Synthesis, in vitro antioxidant properties and distribution of a new cyanothiophene-based phenolic compound in olive oil-In-water emulsions

Sonia Losada-Barreiro (Avtor), Matej Sova (Avtor), Janez Mravljak (Avtor), Luciano Saso (Avtor), Carlos Bravo-Díaz (Avtor)

Povzetek

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: PWI (between aqueous/interfacial regions) and POI (between oil/interfacial regions). The effects of emulsifier concentration expressed in terms of the volume fraction, [fi]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 ([fi]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.

Ključne besede

cyanothiophene scaffold;oil-in-water emulsion;distribution;interfacial concentration;drug-like properties;antioxidant;

Podatki

Jezik:	Angleški jezik
Leto izida:	2020
Tipologija:	1.01 - Izvirni znanstveni članek
Organizacija:	UL FFA - Fakulteta za farmacijo
UDK:	615.4:54:615.015.8
COBISS:	22720003
ISSN:	2076-3921
Št. ogledov:	210
Št. prenosov:	58
Ocena:	0 (0 glasov)
Metapodatki:

Ostali podatki

Sekundarni jezik:	Slovenski jezik
Sekundarne ključne besede:	Farmacevtska kemija;Bakterijska rezistenca;
Vrsta dela (COBISS):	Članek v reviji
Strani:	str. 1-16
Letnik:	ǂVol. ǂ9
Zvezek:	ǂiss. ǂ7
Čas izdaje:	June 2020
DOI:	10.3390/antiox9070623
ID:	14101875