20.500.12556/RUL-131852 Acetylcholinesterase inhibition and antioxidant activity of N-trans-caffeoyldopamine and N-trans-feruloyldopamine Phenolic acids and their derivatives found in nature are well-known for their potential biological activity. In this study, two amides derived from trans-caffeic/ferulic acid and dopamine were synthesized and characterized by Fourier-transform infrared spectroscopy (FTIR), mass spectrometry, proton and carbon-13 nuclear magnetic resonance spectroscopy. The compounds were tested for the inhibition of acetylcholinesterase (AChE) from Electrophorus electricus and for antioxidant activity by scavenging 2,2-diphenyl-1-pycrylhydrazyl free radical (DPPH$^•$) and 2,2′-azinobis(3-ethylbenzothiazoline-6-sulphonic acid) radical cation (ABTS$^{•+}$), reducing ferric ions, and ferrous ions chelation. N-trans-Feruloyldopamine displayed the highest inhibitory effect on AChE with half-maximal inhibitory concentration (IC$_{50}$) values of 8.52 µM. In addition, an in silico study was done to determine the most favorable AChE cluster with the synthesized compounds. Further, these clusters were investigated for binding positions at the lowest free binding energy. Both synthesized hydroxycinnamates were found to be better antioxidants than the parent acids in in vitro tests applied. N-trans-Caffeoyldopamine showed the best antioxidant activity in the three tested methods—against non-biological stable free radicals IC$_{50}$ 5.95 µM for DPPH$^•$, 0.24 µM for the ABTS$^{•+}$ method, and for reducing power (ascorbic acid equivalent (AAE) 822.45 µmol/mmol)—while for chelation activity against Fe$^{2+}$ ions N-trans-feruloyldopamine had slightly better antioxidant activity (IC$_{50}$ 3.17 mM). acetylcholinesterase inhibition antioxidant activity N-trans-feruloyldopamine N-trans-caffeoyldopamine inhibitorji acetilholinesteraze antioksidativna aktivnost N-trans-feruloildopamin N-trans-kafeoildopamin true false true Angleški jezik Slovenski jezik Članek v reviji 2021-10-04 15:29:04 2021-10-04 15:29:04 2022-09-10 04:14:10 0000-00-00 00:00:00 2018 0 0 12 str. iss. 2, art. 11 Vol. 86 2018 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547.56 0036-8709 10.3390/scipharm86020011 1537763267 RAZ_Dizdar_M._2018.pdf RAZ_Dizdar_M._2018.pdf 1 C54BDCB39FD2917C3EF043D698CBA984 97d1dddb548c873755369b05caec10a7edd6cee1f2272cd388a60489a6011a0c fa4a7f59-2516-11ec-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=149273 http://www.mdpi.com/2218-0532/86/2/11 0 c14e97bf-2516-11ec-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=149272 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0