Chelating ability and biological activity of hesperetin Schiff base
PBN-AR
Instytucja
Centrum Badań Molekularnych i Makromolekularnych Polskiej Akademii Nauk
Informacje podstawowe
Główny język publikacji
en
Czasopismo
JOURNAL OF INORGANIC BIOCHEMISTRY
ISSN
0162-0134
EISSN
Wydawca
ELSEVIER SCIENCE INC
DOI
URL
Rok publikacji
2015
Numer zeszytu
Strony od-do
34-47
Numer tomu
143
Link do pełnego tekstu
Liczba arkuszy
Słowa kluczowe
en
Flavonoids
Hesperetin Schiff bases
Copper complexes
Metal–ionophore complexes
Streszczenia
Język
en
Treść
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 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.
Cechy publikacji
ORIGINAL_ARTICLE
Inne
System-identifier
586247
CrossrefMetadata from Crossref logo
Cytowania
Liczba prac cytujących tę pracę
Brak danych
Referencje
Liczba prac cytowanych przez tę pracę
Brak danych