Synthesis, structure and anticancer activity of Zr(IV) complexes with Schiff bases derived from 8-hydroxyquinoline

2nd International Conference on Chemo and Bioinformatics ICCBIKG 2023 (439-442)

АУТОР(И) / AUTHOR(S): Michaela Harmošová, Martin Kello, Mária Vilková, Erika Samoľová, Ivan Potočňák

Е-АДРЕСА / E-MAIL: michaela.krescankova@upjs.student.sk

Download Full Pdf  

DOI: 10.46793/ICCBI23.439H

САЖЕТАК / ABSTRACT:

The Schiff base 2-{[(2-hydroxyphenyl)imino]methyl}quinolin-8-ol (HLH) and its 5,7-dibromo- (HBrLH) and 5,7-diiodo-derivatives (HILH), which were prepared by multi-step organic synthesis, were used to synthesize [Zr(L)2]·2DMF (1), [Zr(BrL)2]·DMF (2), and [Zr(IL)2]·2DMF (3) complexes. The prepared products were characterized by elemental analysis, IR and NMR spectroscopy, which also monitored the stability of the prepared substances in DMSO, and in the case of HBrLH, HILH and 3, also by single crystal X-ray structural analysis. In the complex 3, two IL ligands are tetradentately bound to the central zirconium(IV) atom via two oxygen and two nitrogen atoms. DMF molecules are outside the coordination sphere. In complexes 1 and 2, we assume an analogous structure. Due to poor solubility, the in vitro cytostatic activity of only complex 2 and its ligand HBrLH was studied against 8 cancer cell lines of different origin (cervix, colon, pancreas, skin, breast, lung, liver and blood) and their selectivity was studied against healthy cell line BJ-5t (human dermal fibroblasts). HBrLH is comparably active to the reference drug, cisplatin, but complex 2 showed lower biological activity. Selectivity of 2 or HBrLH was not observed.

КЉУЧНЕ РЕЧИ / KEYWORDS:

zirconium, 8-hydroxyquinoline, cytotoxic activity

ЛИТЕРАТУРА / REFERENCES:

  • L. Kelland., The resurgence of platinum-based cancer chemotherapy, Nature Reviews Cancer, 7(8) 2007 573–584).
  • F. Bray, J. Ferlay, I. Soerjomataram, R. L. Siegel, L. A. Torre, A. Jemal., Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries, CA: A Cancer Journal for Clinicians, 68(6) 2018 394–424.
  • R. Gupta, V. Luxami, K. Paul., Insights of 8-hydroxyquinolines: A novel target in medicinal chemistry, Bioorganic Chemistry, 108 (2021) 104633.
  • X. Zhou., Insights of metal 8-hydroxylquinolinol complexes as the potential anticancer drugs, Journal of Inorganic Biochemistry, 238 (2023) 112051.
  • H. Saadeh, K. Sweidan, M. Mubarak., Recent Advances in the Synthesis and Biological Activity of 8-Hydroxyquinolines, Molecules, 25 (2020) 4321.
  • M. Y. Wu, G. Esteban, S. Brogi, M. Shionoya, L. Wang, G. Campiani, M. Unzeta, T. Inokuchi, S. Butini, J. Marco-Contelles., Donepezil-like multifunctional agents: Design, synthesis, molecular modeling and biological evaluation, European Journal of Medicinal Chemistry, 121 2016 864–879.
  • A. Basak, Y. Abouelhassan, V. M. Norwood, F. Bai, M. T. Nguyen, S. Jin, R. W. Huigens., Synthetically Tuning the 2-Position of Halogenated Quinolines: Optimizing Antibacterial and Biofilm Eradication Activities via Alkylation and Reductive Amination Pathways, Chemistry – A European
    Journal, 22(27) 2016 9181–9189.
  • D. González, R. Arrué, E. Matamala-Cea, R. Arancibia, P. Hamon, O. Cador, T. Roisnel, J. R Hamon, N. Novoa., Homoleptic CoII, NiII, CuII, and ZnII Complexes Based on 8- Hydroxylquinoline Schiff Base Derivative: a Combined Synthetic, Spectral, Structural, and Magnetic Study, European Journal of Inorganic Chemistry, 2018(43) (2018) 4720–4730.