Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes

Ribeiro, Nádia; Bulut, Ipek; Pósa, Vivien; Sergi, Baris; Sciortino, Giuseppe; Pessoa, João Costa; Maia, Luísa B.; Ugone, Valeria; Garribba, Eugenio; Enyedy, Éva A.; Acılan, Ceyda; Correia, Isabel

doi:10.1016/j.jinorgbio.2022.111932

Cited by 17 publications

(36 citation statements)

References 76 publications

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“…The infra-red absorption spectra (FTIR, Supplementary Figure S1 ) of the two new ligand precursors are consistent with those already reported for the related compounds ( Ribeiro et al, 2022 ), presenting narrow, strong bands in the region around 3,400 cm −1 , assigned to OH and NH stretching vibrations. A set of bands between 1,680 and 1,500 cm −1 , due to vibrations of double bonds in the carbonyl and imine moieties, as well as in the aromatic rings, is observed.…”

Section: Resultssupporting

confidence: 88%

“…All compounds were characterized by UV-Vis absorption spectroscopy in DMSO ( Supplementary Table S3 , Supplementary Figure S3, S4 ). The organic compounds, L 1 -L 8 , show electronic transitions typical for this type of compounds, namely, π→π* and n→π* transitions ( Liu and Yang, 2009b ; Ribeiro et al, 2022 ). Cu(II) complexes spectra show the presence of the same bands, although shifted, and new ones at higher wavelengths with lower molar extinction coefficients, consistent with charge transfer bands between the ligand and the metal centre.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of the ligand precursors was done by adapting a published procedure ( Liu and Yang, 2009a ) – Scheme 1 . The synthesis and characterization of L 1 -L 6 were described in a previous publication ( Ribeiro et al, 2022 ). Briefly, the carbaldehyde was dissolved in ca.…”

Section: Methodsmentioning

confidence: 99%

“…Numerous studies provided proof of the direct relationship between the ability of these molecules to act as metal chelators and their antiproliferative activity ( Prachayasittikul et al, 2013 ). Binding of biologically active molecules to metal ions may alter their pharmacokinetic characteristics and improve their therapeutic potential, thus the prospective synergistic effect of having the 8HQ scaffold, with known therapeutic activity ( Zhai et al, 2010 ; Jiang et al, 2011 ; Oliveri et al, 2012 ; Prachayasittikul et al, 2013 ; Song et al, 2015 ; Oliveri and Vecchio, 2016 ; Gupta et al, 2021 ), chelated to a metal ion, with its potential for involvement in redox processes and its diversity in structure and electronic features, has been considered an attractive approach to develop therapeutic drugs ( Correia et al, 2014 ; Ndagi et al, 2017 ; Pape et al, 2018 ; Matos et al, 2019 ; Ribeiro et al, 2022 ). For example, zinc and copper complexes of 5,7-dihalo-substituted-8-hydroxyquinolines were reported as highly cytotoxic agents against hepatoma, ovarian and non-small-cell lung human tumour cells, with IC 50 values from 1.4 nM to 32.13 μM ( Liu et al, 2013 ).…”

Section: Introductionmentioning

confidence: 99%

“…Recently, we reported on a series of six 8HQ-benzohydrazones and their coordination to V(IV)O ions ( Ribeiro et al, 2022 ). Cytotoxicity on a melanoma cell line occurred in the low micromolar range and increased generation of ROS-induced DNA damage was observed.…”

Section: Introductionmentioning

confidence: 99%

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Promising anticancer agents based on 8-hydroxyquinoline hydrazone copper(II) complexes

