Enyedy Éva Anna

Hajdu Bálint

Kovács Hilda

Lihi Norbert

May Nóra V.

Szakács Gergely

Szatmári István

English

University of Szeged

30th International Symposium on Analytical and Environmental Problems  325  R7-SUBSTITUTED 8-HYDROXYQUINOLINES WITH MULTIDRUG RESISTANCE SELECTIVITY: SOLUTION CHEMISTRY AND METAL COMPLEXATION  Hilda Kovács1, Bálint Hajdu1, Nóra V. May2, Norbert Lihi3, István Szatmári4, Gergely Szakács5, Éva A. Enyedy1  1Department of Molecular and Analytical Chemistry, Interdisciplinary Excellence Centre, University of Szeged, Dóm tér 7-8, H-6720 Szeged, Hungary 2Centre for Structural Science, Research Centre for Natural Sciences, Hungarian Research Network (HUN-REN), Magyar tudósok körútja 2, H-1117 Budapest, Hungary 3Department of Inorganic and Analytical Chemistry, University of Debrecen, Egyetem tér 1., H-4032 Debrecen, Hungary 4Institute of Pharmaceutical Chemistry and Stereochemistry Research Group, Eötvös Loránd Research Network, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary 5Center for Cancer Research, Medical University of Vienna, Borschkegasse 8a, A-1090 Vienna, Austria e-mail: kovacs.hilda@chem.u-szeged.hu  8-hydroxyquinoline (8HQ) derivatives have a wide range of biological properties, including anticancer activity [1]. 8HQ-based Mannich bases with a methylamine subunit at position 7 (R7) are reported to have notable cytotoxicity, especially against multidrug resistant (MDR) cancer cell lines [2,3]. The biological activity of 8-hydroxyquinolines is often linked to complexation with the endogenous metal ions. The increased cytotoxicity of certain 8HQs on MDR cells is thought to result from either iron deprivation or the formation of redox-active copper(II) complexes [4].  Herein, studies on the interaction of five selected MDR-selective Mannich base HQ derivatives with Fe(II), Fe(III) and Cu(II) ions are presented in terms of solution speciation and redox properties of the forming complexes. The stoichiometry and formation constants of the complexes were determined via UV-visible spectrophotometric titrations. In the case of Cu(II) complexes, circular dichroism and electron paramagnetic resonance spectroscopy were also applied to confirm the coordination modes. To explore the redox properties of the iron and copper complexes cyclic voltammetric and spectroelectrochemical measurements were performed. The properties of the studied complexes are compared with those of non-MDR-selective 8HQs in order to identify differences in their solution chemical behavior.  Acknowledgements This work was supported by the National Research, Development and Innovation Office TKP-2021-EGA-32, the EKÖP-24-3-EKÖP-527 (H. K.) University Research Scholarship Program of the Ministry for Innovation and Technology and the HUN-REN Hungarian Research Network (LP2019-6/2019).  References [1]  Y. Song, H. Xu, W. Chen, P. Zhan, X. Liu, Med. Chem.Commun. 6 (2015) 61–74.  [2] T. Pivarcsik, O. Dömötör, J. P. Mészáros, N. V. May, G. Spengler, O. Csuvik, I. Szatmári, É. A. Enyedy, Int. J. Mol. Sci. 22 (2021) 11281. [3] V. F.S. Pape, A. Gaál, I. Szatmári, N. Kucsma, N. Szoboszlai, C. Streli, F. Fülöp, É. A. Enyedy, G. Szakács, Cancers 13 (2021) 154.  [4] V. F. S. Pape, R. Palkó, S. Tóth, M. J. Szabó, J. Sessler, G. Dormán, É. A. Enyedy, T. Soós, I. Szatmári, G. Szakács, J. Med. Chem. 65 (2022) 7729–7745. 

R7-substituted 8-hydroxyquinolines with multidrug resistance selectivity: solution chemistry and metal complexation : [abstract]

http://acta.bibl.u-szeged.hu/85750/1/proceedings_of_isaep_2024_325.pdf

R7-substituted 8-hydroxyquinolines with multidrug resistance selectivity: solution chemistry and metal complexation : [abstract]

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