Synthesis, characterization and albumin binding capabilities of quinizarin containing ternary cobalt(III) complexes

Kozsup, Máté; Dömötör, Orsolya; Nagy, Sándor; Farkas, Etelka; Enyedy, Éva A.; Buglyó, Péter

doi:10.1016/j.jinorgbio.2019.110963

Cited by 13 publications

(7 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…After one day had passed, the phases were separated, centrifuged, and the absorption of the solution was measured again. From the absorption difference of the stock solutions, the distribution coefficient (D) was determined using previously described formulae [ 71 ].…”

Section: Methodsmentioning

confidence: 99%

Reactive Oxygen Species Production Is Responsible for Antineoplastic Activity of Osmium, Ruthenium, Iridium and Rhodium Half-Sandwich Type Complexes with Bidentate Glycosyl Heterocyclic Ligands in Various Cancer Cell Models

Kacsir

Sipos

Bényei

et al. 2022

IJMS

Self Cite

View full text Add to dashboard Cite

Platinum complexes are used in chemotherapy, primarily as antineoplastic agents. In this study, we assessed the cytotoxic and cytostatic properties of a set of osmium(II), ruthenium(II), iridium(III) and rhodium(III) half-sandwich-type complexes with bidentate monosaccharide ligands. We identified 5 compounds with moderate to negligible acute cytotoxicity but with potent long-term cytostatic activity. These structure-activity relationship studies revealed that: 1) osmium(II) p-cymene complexes were active in all models, while rhodium(III) and iridium(III) Cp* complexes proved largely inactive; 2) the biological effect was influenced by the nature of the central azole ring of the ligands—1,2,3-triazole was the most effective, followed by 1,3,4-oxadiazole, while the isomeric 1,2,4-oxadiazole abolished the cytostatic activity; 3) we found a correlation between the hydrophobic character of the complexes and their cytostatic activity: compounds with O-benzoyl protective groups on the carbohydrate moiety were active, compared to O-deprotected ones. The best compound, an osmium(II) complex, had an IC50 value of 0.70 µM. Furthermore, the steepness of the inhibitory curve of the active complexes suggested cooperative binding; cooperative molecules were better inhibitors than non-cooperative ones. The cytostatic activity of the active complexes was abolished by a lipid-soluble antioxidant, vitamin E, suggesting that oxidative stress plays a major role in the biological activity of the complexes. The complexes were active on ovarian cancer, pancreatic adenocarcinoma, osteosarcoma and Hodgkin’s lymphoma cells, but were inactive on primary, non-transformed human fibroblasts, indicating their applicability as potential anticancer agents.

show abstract

Section: Methodsmentioning

confidence: 99%

Reactive Oxygen Species Production Is Responsible for Antineoplastic Activity of Osmium, Ruthenium, Iridium and Rhodium Half-Sandwich Type Complexes with Bidentate Glycosyl Heterocyclic Ligands in Various Cancer Cell Models

Kacsir

Sipos

Bényei

et al. 2022

IJMS

Self Cite

View full text Add to dashboard Cite

show abstract

“…After 1 day, the phases were separated and centrifuged, and the absorption of the solution was measured again. From the absorption difference of the stock solutions, the distribution coefficient (D) was calculated according to the previously described formulae [ 66 ].…”

Section: Methodsmentioning

confidence: 99%

Ruthenium Half-Sandwich Type Complexes with Bidentate Monosaccharide Ligands Show Antineoplastic Activity in Ovarian Cancer Cell Models through Reactive Oxygen Species Production

Kacsir

Sipos

Ujlaki

et al. 2021

IJMS

Self Cite

View full text Add to dashboard Cite

Ruthenium complexes are developed as substitutes for platinum complexes to be used in the chemotherapy of hematological and gynecological malignancies, such as ovarian cancer. We synthesized and screened 14 ruthenium half-sandwich complexes with bidentate monosaccharide ligands in ovarian cancer cell models. Four complexes were cytostatic, but not cytotoxic on A2780 and ID8 cells. The IC50 values were in the low micromolar range (the best being 0.87 µM) and were similar to or lower than those of the clinically available platinum complexes. The active complexes were cytostatic in cell models of glioblastoma, breast cancer, and pancreatic adenocarcinoma, while they were not cytostatic on non-transformed human skin fibroblasts. The bioactive ruthenium complexes showed cooperative binding to yet unidentified cellular target(s), and their activity was dependent on reactive oxygen species production. Large hydrophobic protective groups on the hydroxyl groups of the sugar moiety were needed for biological activity. The cytostatic activity of the ruthenium complexes was dependent on reactive species production. Rucaparib, a PARP inhibitor, potentiated the effects of ruthenium complexes.

show abstract

“…In recent years the interaction of hypericin, emodin, quinizarin, and danthron with biomacromolecules has been studied, especially with DNA, LDL, and human serum albumin (HSA) has been investigated [199][200][201][202]. The results of our studies in this area supplement the scientific knowledge on this subject.…”

Section: Hypericin and Its Derivatives Interaction With Dnamentioning

confidence: 62%

Biophysical Characterization and Anticancer Activities of Photosensitive Phytoanthraquinones Represented by Hypericin and Its Model Compounds

2020

View full text Add to dashboard Cite

Photosensitive compounds found in herbs have been reported in recent years as having a variety of interesting medicinal and biological activities. In this review, we focus on photosensitizers such as hypericin and its model compounds emodin, quinizarin, and danthron, which have antiviral, antifungal, antineoplastic, and antitumor effects. They can be utilized as potential agents in photodynamic therapy, especially in photodynamic therapy (PDT) for cancer. We aimed to give a comprehensive summary of the physical and chemical properties of these interesting molecules, emphasizing their mechanism of action in relation to their different interactions with biomacromolecules, specifically with DNA.

show abstract

Synthesis, characterization and albumin binding capabilities of quinizarin containing ternary cobalt(III) complexes

Cited by 13 publications

References 43 publications

Reactive Oxygen Species Production Is Responsible for Antineoplastic Activity of Osmium, Ruthenium, Iridium and Rhodium Half-Sandwich Type Complexes with Bidentate Glycosyl Heterocyclic Ligands in Various Cancer Cell Models

Reactive Oxygen Species Production Is Responsible for Antineoplastic Activity of Osmium, Ruthenium, Iridium and Rhodium Half-Sandwich Type Complexes with Bidentate Glycosyl Heterocyclic Ligands in Various Cancer Cell Models

Ruthenium Half-Sandwich Type Complexes with Bidentate Monosaccharide Ligands Show Antineoplastic Activity in Ovarian Cancer Cell Models through Reactive Oxygen Species Production

Biophysical Characterization and Anticancer Activities of Photosensitive Phytoanthraquinones Represented by Hypericin and Its Model Compounds

Contact Info

Product

Resources

About