Estradiol-Based Salicylaldehyde (Thio)semicarbazones and Their Copper Complexes with Anticancer, Antibacterial and Antioxidant Activities

Petrasheuskaya, Tatsiana and Kovács, Ferenc and Igaz, Nóra and Rónavári, Andrea and Hajdu, Bálint and Nagyné Bereczki, Laura and May, Nóra Veronika and Spengler, Gabriella and Gyurcsik, Béla and Csontné Kiricsi, Mónika and Nagyné Frank, Éva and Enyedy, Éva Anna (2023) Estradiol-Based Salicylaldehyde (Thio)semicarbazones and Their Copper Complexes with Anticancer, Antibacterial and Antioxidant Activities. MOLECULES, 28 (1). No.-54. ISSN 1420-3049

Preview

Text Molecules_2023_28-54.pdf Available under License Creative Commons Attribution. Download (5MB) | Preview

Abstract

A series of novel estradiol-based salicylaldehyde (thio)semicarbazones ((T)SCs) bearing (O,N,S) and (O,N,O) donor sets and their Cu(II) complexes were developed and characterized in detail by 1H and ¹³C nuclear magnetic resonance spectroscopy, UV–visible and electron paramagnetic resonance spectroscopy, electrospray ionization mass spectrometry and elemental analysis. The structure of the Cu(II)-estradiol-semicarbazone complex was revealed by X-ray crystallography. Proton dissociation constants of the ligands and stability constants of the metal complexes were determined in 30% (v/v) DMSO/H2O. Estradiol-(T)SCs form mono-ligand complexes with Cu(II) ions and exhibit high stability with the exception of estradiol-SC. The Cu(II) complexes of estradiol-TSC and its N,N-dimethyl derivative displayed the highest cytotoxicity among the tested compounds in MCF-7, MCF-7 KCR, DU-145, and A549 cancer cells. The complexes do not damage DNA according to both in vitro cell-free and cellular assays. All the Cu(II)-TSC complexes revealed significant activity against the Gram-positive Staphylococcus aureus bacteria strain. Estradiol-TSCs showed efficient antioxidant activity, which was decreased by complexation with Cu(II) ions. The exchange of estrone moiety to estradiol did not result in significant changes to physico-chemical and biological properties.

Actions (login required)

Edit Item