Csuvik Oszkár

Enyedy Éva Anna

Fülöp Ferenc

May Nóra V.

Safyanova Inna

Szatmári István

English

University of Szeged

26th International Symposium on Analytical and Environmental Problems 302  COMPLEX FORMATION OF COPPER(II) WITH A PROLINE SUBSTITUTED 8-HYDROXYQUINOLINE: SOLUTION STUDIES AND STRUCTURAL CHARACTERIZATION  Inna Safyanova1, Nóra V. May2, Oszkár Csuvik3, Ferenc Fülöp3, István Szatmári3, Eva A. Enyedy1  1Department of Inorganic and Analytical Chemistry, Interdisciplinary Excellence Centre and MTA-SZTE Lendület Functional Metal Complexes Research Group, University of Szeged, H-6720 Szeged, Dóm tér 7, Hungary 2Chemical Crystallography Research Laboratory, Research Centre for Natural Sciences, Magyar Tudósok Körútja 2, H-1117 Budapest, Hungary 3Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary e-mail: sssafyanova@gmail.com  Abstract 8-hydroxyquinoline and its substituted derivatives are a well-known class of bidentate ligands widely used in bioanalytical and supramolecular chemistry due to wide specter of their applications and high coordination binding activity [1, 2]. 8-hydroxyquinolines and their metal complexes often exhibit anticancer activity [2], and the most prominent example is orally active tris(8-hydroxyquinolato)gallium(III), which is tested under clinical trials phase I and II [3]. The cytotoxicity of 8-hydroxyquinolines is also related to complexation with endogenous metals such as the redox active copper and iron ions [4]. 8-Hydroxyquinolines generally suffer from limited water solubility, and in this work a more water soluble D-proline hybrid molecule, (D)-5-chloro-7-((proline-1-yl)methyl)8-hydroxyquinoline (8HQCl-D-Pro, Fig. 1.a), was developed and its complexation with copper(II) was investigated. .                              a b Figure 1. a) Scheme of 8HQCl-D-Pro ligand; b) Crystal structure of 8HQCl-D-Pro.  The ligand was synthesized similarly as the analogous 8HQCl-L-Pro in our previous work [5].The solution equilibrium processes of 8HQCl-D-Pro, whose crystal structure was obtained and determined by X-ray analysis (Fig. 1.b), with copper(II) was investigated in a 30% (v/v) dmso/water solvent mixture using pH-potentiometry and UV-visible spectroscopy. A model containing mononuclear [Cu(LH)]+, [Cu(L2H)]‒ and [Cu(LH)2] species is proposed (Fig. 2).  26th International Symposium on Analytical and Environmental Problems 303    a b Figure 2. a) a) UV-visible absorption spectra of 8HQCl-D-Pro at pH range 1.9–12.6 in a 30% (v/v) DMSO/H2O solvent mixture; b) individual UV-visible absorption spectra of the different complexes (red lines) and ligand species (black lines) calculated for the Cu(II) – 8HQCl-D-Pro system (cligand = 42,5 μM; cCu(II) = 23 μM; T = 25.0 °C; I = 0.1 M (KCl), l = 1 cm).  Acknowledgements This work was supported by the National Research, Development and Innovation Office-NKFIA through project GINOP-2.3.2-15-2016-00038 and Ministry of Human Capacities, Hungary grant, TKP-2020. Visegrad Scholarship 52010718 (I. S.).  References [1] Y. Song, H. Xu, W. Chen, P. Zhan and X. Liu, Med. Chem. Commun. 6 (2015) 61.  [2] A. R. Timerbaev, Metallomics. 1 (2009) 193. [3] U. Jungwirth, J. Gojo, T. Tuder, G. Walko, M. Holcmann, T. Schöfl, K. Nowikovsky, N. Wilfinger, S. Schoonhoven, C.R. Kowol, R. Lemmens-Gruber, P. Heffeter, B.K. Keppler, W. Berger, Mol. Cancer Ther. 13 (2014) 2436. [4] V. Oliveri and G. Vecchio, Eur. J. Med. Chem. 120 (2016) 252. [5] J. P. Mészáros, J. M. Poljarevic, I. Szatmári, O. Csuvik, F. Fülöp, N. Szoboszlai, G. Spengler, É. A. Enyedy, Dalton Trans. 49 (2020) 7977.     0.000.050.100.150.200.25270 320 370 420 470Absorbance / nm2.42 1.773.709.2312.60020004000600080001000012000270 320 370 420 470/ M-1cm-1 / nmH3L+H2LHL-L2-[Cu(LH)]+[Cu(LH)2][Cu(L2H)]-

Complex formation of copper (II) with a proline substituted 8-hydroxyquinoline : solution studies and structural characterization

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Complex formation of copper (II) with a proline substituted 8-hydroxyquinoline : solution studies and structural characterization

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