosemicarbazone: Structural behavior, anticancer activity, and molecular docking

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