Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes
Ribeiro, Nádia (Universidade de Lisboa. Departamento de Engenharia Química)
Bulut, Ipek (Koç University. School of Medicine)
Pósa, Vivien (University of Szeged. Department of Inorganic and Analytical Chemistry)
Sergi, Baris (Koç University. School of Medicine)
Sciortino, Giuseppe (Institut d'Investigacions Químiques de Catalunya)
Costa Pessoa, João (Universidade de Lisboa. Departamento de Engenharia Química)
Maia, Luisa B. (Universidade Nova de Lisboa. LAQV/REQUIMTE)
Ugone, Valeria (Consiglio Nazionale delle Ricerche. Istituto di Chimica Biomolecolare)
Garribba, Eugenio (Università di Sassari. Dipartimento di Medicina, Chirurgia e Farmacia)
Enyedy, Éva A. (University of Szeged. Department of Inorganic and Analytical Chemistry)
Acilan, Ceyda (Koç University. School of Medicine)
Correia, Isabel (Universidade de Lisboa. Departamento de Engenharia Química)

Fecha:	2022
Descripción:	17 pàg.
Resumen:	We report the synthesis and characterization of a family of benzohydrazones (Ln, n = 1-6) derived from 2-carbaldehyde-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 L4 (Me-substituted) and L6 (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 L4 and L6, 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 μM) than in A-549 cells (IC50 > 20 μM). 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.
Ayudas:	Ministerio de Ciencia e Innovación FJC2019-039135-I
Derechos:	Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial i la comunicació pública de l'obra, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original. No es permet la creació d'obres derivades.
Lengua:	Anglès
Documento:	Article ; recerca ; Versió publicada
Materia:	8-hydroxyquinoline derivatives ; Anticancer ; Oxidovanadium(IV) complexes ; Schiff bases ; Solution stability ; Speciation ; SDG 3 - Good Health and Well-being
Publicado en:	Journal of Inorganic Biochemistry, Vol. 235 (Oct. 2022) , art. 111932, ISSN 1873-3344

DOI: 10.1016/j.jinorgbio.2022.111932
PMID: 35940023

17 p, 5.3 MB

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