et al. 2023

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We report the synthesis and characterization of a group of benzoylhydrazones (Ln) derived from 2-carbaldehyde-8-hydroxyquinoline and benzylhydrazides containing distinct para substituents (R = H, Cl, F, CH3, OCH3, OH and NH2, for L1-7, respectively; in L8 isonicotinohydrazide was used instead of benzylhydrazide). Cu(II) complexes were prepared by reaction of each benzoylhydrazone with Cu(II) acetate. All compounds were characterized by elemental analysis and mass spectrometry as well as by FTIR, UV-visible absorption, NMR or electron paramagnetic resonance spectroscopies. Complexes isolated in the solid state (1–8) are either formulated as [Cu(HL)acetate] (with L1 and L4) or as [Cu(Ln)]3 (n = 2, 3, 5, 6, 7 and 8). Single crystal X-ray diffraction studies were done for L5 and [Cu(L5)]3, confirming the trinuclear formulation of several complexes. Proton dissociation constants, lipophilicity and solubility were determined for all free ligands by UV-Vis spectrophotometry in 30% (v/v) DMSO/H2O. Formation constants were determined for [Cu(LH)], [Cu(L)] and [Cu(LH−1)] for L = L1, L5 and L6, and also [Cu(LH−2)] for L = L6, and binding modes are proposed, [Cu(L)] predominating at physiological pH. The redox properties of complexes formed with L1, L5 and L6 are investigated by cyclic voltammetry; the formal redox potentials fall in the range of +377 to +395 mV vs. NHE. The binding of the Cu(II)-complexes to bovine serum albumin was evaluated by fluorescence spectroscopy, showing moderate-to-strong interaction and suggesting formation of a ground state complex. The interaction of L1, L3, L5 and L7, and of the corresponding complexes with calf thymus DNA was evaluated by thermal denaturation. The antiproliferative activity of all compounds was evaluated in malignant melanoma (A-375) and lung (A-549) cancer cells. The complexes show higher activity than the corresponding free ligand, and most complexes are more active than cisplatin. Compounds 1, 3, 5, and 8 were selected for additional studies: while these complexes induce reactive oxygen species and double-strand breaks in both cancer cells, their ability to induce cell-death by apoptosis varies. Within the set of compounds tested, 8 emerges as the most promising one, presenting low IC50 values, and high induction of oxidative stress and DNA damage, which eventually lead to high rates of apoptosis.

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Section: Resultssupporting

confidence: 88%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Promising anticancer agents based on 8-hydroxyquinoline hydrazone copper(II) complexes

et al. 2023

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Vanadium(V) Pyridine‐Containing Schiff Base Catecholate Complexes are Lipophilic, Redox‐Active and Selectively Cytotoxic in Glioblastoma (T98G) Cells

Kostenkova

Levina

Walters

et al. 2023

Chemistry A European J

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Two new series of complexes with pyridine‐containing Schiff bases, [VVO(SALIEP)L] and [VVO(Cl‐SALIEP)L] (SALIEP = N‐(salicylideneaminato)‐2‐(2‐aminoethylpyridine; Cl‐SALIEP = N‐(5‐chlorosalicylideneaminato)‐2‐(2‐aminoethylpyridine, L = catecholato(2‐) ligand) were synthesized. Characterization by 1H and 51V NMR and UV‐Vis spectroscopies confirmed that: 1) most complexes form two major geometric isomers in solution, and [VVO(SALIEP)(DTB)] (DTB = di‐tert‐butylcatecholato(2‐)) forms two isomers that equilibrate in solution; and 2) tert‐butyl substituents was necessary to stabilize the reduced V(IV) species (EPR spectroscopy and cyclic voltammetry). The pyridine moiety within the Schiff base ligands significantly changed their chemical properties with unsubstituted catecholate ligands compared with the parent HSHED (N‐(salicylideneaminato)‐Nˊ‐(2‐hydroxyethyl)‐1,2‐ethanediamine) Schiff base complexes. Immediate reduction to V(IV) occurred for the unsubstituted‐catecholato V(V) complexes on dissolution in DMSO. By contrast, the pyridine moiety within the Schiff base significantly improved the hydrolytic stability of [VVO(SALIEP)(DTB)] compared with [VVO(HSHED)(DTB)]. [VVO(SALIEP)(DTB)] had moderate stability in cell culture media. There was significant cellular uptake of the intact complex by T98g (human glioblastoma) cells and very good anti‐proliferative activity (IC50 6.7 ± 0.9 μM, 72 h), which was ~five‐fold higher compared with the non‐cancerous human cell line, HFF‐1 (IC50 34 ± 10 μM). This made it a potential drug candidate for the treatment of advanced gliomas by intracranial injections.

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Correlation of the anticancer and pro-oxidant behavior and the structure of flavonoid-oxidovanadium(IV) complexes

Naso

Ferrer

Williams

2023

Coordination Chemistry Reviews

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Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes

Cited by 17 publications

References 76 publications

Promising anticancer agents based on 8-hydroxyquinoline hydrazone copper(II) complexes

Promising anticancer agents based on 8-hydroxyquinoline hydrazone copper(II) complexes

Vanadium(V) Pyridine‐Containing Schiff Base Catecholate Complexes are Lipophilic, Redox‐Active and Selectively Cytotoxic in Glioblastoma (T98G) Cells

Correlation of the anticancer and pro-oxidant behavior and the structure of flavonoid-oxidovanadium(IV) complexes

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