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

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

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.

• Jezik: Angleški jezik
• Ključne besede: cyanothiophene scaffold, oil-in-water emulsion, distribution, interfacial concentration, drug-like properties, antioxidant
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FFA - Fakulteta za farmacijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2020
• Št. strani: 16 str.
• Številčenje: Vol. 9, iss. 7, art. 623
• PID: 20.500.12556/RUL-133796
• UDK: 615.4:54:615.015.8
• ISSN pri članku: 2076-3921
• DOI: 10.3390/antiox9070623
• COBISS.SI-ID: 22720003
• Datum objave v RUL: 15.12.2021

Gradivo je del revije

• Naslov: Antioxidants
• Skrajšan naslov: Antioxidants
• Založnik: MDPI
• ISSN: 2076-3921
• COBISS.SI-ID: 522976025

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.
• Začetek licenciranja: 16.07.2020

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: farmacevtska kemija, bakterijska rezistenca

Projekti

• Financer: Drugi - Drug financer ali več financerjev
• Program financ.: University of Vigo, Talent Recruitment

• Financer: ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
• Številka projekta: P1-0208
• Naslov: Farmacevtska kemija: načrtovanje, sinteza in vrednotenje učinkovin