title: Chelating ability and biological activity of hesperetin Schiff base.
abstract: Hydrazone hesperetin Schiff base (HHSB) - N-[(±)-[5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)chroman-4-ylidene]amino]benzamide has been synthesized and its crystal structure was determined. This compound was used for the formation of Cu(II) complexes in solid state and in solution which were characterized using different spectroscopic methods. The analyses of potentiometric titration curves revealed that monomeric and dimeric complexes of Cu(II) are formed above pH7. The ESI-MS (electrospray ionization-mass spectrometry) spectra confirmed their formation. The EPR and UV-visible spectra evidenced the involvement of oxygen and nitrogen atoms in Cu(II) coordination. Hydrazone hesperetin Schiff base can show keto-enol tautomerism and coordinate Cu(II) in the keto (O(-), N, Oket) and in the enolate form (O(-), N, O(-)enol). The semi-empirical molecular orbital method PM6 and DFT (density functional theory) calculations have revealed that the more stable form of the dimeric complex is that one in which the ligand is present in the enol form. The CuHHSB complex has shown high efficiency in the cleavage of plasmid DNA in aqueous solution, indicating its potential as chemical nuclease. Studies on DNA interactions, antimicrobial and cytotoxic activities have been undertaken to gain more information on the biological significance of HHSB and copper(II)-HHSB chelate species.
authors.affiliation: Faculty of Biotechnology and Food Chemistry, Lodz University of Technology, Stefanowskiego Street 4/10, 90-924 Lodz, Poland. Electronic address: elalodyg@p.lodz.pl.
authors.forename: Elzbieta
authors.initials: E
authors.lastname: Lodyga-Chruscinska
authors.affiliation: Faculty of Biotechnology and Food Chemistry, Lodz University of Technology, Stefanowskiego Street 4/10, 90-924 Lodz, Poland.
authors.forename: Marzena
authors.initials: M
authors.lastname: Symonowicz
authors.affiliation: Faculty of Biotechnology and Food Chemistry, Lodz University of Technology, Stefanowskiego Street 4/10, 90-924 Lodz, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Sykula
authors.affiliation: Faculty of Biotechnology and Food Chemistry, Lodz University of Technology, Stefanowskiego Street 4/10, 90-924 Lodz, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Bujacz
authors.affiliation: Dipartimento di Chimica e Farmacia, Centro Interdisciplinare per lo Sviluppo della Ricerca Biotecnologica e per lo Studio della Biodiversità della Sardegna, Università di Sassari, via Vienna 2, I-07100 Sassari, Italy.
authors.forename: Eugenio
authors.initials: E
authors.lastname: Garribba
authors.affiliation: Department of Chemistry, University of Wroclaw, F. Joliot-Curie Street 14, 50-383 Wroclaw, Poland.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Rowinska-Zyrek
authors.affiliation: Intercollegiate Faculty of Biotechnology, University of Gdansk and Medical University of Gdansk, Kladki 24, 80-922 Gdansk, Poland.
authors.forename: Stanislaw
authors.initials: S
authors.lastname: Oldziej
authors.affiliation: Faculty of Biotechnology and Food Chemistry, Lodz University of Technology, Stefanowskiego Street 4/10, 90-924 Lodz, Poland.
authors.forename: Elzbieta
authors.initials: E
authors.lastname: Klewicka
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza Street 112, 90-363 Lodz, Poland.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Janicka
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza Street 112, 90-363 Lodz, Poland.
authors.forename: Karolina
authors.initials: K
authors.lastname: Krolewska
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza Street 112, 90-363 Lodz, Poland.
authors.forename: Marcin
authors.initials: M
authors.lastname: Cieslak
authors.affiliation: Faculty of Biotechnology and Food Chemistry, Lodz University of Technology, Stefanowskiego Street 4/10, 90-924 Lodz, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Brodowska
authors.affiliation: Faculty of Process and Environmental Engineering, Lodz University of Technology, Wolczanska 175, 90-924 Lodz, Poland.
authors.forename: Longin
authors.initials: L
authors.lastname: Chruscinski
mesh_terms: D002614:Chelating Agents / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D044950:Flavanones / Q000737:chemistry*; D006569:Hesperidin; D010957:Plasmids / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry
chemical_list: D002614:Chelating Agents; D044950:Flavanones; D012545:Schiff Bases; D003300:Copper; D004247:DNA; D006569:Hesperidin; C013015:hesperetin
keywords: Copper complexes; Flavonoids; Hesperetin; Metal–ionophore complexes; Schiff bases