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Chelating ability and biological activity of hesperetin Schiff base

Łodyga-Chruscińska, Elżbieta and Symonowicz, Marzena and Sykula, Anna and Bujacz, Anna and Garribba, Eugenio and Rowinska-Zyrek, Magdalena and Oldziej, Stanislaw and Klewicka, Elżbieta and Janicka, Magdalena and Krolewska, Karolina and Cieslak, Marcin and Brodowska, Katarzyna and Chrusciński, Longin (2015) Chelating ability and biological activity of hesperetin Schiff base. Journal of inorganic biochemistry, Vol. 143 , p. 34-47. ISSN 0162-0134. eISSN 1873-3344. Article.

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DOI: 10.1016/j.jinorgbio.2014.11.005


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 solutionwhichwere characterized using different spectroscopicmethods. The analyses of potentiometric titration curves revealed that monomeric and dimeric complexes of Cu(II) are formed above pH 7. 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 onDNA interactions, antimicrobial and cytotoxic activities have been undertaken to gainmore information on the biological significance of HHSB and copper(II)–HHSB chelate species.

Item Type:Article
ID Code:10620
Uncontrolled Keywords:Flavonoids, hesperetin, schiff bases, Copper complexes, metal–ionophore complexes
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Chimica e Farmacia
Deposited On:14 Jan 2015 17:14

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