New vanadium complexes with 6,6″-dimethyl-2,2′:6′,2″-terpyridine in terms of structure and biological properties

Fik, Marta A.; Gorczyński, Adam; Kubicki, Maciej; Hnatejko, Zbigniew; Wadas, Anna; Kulesza, Paweł J.; Lewińska, Agnieszka; Giel-Pietraszuk, Małgorzata; Wyszko, Eliza; Patroniak, Violetta

doi:10.1016/j.poly.2015.05.021

Cited by 20 publications

(8 citation statements)

References 63 publications

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“…This shows that the benzimidazole moiety effectively precludes the remaining species from intercalation or any other significant interaction with nucleic acids and the imidazole substituent can be used for tuning of the interaction strength. In our previous works [38,40,65], a similar phenomenon was observed, where complexes without hydrogen bonding donors in the “primary” structure bind to DNA scaffold—such as helical and “open” complexes with terpyridine-type and quaterpyridine-type ligands [66].…”

Section: Discussionsupporting

confidence: 67%

New Artificial Biomimetic Enzyme Analogues Based on Iron(II/III) Schiff Base Complexes: An Effect of (Benz)imidazole Organic Moieties on Phenoxazinone Synthase and DNA Recognition ‡

et al. 2019

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Elucidation of the structure and function of biomolecules provides us knowledge that can be transferred into the generation of new materials and eventually applications in e.g., catalysis or bioassays. The main problems, however, concern the complexity of the natural systems and their limited availability, which necessitates utilization of simple biomimetic analogues that are, to a certain degree, similar in terms of structure and thus behaviour. We have, therefore, devised a small library of six tridentate N-heterocyclic coordinating agents (L1–L6), which, upon complexation, form two groups of artificial, monometallic non-heme iron species. Utilization of iron(III) chloride leads to the formation of the 1:1 (Fe:Ln) ‘open’ complexes, whereas iron(II) trifluoromethanosulfonate allows for the synthesis of 1:2 (M:Ln) ‘closed’ systems. The structural differences between the individual complexes are a result of the information encoded within the metallic centre and the chosen counterion, whereas the organic scaffold influences the observed properties. Indeed, the number and nature of the external hydrogen bond donors coming from the presence of (benz)imidazole moieties in the ligand framework are responsible for the observed biological behaviour in terms of mimicking phenoxazinone synthase activity and interaction with DNA.

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Section: Discussionsupporting

confidence: 67%

New Artificial Biomimetic Enzyme Analogues Based on Iron(II/III) Schiff Base Complexes: An Effect of (Benz)imidazole Organic Moieties on Phenoxazinone Synthase and DNA Recognition ‡

et al. 2019

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“…The structures and activity of cell-cycle-disrupting vanadium compounds are summarized in Table 3. Some studies, described in the previous subsection, have found a connection between DNA binding and cell cycle arrest [27,28,31,40] (Table 1) as well as oxidative stress and cell cycle progression [49,52,55] (Table 2). Wu et al [49] have demonstrated that the ROS-induced sustained MAPK/ERK activation contributed to vanadium-compound-induced G2/M cell cycle arrest in pancreatic cancer cells.…”

Section: Cell Cycle Arrestmentioning

confidence: 94%

“…Interestingly, a non-oxido vanadium(IV) complex with a catechol-modified 3,3 -diindolylmethane (4) exhibited stronger DNA binding than cisplatin [27]. Importantly, Fik et al [28] have demonstrated that vanadium complexes with dimethylterpyridine (5 and 6) exhibited cytotoxic activity against human cervical carcinoma cells by direct interactions with DNA, thus increasing the level of arrest cells in stage G2/M. The DNA interaction ability has been determined also for the phenantroline vanadium complex (7-10) with simultaneous cytotoxic activity against human ovarian and breast carcinoma cells [29].…”

Section: Dna: the Classical Targetmentioning

confidence: 99%

Molecular and Cellular Mechanisms of Cytotoxic Activity of Vanadium Compounds against Cancer Cells

2020

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Discovering that metals are essential for the structure and function of biomolecules has given a completely new perspective on the role of metal ions in living organisms. Nowadays, the design and synthesis of new metal-based compounds, as well as metal ion binding components, for the treatment of human diseases is one of the main aims of bioinorganic chemistry. One of the areas in vanadium-based compound research is their potential anticancer activity. In this review, we summarize recent molecular and cellular mechanisms in the cytotoxic activity of many different synthetic vanadium complexes as well as inorganic salts. Such mechanisms shall include DNA binding, oxidative stress, cell cycle regulation and programed cell death. We focus mainly on cellular studies involving many type of cancer cell lines trying to highlight some new significant advances.

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“…In the literature, there are described terpyridine complexes containing platinum, ruthenium, vanadium, palladium, copper, iron, and others metals, which exhibit biological activity. What is worth to emphasizing, the knowledge about the activity of free ligands based on terpyridine structure is relatively unknown…”

Section: Introductionmentioning

confidence: 99%

4′‐Phenyl‐2,2′:6′,2′′‐terpyridine Derivatives Containing 1‐Substituted‐2,3‐Triazole Ring: Synthesis, Characterization and Anticancer Activity

et al. 2018

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Terpyridine moiety is known for chelating and interesting physicochemical properties enabling some applications. Its biological activity, particularly anticancer potency is not well studied. Herein we present six 4′‐(1‐substituted‐2,3‐triazol‐4‐yl)phenyl‐2,2′:6′,2′′‐terpyridine derivatives with glycidyl, cyclohexylmethyl, benzyl, 4‐tert‐butylbenzyl, pentafluorobenzyl, and 2,6‐dichlorobenzyl groups which were obtained via Cu(I)‐catalysed 1,3‐dipolar cycloaddition reaction. The photophysical such as optical (absorption and photoluminescence spectra, quantum yields and lifetimes) and thermal (by using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA)) properties were examined. In addition, theoretical studies (DFT and TD‐DFT) were performed to provide a deeper understanding of the experimental results. In vitro studies on the obtained novel structures were conducted with selected series of cell lines to check their bioactivity and toxicity. The most active compound reached a nanomolar level with good selectivity index better than doxorubicin. Mechanism of action for these terpyridines was also investigated which suggest intercalation of DNA as a trigger of cell death.

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New vanadium complexes with 6,6″-dimethyl-2,2′:6′,2″-terpyridine in terms of structure and biological properties

Cited by 20 publications

References 63 publications

New Artificial Biomimetic Enzyme Analogues Based on Iron(II/III) Schiff Base Complexes: An Effect of (Benz)imidazole Organic Moieties on Phenoxazinone Synthase and DNA Recognition ‡

New Artificial Biomimetic Enzyme Analogues Based on Iron(II/III) Schiff Base Complexes: An Effect of (Benz)imidazole Organic Moieties on Phenoxazinone Synthase and DNA Recognition ‡

Molecular and Cellular Mechanisms of Cytotoxic Activity of Vanadium Compounds against Cancer Cells

4′‐Phenyl‐2,2′:6′,2′′‐terpyridine Derivatives Containing 1‐Substituted‐2,3‐Triazole Ring: Synthesis, Characterization and Anticancer Activity

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