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

J Mol Recognit. 2015 Mar;28(3):155-65. doi: 10.1002/jmr.2403. Epub 2015 Feb 3.

Abstract

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.

Keywords: MDA-MB-231 cells; Starmerella bombicola; breast cancer; cytotoxicity; sophorolipid; surface tension.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / metabolism*
  • Antineoplastic Agents / pharmacology*
  • Breast Neoplasms / drug therapy*
  • Cell Line, Tumor
  • Cell Movement / drug effects
  • Chromatography, Liquid / methods
  • Culture Media / chemistry
  • Female
  • Glycolipids / biosynthesis*
  • Glycolipids / pharmacology*
  • Humans
  • Plant Oils / pharmacology
  • Reactive Oxygen Species / metabolism
  • Saccharomycetales / physiology*
  • Spectrometry, Mass, Electrospray Ionization
  • Tandem Mass Spectrometry
  • gamma-Linolenic Acid / pharmacology

Substances

  • Antineoplastic Agents
  • Culture Media
  • Glycolipids
  • Plant Oils
  • Reactive Oxygen Species
  • gamma-Linolenic Acid
  • borage oil