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

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

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.

• Language: English
• Keywords: cyanothiophene scaffold, oil-in-water emulsion, distribution, interfacial concentration, drug-like properties, antioxidant
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FFA - Faculty of Pharmacy
• Publication status: Published
• Publication version: Version of Record
• Year: 2020
• Number of pages: 16 str.
• Numbering: Vol. 9, iss. 7, art. 623
• PID: 20.500.12556/RUL-133796
• UDC: 615.4:54:615.015.8
• ISSN on article: 2076-3921
• DOI: 10.3390/antiox9070623
• COBISS.SI-ID: 22720003
• Publication date in RUL: 15.12.2021

LOSADA-BARREIRO, Sonia, SOVA, Matej, MRAVLJAK, Janez, SASO, Luciano and BRAVO-DÍAZ, Carlos, 2020, Synthesis, in vitro antioxidant properties and distribution of a new cyanothiophene-based phenolic compound in olive oil-in-water emulsions. Antioxidants [online]. 2020. Vol. 9, no. 7,  623. [Accessed 26 July 2025]. DOI 10.3390/antiox9070623. Retrieved from: https://repozitorij.uni-lj.si/IzpisGradiva.php?lang=eng&id=133796

Record is a part of a journal

• Title: Antioxidants
• Publisher: MDPI
• ISSN: 2076-3921
• COBISS.SI-ID: 522976025

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
• Licensing start date: 16.07.2020

Secondary language

• Language: Slovenian
• Keywords: farmacevtska kemija, bakterijska rezistenca

Projects

• Funder: Other - Other funder or multiple funders
• Funding programme: University of Vigo, Talent Recruitment

• Funder: ARRS - Slovenian Research Agency
• Project number: P1-0208
• Name: Farmacevtska kemija: načrtovanje, sinteza in vrednotenje učinkovin