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Synthesis, in vitro antioxidant properties and distribution of a new cyanothiophene-based phenolic compound in olive oil-in-water emulsions
ID Losada-Barreiro, Sonia (Author), ID Sova, Matej (Author), ID Mravljak, Janez (Author), ID Saso, Luciano (Author), ID Bravo-Díaz, Carlos (Author)

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Abstract
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, ΦI, 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 (ΦI = 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 This link opens in a new window
UDC:615.4:54:615.015.8
ISSN on article:2076-3921
DOI:10.3390/antiox9070623 This link opens in a new window
COBISS.SI-ID:22720003 This link opens in a new window
Publication date in RUL:15.12.2021
Views:1262
Downloads:175
Metadata:XML DC-XML DC-RDF
:
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 8 July 2025]. DOI 10.3390/antiox9070623. Retrieved from: https://repozitorij.uni-lj.si/IzpisGradiva.php?lang=eng&id=133796
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Record is a part of a journal

Title:Antioxidants
Publisher:MDPI
ISSN:2076-3921
COBISS.SI-ID:522976025 This link opens in a new window

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

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