Naslov
NMR i teorijska ispitivanja norfloksacina
(NMR and theoretical investigations of norfloxacin)

Autori
Vikić-Topić, Dražen ; Jadrijević-Mladar Takač, Milena ; Pejov, Ljupče

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Knjiga sažetaka, Treći hrvatski kongres farmacije / Zorc, Branka - Zagreb : Farmaceutsko-biokemijski fakultet Sveučilišta u Zagrebu, 2005, 150-150

Skup
Treći hrvatski kongres farmacije s međunarodnim sudjelovanjem

Mjesto i datum
Cavtat, Hrvatska, 27.04.2005. - 30.04.2005

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
fluorokinolonski antibiotici; norfloksacin; kompleksi s ionima metala; semi-empirijski teorijski računi 1D i 2D-NMR; homo- i heteronuklearna 1H i 13 C NMR spektroskopija
(fluoroquinolone antibiotics; norfloxacin; metal ion complexes; semi-empirical theoretical calculations; 1D- and 2D NMR; homo- and hetero-nuclear 1H and 13 C NMR spectroscopy)

Sažetak
Fluoroquinolones are widely used for treatments of different infectious diseases: urinary, respiratory and bones infections. They are characterized by a broad antibacterial spectrum, good oral absorption and tissue distribution. However, fluoroquinolones show some adverse effects, e.g. complexation with metal cations such as calcium, magnesium, bismuth and aluminium ions, commonly present in antacid and multivitamin preparations. In connection with these the structure of fluoroquinolones at different pH values and the pattern of their complexation is important in studying of drug interactions. We investigated norfloxacin (Figure), orally active fluoroquinolone antimicrobial structurally related to nalidixic acid. The structure of norfloxacin (NF), were investigated by one- and two-dimensional homo- and heteronuclear 1H and 13C NMR spectroscopy and by semi-empirical theoretical calculations. The nuclear shieldings (chemical shifts) were calculated with GIAO/DFT theoretical method. The two-dimensional NMR techniques: COSY, COSYLR, NOESY, ROESY, HMQC and HMBC were used for structural and conformational determination. Complexes with the following metal ions were prepared: Ca2+, Mg2+, Fe2+, Fe3+, Cu2+, Zn2+, Al3+ and the complexation was studied by IR spectra as well. The study revealed fold-in orientation of the side-chain CH3 group and pyperazine ring and the complexation with metal ions at the oxygen atoms of carboxyl and carbonyl groups of NF.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija

Napomena
Rezultati istraživanja objavljeni u radu rezultat su dugogodišnje suradnje Farmaceutsko-biokemijskog fakulteta i NMR centra Instituta Ruđer Bošković, u polju primjene suvremenih spektroskopskih metoda u strukturnoj analizi lijekova i njihovih metabolita, te drugih biološki aktivnih spojeva.

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