RESUMO
Novel quinoline derivatives were synthesized based on 6-amino-substituted quinoline, and antioxidant activity of these compounds is studied by p-nitroso-N,N-dimethylaniline assay. The rate of the reaction between OH radicals and quinoline derivatives is determined by photometric method and the obtained results are compared with that of well-known antioxidant vitamin C. Quinoline derivatives exhibit pronounced antioxidant activity, which strongly depends on the structural features of compounds. Photophysical properties such as UV-Vis absorption and fluorescence maxima, and Stokes shift are also reported. To reveal the potential application of novel quinoline derivatives as fluorescence probes the values of quantum yields are determined and the obtained results are explained in terms of structural features of compounds.
RESUMO
Binding of 2-(5-mercapto-1,3,4-oxadiazol-2-yl)-6-methylquinolin-4-ol (C1), a biologically active substance, to bovine blood plasma albumin (BSA) at 293, 298, and 303 K was studied using fluorescence (steady state, synchronous, excitation/emission matrix) and FT-IR spectroscopy methods. The experimental results showed that C1 causes fluorescence quenching of BSA through both static and dynamic quenching mechanisms. The thermodynamic parameters, enthalpy and entropy change, for the static quenching were calculated to be - 35.73 kJ mol-1 and - 35.34 J mol-1 K-1, which indicated that hydrogen bonding and van der Waals interactions were the predominant intermolecular forces regulating C1-BSA interactions. Distance between donor and acceptor (2.14, 2.26, and 2.30 nm) depending on the temperature, obtained from intrinsic Förster resonance energy transfer calculations, revealed the static quenching mechanism of BSA fluorescence in 0-3.0 × 10-5 mol/dm3 concentration range of C1. The micro-environmental and conformational changes in BSA structure, established by synchronous, excitation/emission matrices and FT-IR spectra showed the changes in the BSA secondary structure.
