Development of novel sophorolipids with improved cytotoxic activity toward MDA‐MB‐231 breast cancer cells1. Issue 3 (3rd February 2015)

• Record Type: Journal Article
• Authors: Ribeiro, Isabel A. C.; Faustino, Célia M. C.; Guerreiro, Patrícia S.; Frade, Raquel F. M.; Bronze, M. Rosário; Castro, Matilde F.; Ribeiro, Maria H. L; Fleminger, Gideon; Jungbauer, Alois
• Is Part Of: Journal of molecular recognition. Volume 28:Issue 3(2015:Mar.)
• Page Start: 155
• Page End: 165
• Publication Date: 2015-02-03
• Subjects: Molecular recognition -- Periodicals; Models, Molecular -- Periodicals; Molecular Conformation -- Periodicals; Molecular Sequence Data -- Periodicals; Molecular Structure -- Periodicals; Carrier Proteins -- Periodicals; 572.8
• DOI: 10.1002/jmr.2403
• Languages: English
• ISSNs: 0952-3499

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Sophorolipids (SLs) are glycolipid biosurfactants, produced as a mixture of several compounds by some nonpathogenic yeast. In the current study, separation of individual SLs from mixtures with further evaluation of their surface properties and biologic activity on MDA‐MB‐321 breast cancer cell line were investigated. SLs were biosynthesized by <italic>Starmerella bombicola</italic> in a culture media supplemented with borage oil. A reverse‐phase flash chromatography method with an automated system coupled with a prepacked cartridge was used to separate and purify the main SLs. Compositional analysis of SLs was performed by high‐performance liquid chromatography with electrospray ionization mass spectrometry and tandem mass spectrometry. The following diacetylated lactonic SLs were isolated and purified: C18:0, C18:1, C18:2, and C18:3. The critical micelle concentration (CMC) and surface tension at CMC (<italic>γ</italic><sub>CMC</sub>) of the purified SLs showed an increase with the number of double bonds. High cytotoxic effect against MDA‐MB‐231 cells was observed with C18:0 and C18:1 lactonic SLs. The cytotoxic effects of C18:3 lactonic SL on cancerous cells were for the first time studied. This cytotoxic effect was considerably higher than the promoted by acidic SLs; however, it induced a lower effect than the previously mentioned SLs, C18:0 and C18:1. To our knowledge, for the first time, C18:1 lactonic SL, in selected concentrations, proved to be able to inhibit MDA‐MB‐231 cell migration without compromising cell viability and to increase intracellular reactive oxygen species. Copyright © 2015 John Wiley & Sons, Ltd.</p> </abstract>