20.500.12556/RUL-133796 Synthesis, in vitro antioxidant properties and distribution of a new cyanothiophene-based phenolic compound in olive oil-in-water emulsions We synthesized and determined the antioxidant activity and distribution of a new cyanothiophene-based compound, N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-3,5-dihydroxybenzamide (SIM-53B), in intact stripped olive oil-in-water emulsion. The in vitro antioxidant properties of SIM-53B were evaluated and compared to those for Trolox and resveratrol. Addition of an emulsifier (Tween 20) creates a narrow region, the aqueous–oil interface, and the distribution of SIM-53B can be described by two partition constants: P$_W$$^I$ (between aqueous/interfacial regions) and P$_O$$^I$ (between oil/interfacial regions). The effects of emulsifier concentration expressed in terms of the volume fraction, Φ$_I$, and O/W ratio were also evaluated on its distribution. SIM-53B is predominantly distributed (>90%) in the interfacial region of 1:9 (O/W) olive oil-in-water emulsions at the lowest emulsifier volume fraction (Φ$_I$ = 0.005) and only a small fraction is located in the aqueous (<5%) and the oil (<5%) regions. Besides, the concentration of SIM-53B in the interfacial region of the emulsions is ~170–190-fold higher than the stoichiometric concentration, emphasizing the compartmentalization effects. Results suggest that the emulsifier volume fraction is a key parameter that may modulate significantly its concentration in the interface. Our study suggests that cyanothiophene-based compounds may be interesting additives for potential lipid protection in biomembranes or other lipid-based systems. cyanothiophene scaffold oil-in-water emulsion distribution interfacial concentration drug-like properties antioxidant farmacevtska kemija bakterijska rezistenca true false true Angleški jezik Slovenski jezik Članek v reviji 2021-12-15 12:35:43 2021-12-15 12:35:47 2022-09-13 03:52:41 0000-00-00 00:00:00 2020 0 0 16 str. iss. 7, art. 623 Vol. 9 June 2020 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 615.4:54:615.015.8 2076-3921 10.3390/antiox9070623 22720003 RAZ_Losada-Barreiro_Sonia_2020.pdf RAZ_Losada-Barreiro_Sonia_2020.pdf 1 E260AD1BE95AECE17038C24AC704A114 83a12cdcd350bb96bbce72ac0299d8b57018dabccd2464d4581388c5109e0366 5e4d5934-5d9b-11ec-abdb-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=152140 https://www.mdpi.com/2076-3921/9/7/623 0 1688d534-5d9b-11ec-abdb-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=152139 Fakulteta za farmacijo 0 0 0