Synthesis, structural analysis, redox properties and in vitro antitumor evaluation of half-sandwich complexes of Ru(II) with aminocoumarins

Skoczyńska, Anna; Małecka, Magdalena; Cieślak, Marcin; Kaźmierczak-Barańska, Julia; Królewska-Golińska, Karolina; Leniart, Andrzej; Budzisz, Elżbieta

doi:10.1016/j.poly.2017.02.011

Cited by 18 publications

(9 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All these complexes were fully characterized by IR, NMR, elemental analysis, and mass spectrometry. The 1 H-NMR spectra of the complexes showed resonances that agree with previously reported analogues [ 31 , 32 ]. All of the complexes exhibited a doublet at 0.76–0.86 ppm, which is assigned to the two methyl groups of the isopropyl substituent of the arene ligands, and singlet peaks at 1.83–1.90 ppm, which correspond to the three protons of the methyl in the p -cymene.…”

Section: Resultssupporting

confidence: 88%

DNA-Binding Capabilities and Anticancer Activities of Ruthenium(II) Cymene Complexes with (Poly)cyclic Aromatic Diamine Ligands

et al. 2020

View full text Add to dashboard Cite

Ruthenium(II) arene complexes of the general formula [RuCl(η6-p-cymene)(diamine)]PF6 (diamine = 1,2-diaminobenzene (1), 2,3-diaminonaphthalene (2), 9,10-diaminophenanthrene (3), 2,3-diaminophenazine (4), and 1,2-diaminoanthraquinone (5) were synthesized. Chloro/aqua exchange was evaluated experimentally for complexes 1 and 2. The exchange process was investigated theoretically for all complexes, revealing relatively fast exchange with no significant influence from the polycyclic aromatic diamines. The calf thymus DNA (CT-DNA) binding of the complexes increased dramatically upon extending the aromatic component of the diamines, as evaluated by changes in absorption spectra upon titration with different concentrations of CT-DNA. An intercalation binding mode was established for the complexes using the increase in the relative viscosity of the CT-DNA following addition of complexes 1 and 2. Theoretical studies showed strong preference for replacement of water by guanine for all the complexes, and relatively strong Ru–Nguanine bonds. The plane of the aromatic systems can assume angles that support non-classical interactions with the DNA and covalent binding, leading to higher binding affinities. The ruthenium arenes illustrated in this study have promising anticancer activities, with the half maximal inhibitory concentration (IC50) values comparable to or better than cisplatin against three cell lines.

show abstract

Section: Resultssupporting

confidence: 88%

DNA-Binding Capabilities and Anticancer Activities of Ruthenium(II) Cymene Complexes with (Poly)cyclic Aromatic Diamine Ligands

et al. 2020

View full text Add to dashboard Cite

show abstract

“…[34,35] Additionally, compounds presenting a coumarin scaffold display broad pharmacological activities and their potential as anticancer agents has received a lot of interest. [36][37][38][39][40] In the particular case of traceable organometallic drugs, two strategies can be considered: 1) direct coordination of the (coumarin) fluorophore to the metal center [41,42] or 2) anchoring of the dye to more elaborated ligands. [32,43,44] The nature of the metal center as well as the type of the ligand can strongly affect the photophysical properties of the hybrid molecule.…”

Section: Introductionmentioning

confidence: 99%

“…In the particular case of traceable organometallic drugs, two strategies can be considered: 1) direct coordination of the (coumarin) fluorophore to the metal center or 2) anchoring of the dye to more elaborated ligands. [32,43, 44] The nature of the metal center as well as the type of the ligand can strongly affect the photophysical properties of the hybrid molecule.…”

Section: Introductionmentioning

confidence: 99%

Coumarin‐Tagged Dinuclear Trithiolato‐Bridged Ruthenium(II)⋅Arene Complexes: Photophysical Properties and Antiparasitic Activity

et al. 2020

View full text Add to dashboard Cite

The synthesis, characterization, photophysical and biological properties of 13 new conjugate coumarin-diruthenium(II)•arene complexes against Toxoplasma gondii are presented. For all conjugate organometallic unit/coumarins, an almost complete loss of fluorescence efficacy was observed. However, the nature of the fluorophore, the type of bonding, the presence and length of a linker between the coumarin dye and the ruthenium(II) moiety, and the number of dye units influenced their biological properties. The in vitro activity against a trans-genic T. gondii strain grown in human foreskin fibroblasts (HFF) leads to IC 50 values for T. gondii β-gal from 105 to 735 nM. Of note is that nine compounds displayed lower IC 50 than the standard drug pyrimethamine. One compound applied at its IC 50 did not affect B-cell proliferation but had an impact on Tcell proliferation in murine splenocyte cultures. Transmission electron microscopy of T. gondii β-gal-infected HFF showed that treatment predominantly affected the parasites' mitochondrion.

show abstract

“…Previously reported articles have also shown that with the increase in the electron‐donating ability of the substituents, the biological activity of the compound also increases. [ 36 ] The cytotoxicity studies of some of the reported ruthenium complexes bearing coumarin derivative [ 37 ] when compared with our compounds shows that they are good anticancer agents (complexes 5 and 6 ) where their activity is almost comparable with that of cisplatin.…”

Section: Resultsmentioning

confidence: 87%

Ruthenium, rhodium, and iridium complexes featuring coumarin hydrazone derivatives: Synthesis, characterization, and preliminary investigation of their anticancer and antibacterial activity

Dkhar

Verma

Banothu

et al. 2022

Applied Organom Chemis

View full text Add to dashboard Cite

Coumarin hydrazone derivatives (L1, L2, L3, and L4) have been prepared by Knoevenagel condensation. Half‐sandwich ruthenium, rhodium, and iridium complexes containing these coumarin hydrazone derivatives (1–12) have been synthesized. The deprotonation of hydrazinic proton from the ligand leads to the formation of anionic species, thereby forming neutral N ∩ N chelation complexes. These complexes have been confirmed by spectroscopic technique and single‐crystal X‐ray diffraction studies. Spectroscopic analysis of the ligands and complexes shows that the data are consistent with the formulated data. The stability studies of some of the complexes (1, 5, and 6) were performed by the 1H‐NMR technique using deuterated DMSO‐d6 solvent. They are found to be stable in solution as well as in the air and are nonhygroscopic. In vitro antibacterial activity against gram‐positive Staphylococcus aureus and gram‐negative Escherichia coli, Klebsiella pneumoniae strains have been tested. Also, their cytotoxicity study was evaluated against Dalton's ascites lymphoma (DL), Ehrlich ascites carcinoma (EAC), and normal cell lines (peripheral blood mononuclear cells [PBMC]). In both the studies, complexes (5 and 6) are found to be the most active compared to the other complexes.

show abstract

Synthesis, structural analysis, redox properties and in vitro antitumor evaluation of half-sandwich complexes of Ru(II) with aminocoumarins

Cited by 18 publications

References 55 publications

DNA-Binding Capabilities and Anticancer Activities of Ruthenium(II) Cymene Complexes with (Poly)cyclic Aromatic Diamine Ligands

DNA-Binding Capabilities and Anticancer Activities of Ruthenium(II) Cymene Complexes with (Poly)cyclic Aromatic Diamine Ligands

Coumarin‐Tagged Dinuclear Trithiolato‐Bridged Ruthenium(II)⋅Arene Complexes: Photophysical Properties and Antiparasitic Activity

Ruthenium, rhodium, and iridium complexes featuring coumarin hydrazone derivatives: Synthesis, characterization, and preliminary investigation of their anticancer and antibacterial activity

Contact Info

Product

Resources

About