Fe(III) and Cu(II) Complexes of Chlorogenic Acid: Spectroscopic, Thermal, Anti-/Pro-Oxidant, and Cytotoxic Studies
Monika Kalinowska,
Kamila Gryko,
Ewelina Gołębiewska,
Grzegorz Świderski,
Hanna Lewandowska,
Marek Pruszyński,
Małgorzata Zawadzka,
Maciej Kozłowski,
Justyna Sienkiewicz-Gromiuk,
Włodzimierz Lewandowski
Affiliations
Monika Kalinowska
Department of Chemistry, Biology and Biotechnology, Institute of Environmental Engineering and Energetics, Faculty of Civil Engineering and Environmental Sciences, Białystok University of Technology, Wiejska 45E Street, 15-351 Bialystok, Poland
Kamila Gryko
Department of Chemistry, Biology and Biotechnology, Institute of Environmental Engineering and Energetics, Faculty of Civil Engineering and Environmental Sciences, Białystok University of Technology, Wiejska 45E Street, 15-351 Bialystok, Poland
Ewelina Gołębiewska
Department of Chemistry, Biology and Biotechnology, Institute of Environmental Engineering and Energetics, Faculty of Civil Engineering and Environmental Sciences, Białystok University of Technology, Wiejska 45E Street, 15-351 Bialystok, Poland
Grzegorz Świderski
Department of Chemistry, Biology and Biotechnology, Institute of Environmental Engineering and Energetics, Faculty of Civil Engineering and Environmental Sciences, Białystok University of Technology, Wiejska 45E Street, 15-351 Bialystok, Poland
Hanna Lewandowska
Institute of Nuclear Chemistry and Technology, 16 Dorodna Street, 03-195 Warsaw, Poland
Marek Pruszyński
Institute of Nuclear Chemistry and Technology, 16 Dorodna Street, 03-195 Warsaw, Poland
Małgorzata Zawadzka
Department of Chemistry, Biology and Biotechnology, Institute of Environmental Engineering and Energetics, Faculty of Civil Engineering and Environmental Sciences, Białystok University of Technology, Wiejska 45E Street, 15-351 Bialystok, Poland
Maciej Kozłowski
Department of Chemistry, Biology and Biotechnology, Institute of Environmental Engineering and Energetics, Faculty of Civil Engineering and Environmental Sciences, Białystok University of Technology, Wiejska 45E Street, 15-351 Bialystok, Poland
Justyna Sienkiewicz-Gromiuk
Department of General and Coordination Chemistry and Crystallography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Sklodowska University, Maria Curie-Sklodowska Sq. 2, 20-031 Lublin, Poland
Włodzimierz Lewandowski
Department of Chemistry, Biology and Biotechnology, Institute of Environmental Engineering and Energetics, Faculty of Civil Engineering and Environmental Sciences, Białystok University of Technology, Wiejska 45E Street, 15-351 Bialystok, Poland
Complexes of chlorogenic acid (5-CQA) with copper(II) and iron(III) were synthesized in a solid state and examined by means of FT-IR, thermogravimetric, and elemental analyses. The molar stoichiometric ratios of metal:ligand for the solid forms of the complexes were established as Cu(II):L = 1:2 and Fe(III):L = 2:3 (L: 5-CQA), with the possible coordination through the carboxylate group and the hydroxyl group from the catechol moiety. In an aqueous solution at pH = 7.4, the composition of the complexes was Cu(II):L = 1:1, and Fe(III):L = 1:1 and 1:2. The Cu(II) and Fe(III) complexes with 5-CQA showed lower antioxidant properties, as estimated by the spectrophotometric methods with DPPH•, ABTS•+, and HO• radicals, than the ligand alone, whereas in the lipid peroxidation inhibition assay, the metal complexes revealed a higher antioxidant activity than 5-CQA. Cu(II) 5-CQA showed the highest pro-oxidant activity in the Trolox oxidation assays compared to the other studied compounds. The lipophilic parameters of the compounds were estimated using the HPLC method. 5-CQA and its complexes with Fe(III) and Cu(II) were not toxic to HaCaT cells in a tested concentration range of 0.15–1000 nM after a 24 h incubation time.
