A comparative study on the complex formation of 2-aminoestradiol and 2-aminophenol with divalent metal ions: solution chemistry and anticancer activity

Petrasheuskaya, Tatsiana and Kovács, Ferenc and Spengler, Gabriella and May, Nóra Veronika and Nagyné Frank, Éva and Enyedy, Éva Anna (2022) A comparative study on the complex formation of 2-aminoestradiol and 2-aminophenol with divalent metal ions: solution chemistry and anticancer activity. JOURNAL OF MOLECULAR STRUCTURE, 1261. No. 132858. ISSN 0022-2860

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Abstract

The effects of the the complexation of 2-aminophenol to 2-aminoestradiol (also bearing 2-aminophenol moiety) with some divalent metal ions on various physico-chemical and biological properties were investigated. Namely, proton dissociation of the title compounds and their complex formation with Cu(II), Zn(II) and Ni(II) ions in addition to antibacterial and antitumor activities were studied. Stability of the complexes was characterized in solution by pH-potentiometry. Ligands coordinating via (O,N) donor set form mono and bis complexes with the studied metal ions. Significantly higher stability was found for the Cu(II) complexes of both ligands in comparison to the other two metal ions. Furthermore, the Cu(II) – 2-aminoestradiol complex was isolated and characterized by UV-visible and electron paramagnetic resonance spectroscopy in order to confirm the suggested coordination mode. The compounds did not show measurable antibacterial activity, while 2-aminoestradiol displayed high cytotoxic activity on HeLa, Colo 205 and the doxorubicin-resistant Colo 320 cells, and 2-aminophenol was found to be non-toxic on all tested cancer cells. Complexation with Ni(II) ions increased cytotoxicity of the ligands while in the pres- ence of Zn(II) it was decreased. Complex formation with Cu(II) ions induced higher cytotoxicity of 2-aminophenol on all tested cancer cells, whereas for 2-aminoestradiol, complexation was advantages only in the case of MCF-7 cancer cells. Moreover, complexation with Cu(II) ions significantly increased the antioxidant activity of both tested aminophenols and resulted in higher percentage of apoptotic cells.

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