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Cytotoxic oxidovanadium(IV) complexes of tridentate halogen‐substituted Schiff bases: First dinuclear V(IV) complexes with O → VIV = O → VIV = O core


Rudbari, Hadi Amiri; Saadati, Arezoo; Aryaeifar, Mahnaz; Correia, Isabel; Marques, Fernanda; Blacque, Olivier; Micale, Nicola (2021). Cytotoxic oxidovanadium(IV) complexes of tridentate halogen‐substituted Schiff bases: First dinuclear V(IV) complexes with O → VIV = O → VIV = O core. Bioorganic & Medicinal Chemistry Letters, 49:128285.

Abstract

The reaction of potentially N,N,O-tridentate Schiff base ligands, Cl-LH, Br-LH, BrCl-LH and H-LH, with [VIVO (acac)2] in 2:1 ratio in methanol gave the corresponding mononuclear and dinuclear oxidovanadium(IV) complexes, VO(Cl-L)2 (1), VO(Br-L)2 (2), [(BrCl-L)2(H2O)V(mu-O)VO(BrCl-L)2] (3) and [(H-L)2(H2O)V(mu -O)VO(H-L)2] (4), in good yields. The ligands and complexes were fully characterized by elemental analysis and FT-IR spectroscopy. The ligands were also characterized by 1H NMR spectroscopy. The oxidation state of V(IV)O with d1 configuration in all synthesized complexes was confirmed by EPR. Moreover, the structures of 2 and 3 were determined by X-ray diffraction (XRD) analysis which revealed them as mono- and dinuclear vanadium(IV) complexes, respectively, with the ligands coordinated as bidentate chelates. The structure of 3 represents the first example of dinuclear V(IV) complex with O -> VIV = O -> VIV = O core (Cambridge Structural Database (CSD), version 5.42, update of May 2021). The cytotoxicity of ligands and complexes was evaluated towards ovarian (A2780), breast (MCF7) and prostate (PC3) cancer cells at 48 h. While ligands showed modest IC50 values (>42 mu M), all complexes turned out to be effective in the range 3.9-17.2 mu M. In particular, A2780 and MCF7 cell lines were the most sensitive to the newly synthesized V(IV)O complexes.

Abstract

The reaction of potentially N,N,O-tridentate Schiff base ligands, Cl-LH, Br-LH, BrCl-LH and H-LH, with [VIVO (acac)2] in 2:1 ratio in methanol gave the corresponding mononuclear and dinuclear oxidovanadium(IV) complexes, VO(Cl-L)2 (1), VO(Br-L)2 (2), [(BrCl-L)2(H2O)V(mu-O)VO(BrCl-L)2] (3) and [(H-L)2(H2O)V(mu -O)VO(H-L)2] (4), in good yields. The ligands and complexes were fully characterized by elemental analysis and FT-IR spectroscopy. The ligands were also characterized by 1H NMR spectroscopy. The oxidation state of V(IV)O with d1 configuration in all synthesized complexes was confirmed by EPR. Moreover, the structures of 2 and 3 were determined by X-ray diffraction (XRD) analysis which revealed them as mono- and dinuclear vanadium(IV) complexes, respectively, with the ligands coordinated as bidentate chelates. The structure of 3 represents the first example of dinuclear V(IV) complex with O -> VIV = O -> VIV = O core (Cambridge Structural Database (CSD), version 5.42, update of May 2021). The cytotoxicity of ligands and complexes was evaluated towards ovarian (A2780), breast (MCF7) and prostate (PC3) cancer cells at 48 h. While ligands showed modest IC50 values (>42 mu M), all complexes turned out to be effective in the range 3.9-17.2 mu M. In particular, A2780 and MCF7 cell lines were the most sensitive to the newly synthesized V(IV)O complexes.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biochemistry
Life Sciences > Molecular Medicine
Life Sciences > Molecular Biology
Life Sciences > Pharmaceutical Science
Life Sciences > Drug Discovery
Life Sciences > Clinical Biochemistry
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Organic Chemistry, Clinical Biochemistry, Drug Discovery, Pharmaceutical Science, Molecular Biology, Molecular Medicine, Biochemistry
Language:English
Date:1 October 2021
Deposited On:29 Sep 2021 15:05
Last Modified:30 Sep 2021 20:00
Publisher:Elsevier
ISSN:0960-894X
OA Status:Closed
Publisher DOI:https://doi.org/10.1016/j.bmcl.2021.128285

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