Synthesis, structure and antiproliferative activity of dinuclear ruthenium arene complexes with differently coordinated thiosemicarbazones

Su, Wei; Li, Yuchun; Xiao, Jun‐An; Zhang, Yuexing; Li, Peiyuan

doi:10.1002/aoc.4420

Cited by 5 publications

(2 citation statements)

References 36 publications

(57 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In this way, the creation of a synergistic effect between the ligand and the metal center may increase the biological activity of the complex. TSCs have been of interest due to their different biological properties ( Su et al, 2018 ). Moreover, TSCs are in the class of N , S chelating ligands, therefore metals can be coordinated with TSC ligands.…”

Section: Introductionmentioning

confidence: 99%

Half-Sandwich Arene Ruthenium(II) Thiosemicarbazone Complexes: Evaluation of Anticancer Effect on Primary and Metastatic Ovarian Cancer Cell Lines

et al. 2022

View full text Add to dashboard Cite

In this study, we describe the synthesis, characterization and antiproliferative activity of three organo-ruthenium(II) half-sandwich complexes [RuCl(η6-p-cym)(N,S-L)]Cl (I, II, and III). To form these complexes, three thiosemicarbazone ligands (TSCs) were synthesized; L = 5-nitro-2-carboxyaldehyde-thiophen-N-methyl-thiosemicarbazone, (L1); 2-acetyl-5-bromo-thiophen-N-methyl-thiosemicarbazone, (L2) and 2-acetyl-5-bromo-thiophen-N,N-dimethyl-thiosemicarbazone, (L3). The isolated compounds were analyzed using spectroscopic techniques such as elemental analysis, conductance measurements, FT-IR, 1H NMR spectroscopy, MALDI-TOF mass spectrometry, and single-crystal XRD. Our results demonstrated that the synthesized thiosemicarbazone ligands (TSCs) are bound to the metal ion as a bidentate ligand that coordinates through the thiocarbonyl sulfur and azomethine nitrogen atoms in all complexes (I, II, and III). The X-ray crystal structures of L1 and L2 revealed that both compounds are crystallized in the triclinic crystal system with space group P-1. The biological potency of newly synthesized TSC ligands (L1, L2, and L3) and their corresponding ruthenium complexes (I, II, and III) were investigated on human primary ovarian (A2780) and human metastatic ovarian (OVCAR-3) cell lines. To get detailed information respecting antitumor properties, cytotoxicity, DNA/BSA binding affinity, cellular uptake, DNA binding competition, and trans-epithelial resistance measurement assays were performed. Our results demonstrate that newly synthesized ruthenium(II) complexes possess potential biological activity. Moreover, we observe that the ruthenium complexes reported here show anticancer activity on primary (A2780) and metastatic (OVCAR-3) ovarian cancer cells.

show abstract

Section: Introductionmentioning

confidence: 99%

Half-Sandwich Arene Ruthenium(II) Thiosemicarbazone Complexes: Evaluation of Anticancer Effect on Primary and Metastatic Ovarian Cancer Cell Lines

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Meanwhile, Ru(II)–arene complexes are widely used as catalysts due to their ease of preparation, 5 unique reactivity and selectivity, such as in arylation reactions, 6 catalytic reduction of esters, 7 catalytic oxidation of alcohols 8 and carbon–hydrogen bond functionalization 9 . As cost‐effective precursors, Ru(II)–arene complexes have attracted great interest in the fields of biology and materials science 10–12 . Recently, Ru(II) metallized [1 5 ]paracyclophanes (Ru‐[1 5 ]PCPs) have been successfully used as anion receptors to bind oxo‐anions through coordinated benzene rings, and have shown extensive host–guest interactions in solution 13,14 …”

Section: Introductionmentioning

confidence: 99%

Investigating the exceptional adducts of alkoxides with Ru(II)–arene cations in alkyl alcohol solution using electrospray ionization mass spectrometry

