Publication Type Journal Article
Title Solution chemical properties and anticancer potential of 8-hydroxyquino-line hydrazones and their oxidovanadium(IV) complexes
Authors Nádia Ribeiro Ipek Bulut Vivien Posa Baris Sergi Giuseppe Sciortino J.C. Pessoa Luisa B. Maia Valeria Ugone Eugenio Garribba Eva A. Enyedy Ceyda Acilan Isabel Correia
Groups BIOIN
Journal JOURNAL OF INORGANIC BIOCHEMISTRY
Year 2022
Month
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Volume 235
Number
Pages
Abstract We report the synthesis and characterization of a family of benzohydrazones (L-n, n = 1-6) derived from 2-car-baldehyde-8-hydroxyquinoline and benzylhydrazides containing different substituents in the para position. Their oxidovanadium(IV) complexes were prepared and compounds with 1:1 and 1:2 metal-to-ligand stoichiometry were obtained. All compounds were characterized by elemental analyses and mass spectrometry as well as FTIR, UV-visible absorption, NMR (ligand precursors) and EPR (complexes) spectroscopies, and by DFT computational methods. Proton dissociation constants, lipophilicity and solubility in aqueous media were determined for all ligand precursors. Complex formation with V(IV)O was evaluated by spectrophotometry for L-4 (Me-substituted) and L-6 (OH-substituted) and formation constants for mono [VO(HL)](+), [VO(L)] and bis [VO(HL)(2)], [VO(HL) (L)], [VO(L)(2)](2- )complexes were determined. EPR spectroscopy indicates the formation of [VO(HL)](+) and [VO (HL)(2)], with this latter being the major species at the physiological pH. Noteworthy, the EPR data suggest a different behaviour for L-4 and L-6, which confirm the results obtained in the solid state. The antiproliferative activity of all compounds was evaluated in malignant melanoma (A-375) and lung (A-549) cancer cells. All complexes show much higher activity on A-375 (IC50 < 6.3 mu M) than in A-549 cells (IC50 > 20 mu M). Complex 3 (F-substituted) shows the lowest IC50 on both cell lines and lower than cisplatin (in A-375). Studies identified this compound as the one showing the highest increase in Annexin-V staining, caspase activity and induction of double stranded breaks, corroborating the cytotoxicity results. The mechanism of action of the complexes involves reactive oxygen species (ROS) induced DNA damage, and cell death by apoptosis.
DOI http://dx.doi.org/10.1016/j.jinorgbio.2022.111932
ISBN
Publisher ELSEVIER SCIENCE INC
Book Title
ISSN 0162-0134
EISSN 1873-3344
Conference Name
Bibtex ID WOS:000848287000001
Observations
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