title: Development of novel sophorolipids with improved cytotoxic activity toward MDA-MB-231 breast cancer cells.
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.
authors: Faculdade Farmácia, Universidade Lisboa, Av. Prof. Gama Pinto, 1649-003, Lisboa, Portugal; Instituto Investigação do Medicamento (iMed.ULisboa), Faculdade Farmácia, Universidade Lisboa, Av. Prof. Gama Pinto, 1649-003, Lisboa, Portugal.
authors: Isabel A C
authors: IA
authors: Ribeiro
authors: Célia M C
authors: CM
authors: Faustino
authors: Patrícia S
authors: PS
authors: Guerreiro
authors: Raquel F M
authors: RF
authors: Frade
authors: M Rosário
authors: MR
authors: Bronze
authors: Matilde F
authors: MF
authors: Castro
authors: Maria H L
authors: MH
authors: Ribeiro
mesh_terms: D000970:Antineoplastic Agents / Q000378:metabolism* / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000188:drug therapy*; D045744:Cell Line, Tumor; D002465:Cell Movement / Q000187:drug effects; D002853:Chromatography, Liquid / Q000379:methods; D003470:Culture Media / Q000737:chemistry; D005260:Female; D006017:Glycolipids / Q000096:biosynthesis* / Q000494:pharmacology*; D006801:Humans; D010938:Plant Oils / Q000494:pharmacology; D017382:Reactive Oxygen Species / Q000378:metabolism; D004718:Saccharomycetales / Q000502:physiology*; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry; D017965:gamma-Linolenic Acid / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D003470:Culture Media; D006017:Glycolipids; D010938:Plant Oils; D017382:Reactive Oxygen Species; D017965:gamma-Linolenic Acid; C079363:borage oil
keywords: MDA-MB-231 cells; Starmerella bombicola; breast cancer; cytotoxicity; sophorolipid; surface tension