Development of novel sophorolipids with improved cytotoxic activity toward MDA-MB-231 breast cancer cells

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...

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Bibliographic Details
Published in:Journal of molecular recognition 2015-03, Vol.28 (3), p.155-165
Main 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
Format: Article
Language:English
Subjects:
Antineoplastic Agents - metabolism
Antineoplastic Agents - pharmacology
Breast
breast cancer
Breast Neoplasms - drug therapy
Cancer
Cell Line, Tumor
Cell Movement - drug effects
Chromatography, Liquid - methods
Culture Media - chemistry
cytotoxicity
Female
gamma-Linolenic Acid - pharmacology
Glycolipids - biosynthesis
Glycolipids - pharmacology
Humans
Ionization
Liquid chromatography
Mass spectrometry
MDA-MB-231 cells
Media
Micelles
Migration
Plant Oils - pharmacology
Reactive Oxygen Species - metabolism
Saccharomycetales - physiology
sophorolipid
Spectrometry, Mass, Electrospray Ionization
Starmerella bombicola
surface tension
Tandem Mass Spectrometry
Viability
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Summary: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 Starmerella bombicola 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 (γCMC) 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. Sophorolipids (SLs) biosynthesized by Starmerella bombicola, in a media supplemented with borage oil, improved cytotoxic activity against MDA‐MB‐231 breast cancer cells. The diacetylated lactonic SLs, C18:0, C18:1, C18:2, and C18:3, were isolated and purified. An increase in critical micelle concentration (CMC) and γCMC were observed with the number of double bonds of lactonic SLs. High cytotoxic effect against MDA‐MB‐231 cells was observed with C18:0 and C18:1 and, for the first time, C18:3. C18:1 was able to inhibit MDA‐MB‐231 cell migration without compromising cell viability.
ISSN:0952-3499
1099-1352
DOI:10.1002/jmr.2403