Eczacılık Fakültesi / Faculty of Pharmacy

Permanent URI for this collectionhttps://hdl.handle.net/11727/5700

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Author: search.filters.author.Gunduz, Miyase Gozde

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    Azole Rings Linked To Cox Inhibitors Via Hydrazone Bridge: Synthesis, Stereochemical Analysis, And Investigation Of Antimicrobial Activity
    (Başkent Üniversitesi Eczacılık Fakültesi, 2024-04-19) Karaguzel, Ayse; Ugur, Suemeyye Buran; Cetinkaya, Yasin; Dogan, Senguel Dilem; Stevanovic, Milena; Nikodinovic-Runic, Jasmina; Gunduz, Miyase Gozde
    Nonsteroidal anti-inflammatory drugs (NSAIDs) alleviate inflammation and pain through the inhibition of cyclooxygenase (COX) enzymes. Besides these widely recognized therapeutic utilizations, NSAIDs have been reported to display moderate antimicrobial activity and enhance antimicrobial efficacy when administered in combination with commercial antimicrobial drugs. In the present study, we designed novel potential antimicrobial agents by linking some NSAIDs (ibuprofen, flurbiprofen, and naproxen) to various azole rings (pyrazole, imidazole, triazole, and benzimidazole) via hydrazone functionality. The hydrazone linker was introduced into the chemical scaffold of the title molecules by the reaction between hydrazides obtained from NSAIDs and inhouse synthesized azole-carrying benzaldehydes. The structures of the target compounds were elucidated by a combination of spectral methods. The NOESY spectra and stereochemical analyses performed using DFT method confirmed the presence of the target molecules as a mixture of E(C=N)-E(N-N)-synperiplanar and E(C=N)-E(N-N)antiperiplanar conformers in DMSO-d6 solution. 1H and 13C NMR chemical shift values in DMSO were calculated using the GIAO method and compared with the experimental NMR data. Finally, some derivatives were demonstrated to inhibit Candida albicans filamentation and/or bacterial communication system known as quorum sensing. For COX inhibitor-azole hybrids with antimicrobial potency, naproxen appeared to be the most appropriate NSAID, while bulky benzimidazole was not found as a preferable azole ring.
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    Theoretical and experimental investigation of 1,4-dihydropyridine-based hexahydroquinoline-3-carboxylates: Photophysics and bovine serum albumin binding studies
    (2022) da Luz, Lilian Camargo; Gunduz, Miyase Gozde; Beal, Roiney; Zanotto, Gabriel Modernell; Kuhn, Eduardo Ramires; Netz, Paulo Augusto; Safak, Cihat; Bruno Goncalves, Paulo Fernando; Santos, Fabiano da Silveira; Rodembusch, Fabiano Severo
    In this article, the binding affinity of 1,4-dihydropyridine-based hexahydroquinoline-3-carboxylates with bovine serum albumin (BSA) was studied by electronic spectroscopies, quantum calculations, and molecular docking. These compounds were obtained by the one-pot microwave-assisted method via a modified Hantzsch reaction. The photophysical characterization showed in organic solutions absorption maxima in the UV region, ascribed to spin and symmetry allowed electronic transitions (1)pi-pi*. In addition, they presented a main fluorescence emission in the violet-blue regions (406-445 nm), with a relatively large Stokes shift (54-81 nm), depending on the structure of the compounds. BSA fluorescence quenching experiments based on the intrinsic fluorescence of the Trp residues were successfully applied to these compounds, indicating strong interaction with BSA by a static mechanism. The docking simulations corroborated the strong interaction between the studied compounds and BSA, where the surroundings of Trp213 seemed to be the preferred interaction site for all compounds and were responsible for the fluorescence quenching effects.