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

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 spectrosc...

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Main Authors: Petrasheuskaya Tatsiana
Kovács Ferenc
Igaz Nóra
Rónavári Andrea
Hajdu Bálint
Nagyné Bereczki Laura
May Nóra Veronika
Spengler Gabriella
Gyurcsik Béla
Csontné Kiricsi Mónika
Nagyné Frank Éva
Enyedy Éva Anna
Format: Article
Published: 2023
Series:MOLECULES 28 No. 1
Subjects:
doi:10.3390/molecules28010054

mtmt:33416616
Online Access:http://publicatio.bibl.u-szeged.hu/25875
Description
Summary: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.
Physical Description:26
ISSN:1420-3049