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

Author:

Kostenkova Kateryna1ORCID,Levina Aviva2ORCID,Walters Drew A.1,Murakami Heide A.1ORCID,Lay Peter A.2ORCID,Crans Debbie C.1ORCID

Affiliation:

1. Department of Chemistry and The Cell and Molecular Biology Program Colorado State University 1301 Center Ave Chemistry B101 Campus Delivery 1872 Fort Collins CO 80523-1872 USA

2. School of Chemistry and Sydney Analytical The University of Sydney Sydney NSW 2006 Australia

Abstract

AbstractTwo 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‐aminoethyl)pyridine, L=catecholato(2−) ligand) have been 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=3,5‐di‐tert‐butylcatecholato(2−)) forms two isomers that equilibrate in solution; and 2) tert‐butyl substituents were necessary to stabilize the reduced VIV 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)‐N′‐(2‐hydroxyethyl)‐1,2‐ethanediamine) Schiff base complexes. Immediate reduction to VIV occurred for the unsubstituted‐catecholato VV 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 approximately five times higher than for the non‐cancerous human cell line, HFF‐1 (IC50 34±10 μM). This made [VVO(SALIEP)(DTB)] a potential drug candidate for the treatment of advanced gliomas by intracranial injection.

Funder

Australian Research Council

Colorado State University

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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