Ruthenium(II) trithiacyclononane complexes of 7,3′,4′-trihydroxyflavone, chrysin and tectochrysin: Synthesis, characterisation, and cytotoxic evaluation

Marques, Joana; Silva, Artur M. S.; Marques, M. P. M.; Braga, Susana S.

doi:10.1016/j.ica.2019.01.003

Cited by 15 publications

(11 citation statements)

References 56 publications

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“…Other studies have shown that baicalein can mitigate cell proliferation and diminish the production of collagen; also, it possesses multiple effective properties for the treatment of different diseases including cancer and injuries [36][37][38][39]. Lastly, 7,4'-dihydroxyflavone, also named 5-deoxyluteolin, has shown impressive antimycobacterial activity and its anti-inflammatory activity is under evaluation [40]. The comparison of C1 versus C2 leaves showed an increase in anthocyanins and flavones, although with moderate FC values.…”

Section: Uhplc-qtof Mass Spectrometry Untargeted Profiling and Effectmentioning

confidence: 99%

Hydroponically Grown Sanguisorba minor Scop.: Effects of Cut and Storage on Fresh-Cut Produce

et al. 2019

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Wild edible plants have been used in cooking since ancient times. Recently, their value has improved as a result of the scientific evidence for their nutraceutical properties. Sanguisorba minor Scop. (salad burnet) plants were hydroponically grown and two consecutive cuts took place at 15 (C1) and 30 (C2) days after sowing. An untargeted metabolomics approach was utilized to fingerprint phenolics and other health-related compounds in this species; this approach revealed the different effects of the two cuts on the plant. S. minor showed a different and complex secondary metabolite profile, which was influenced by the cut. In fact, flavonoids increased in leaves obtained from C2, especially flavones. However, other secondary metabolites were downregulated in leaves from C2 compared to those detected in leaves from C1, as evidenced by the combination of the variable important in projections (VIP score > 1.3) and the fold-change (FC > 2). The storage of S. minor leaves for 15 days as fresh-cut products did not induce significant changes in the phenolic content and antioxidant capacity, which indicates that the nutraceutical value was maintained. The only difference evidenced during storage was that leaves obtained from C2 showed a lower constitutive content of nutraceutical compounds than leaves obtained from C1; except for chlorophylls and carotenoids. In conclusion, the cut was the main influence on the modulation of secondary metabolites in leaves, and the effects were independent of storage.

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Section: Uhplc-qtof Mass Spectrometry Untargeted Profiling and Effectmentioning

confidence: 99%

Hydroponically Grown Sanguisorba minor Scop.: Effects of Cut and Storage on Fresh-Cut Produce

et al. 2019

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“…Amidst flavonoids, quercetin and its metal complexes have been studied in terms of DNA binding studies, in order to establish structure-activity relationships [58]. Recently, Ru [59][60][61][62][63][64][65][66], V [67,68], Zn [69], Cu [70,71], Fe [72] and La [73] complexes bearing bioactive flavonoids or related ligands have been described. This also include half-sandwich ruthenium [74][75][76][77], rhodium [74,75] and osmium [75,78] derivatives that exhibit cytotoxic activity.…”

Section: Introductionmentioning

confidence: 99%

Anticancer Activity of Half-Sandwich Ru, Rh and Ir Complexes with Chrysin Derived Ligands: Strong Effect of the Side Chain in the Ligand and Influence of the Metal

et al. 2021

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An important challenge in the field of anticancer chemotherapy is the search for new species to overcome the resistance of standard drugs. An interesting approach is to link bioactive ligands to metal fragments. In this work, we have synthesized a set of p-cymene-Ru or cyclopentadienyl-M (M = Rh, Ir) complexes with four chrysin-derived pro-ligands with different -OR substituents at position 7 of ring A. The introduction of a piperidine ring on chrysin led to the highly cytotoxic pro-ligand HL4 and its metal complexes L4-M (SW480 and A549 cell lines, cytotoxic order: L4-Ir > L4-Ru ≈ L4-Rh). HL4 and its complexes induce apoptosis and can overcome cis-platinum resistance. However, HL4 turns out to be more cytotoxic in healthy than in tumor cells in contrast to its metal complexes which displayed higher selectivity than cisplatin towards cancer cells. All L4-M complexes interact with double stranded DNA. Nonetheless, the influence of the metal is clear because only complex L4-Ir causes DNA cleavage, through the generation of highly reactive oxygen species (1O2). This result supports the hypothesis of a potential dual mechanism consisting of two different chemical pathways: DNA binding and ROS generation. This behavior provides this complex with a great effectivity in terms of cytotoxicity.

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“…In the case of ruthenoflavonoid complexes, the association of a bioactive ligand—the flavonoid itself—is often expected to bring a synergic action with the ruthenium centre, leading with superior activity. This effect is, nevertheless, not straightforward as it was observed for the majority of ruthenium polypyridyl flavonoid complexes [ 31 , 32 ] but not with ruthenium trithiacyclononane flavonoid complexes [ 33 ] nor with some ruthenium p -cymene flavonoid complexes [ 34 , 35 , 36 ].…”

Section: Discussionmentioning

confidence: 95%

“…Three ruthenium trithiacyclononane complexes, having the ligands 7,3′,4′-trihydroxyflavone (THFLV), chrysin (or 5,7-dihydoxyflavone) and tectochrysin (or 5-hydroxy-7-methoxyflavone), were recently reported ( Figure 7 ) [ 33 ]. Interestingly, coordination with 7,3′,4′-trihydroxyflavone occurred at the catechol moiety of the B-ring to form a five-membered coordination ring that is the first reported example of ruthenium-catechol coordination in polyaromatic phenolic ligands; note also that the flavone suffered loss of two protons and coordinated as a dianionic ligand to form a neutral complex.…”

Section: Ruthenium Flavonoid Complexes With Cytotoxic Activity In Vitromentioning

confidence: 99%

Redesigning Nature: Ruthenium Flavonoid Complexes with Antitumour, Antimicrobial and Cardioprotective Activities

Santos

Braga

2021

Molecules

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Flavonoids are a class of natural polyphenolic compounds sharing a common 2-phenyl-3,4-dihydro-2H-1-benzopyran (flavan) backbone. Typically known for their antioxidant activity, flavonoids are also being investigated regarding antitumour and antimicrobial properties. In this review, we report on the complexation of both natural and synthetic flavonoids with ruthenium as a strategy to modulate the biological activity. The ruthenoflavonoid complexes are divided into three subclasses, according to their most prominent bioactivity: antitumour, antimicrobial, and protection of the cardiovascular system. Whenever possible the activity of the ruthenoflavonoids is compared with that of commercial drugs for a critical assessment of the feasibility of using them in future clinical applications.

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Ruthenium(II) trithiacyclononane complexes of 7,3′,4′-trihydroxyflavone, chrysin and tectochrysin: Synthesis, characterisation, and cytotoxic evaluation

Cited by 15 publications

References 56 publications

Hydroponically Grown Sanguisorba minor Scop.: Effects of Cut and Storage on Fresh-Cut Produce

Hydroponically Grown Sanguisorba minor Scop.: Effects of Cut and Storage on Fresh-Cut Produce

Anticancer Activity of Half-Sandwich Ru, Rh and Ir Complexes with Chrysin Derived Ligands: Strong Effect of the Side Chain in the Ligand and Influence of the Metal

Redesigning Nature: Ruthenium Flavonoid Complexes with Antitumour, Antimicrobial and Cardioprotective Activities

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