Cao

Dong

et al. 2021

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Rationale Exploring the formation mechanism of the exceptional adducts of alkoxides with Ru(II)–arene cations in alkyl alcohol solution using electrospray ionization mass spectrometry (ESI‐MS) is crucial for further understanding the physicochemical properties of Ru(II)–arene complexes in solution. Methods All mass spectra were collected with an AB SCIEX TripleTOF 5600+ mass spectrometer in positive mode. Theoretical calculations were carried out using the density functional theory method at the B3LYP level with a hybrid basis set consisting of 6‐31G(d,p) and LanL2DZ in the Gaussian 03 program. Results When ruthenated [15]paracyclophanes (Ru‐[15]PCPs) and Ru(II)–arene dimers were dissolved in alkyl alcohol solvents, the adducts of alkoxides with Ru(II)–arene cations were observed under positive ion mode ESI‐MS, which resulted from the coordination of alkyl alcohol molecules with the Ru(II)–arene cations followed by the deprotonation of O‐H bonds of the coordinated alcohols. Furthermore, the number of alkoxides binding to Ru‐[15]PCPs was regulated by the number of ruthenium atoms. Attributed to good solubility and small steric hindrance, the signal intensity of the adducts of methoxides with Ru(II)–arene cations was the strongest among the three alkyl alcohols used in this study. Conclusions The characteristic adducts of alkoxides with Ru(II)–arene cations were pervasively present in positive ion mode ESI‐MS of nine Ru(II)–arene complexes dissolved in alkyl alcohol solvents. Taking into consideration the solubility and signal response, methanol is the most suitable solvent for the ESI‐MS experiments with Ru(II)–arene complexes among the solvents studied, where almost only the diagnostic adducts of methoxides with Ru(II)–arene cations are present.

show abstract

New solvatochromic complexes of 1,2‐bis[(5,6‐diphenyl‐1,2,4‐triazin3‐yl)hydrazinylidene‐methyl]benzene: Synthesis, spectroscopic, biological, docking, and theoretical studies

Samy

Taha

Omar

2021

Applied Organom Chemis

View full text Add to dashboard Cite

A new bistriazine hydrazone ligand (H2L; H2BDTB) is derived from 5,6‐diphenyl‐1,2,4‐triazine‐3‐ylhydrazine (DTH) with o‐phthalaldehyde in ratio (2:1). The Fe(III), Co(II), Ni(II), Cu(II), and Th(IV) complexes (1–5), as well as the Co(II) complex (6) (prepared in the presence of cetyltrimethylammonium bromide [CTAB]), are synthesized. They are characterized by elemental analyses, spectral (ultraviolet–visible [UV–Vis], infrared [IR], mass, 1H NMR, and electron spin resonance [ESR]), magnetic susceptibility, molar conductivity, and thermal gravimetric analysis (TGA) measurements; and morphological structures are scanned by electron microscopy (SEM) that showed rod shape, irregular bulk sheets, and fused aggregated clusters for free ligand, Co(II) complexes (2 and 6), respectively. Moreover, cobalt(II) complex (6) exhibited an octahedral geometry; however, cobalt(II) complex (2) showed square planar geometry as deduced from magnetic moment and UV–Vis measurements. Fluorescence spectra for ligand and its Fe(III) and Th(IV) complexes have been measured in different solvents to investigate their solvatochromic behavior that used to estimate dipole moments either in ground and excited states. The antimicrobial and antitumor activities of free ligand and its complexes were investigated, in addition to molecular docking studies using MOE 2014.0901 software (PDB. I.D.3ce3). The data showed that Co(II) complex (6) can be nominated as one of the most powerful antitumor. The theoretical calculation for bistriazine ligand and its complexes were performed using DFT and PM3, and the data are correlated with the experimental results.

show abstract

Synthesis, structure and antiproliferative activity of dinuclear ruthenium arene complexes with differently coordinated thiosemicarbazones

Cited by 5 publications

References 36 publications

Half-Sandwich Arene Ruthenium(II) Thiosemicarbazone Complexes: Evaluation of Anticancer Effect on Primary and Metastatic Ovarian Cancer Cell Lines

Half-Sandwich Arene Ruthenium(II) Thiosemicarbazone Complexes: Evaluation of Anticancer Effect on Primary and Metastatic Ovarian Cancer Cell Lines

Investigating the exceptional adducts of alkoxides with Ru(II)–arene cations in alkyl alcohol solution using electrospray ionization mass spectrometry

New solvatochromic complexes of 1,2‐bis[(5,6‐diphenyl‐1,2,4‐triazin3‐yl)hydrazinylidene‐methyl]benzene: Synthesis, spectroscopic, biological, docking, and theoretical studies

Contact Info

Product

Resources

About