Encyclopedia of Cancer

Living Edition
| Editors: Manfred Schwab

2-Hydroxyoleic Acid

  • Maitane Ibarguren
  • Paula Fernández-García
  • Laura Arbona
  • Xavier Busquets
  • Pablo V. Escribá
Living reference work entry
DOI: https://doi.org/10.1007/978-3-642-27841-9_2898-2

Synonyms

Definition

2-Hydroxyoleic acid (2OHOA) is a first-in-class Membrane-Lipid Therapy anticancer drug that specifically activates sphingomyelin (SM) synthase (SMS), a new therapeutic target in the fight against cancer. SMS activation by 2OHOA causes profound membrane lipid remodeling in cancer cells but not in normal cells, altering the organization of membrane microdomains. Normalization of the lipid composition/structure of cancer cell membranes provokes changes in the type and abundance of extrinsic membrane proteins that receive and propagate cell signals. These regulatory effects induce cell cycle arrest, cell differentiation, and programmed cell death of cancer cells.

Characteristics

Structure

2OHOA has 18 C atoms with a cis double bond between carbons 9 and 10 (Fig. 1). It is classified as a monounsaturated omega-9 fatty acid, abbreviated as 18:1n-9 or 18:1 cis9. It has a hydroxyl moiety on the α-carbon that prevents its rapid...

Keywords

Glioma Cell Endoplasmic Reticulum Stress Autophagic Cell Death Synthetic Fatty Acid Cancer Cell Membrane 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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References

  1. Barceló-Coblijn G, Martin ML, de Almeida RF, Noguera-Salva MA, Marcilla-Etxenike A, Guardiola-Serrano F, Luth A, Kleuser B, Halver JE, Escribá PV (2011) Sphingomyelin and sphingomyelin synthase (SMS) in the malignant transformation of glioma cells and in 2-hydroxyoleic acid therapy. Proc Natl Acad Sci 108:19569–19574PubMedCentralCrossRefPubMedGoogle Scholar
  2. Ibarguren M, López DJ, Escribá PV (2014) The effect of natural and synthetic fatty acids on membrane structure, microdomain organization, cellular functions and human health. Biochim Biophys Acta 1838:1518–1528CrossRefPubMedGoogle Scholar
  3. Lladó V, Gutiérrez A, Martínez J, Casas J, Terés S, Higuera M, Galmés A, Saus C, Besalduch J, Busquets X, Escribá PV (2010) Minerval induces apoptosis in Jurkat and other cancer cells. J Cell Mol Med 14:659–670PubMedCentralPubMedGoogle Scholar
  4. Marcilla-Etxenike A, Martín ML, Noguera-Salvà MA, García-Verdugo JM, Soriano-Navarro M, Dey I, Escribá PV, Busquets X (2012) 2-Hydroxyoleic acid induces ER stress and autophagy in various human glioma cell lines. PLoS One 7(10):e48235PubMedCentralCrossRefPubMedGoogle Scholar
  5. Terés S, Lladó V, Higuera M, Barceló-Coblijn G, Martin ML, Noguera-Salva MA, Marcilla-Etxenike A, García-Verdugo JM, Soriano-Navarro M, Saus C, Gómez-Pinedo U, Busquets X, Escribá PV (2012) 2-Hydroxyoleate, a nontoxic membrane binding anticancer drug, induces glioma cell differentiation and autophagy. Proc Natl Acad Sci U S A 109:8489–8494PubMedCentralCrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  • Maitane Ibarguren
    • 1
  • Paula Fernández-García
    • 1
  • Laura Arbona
    • 1
  • Xavier Busquets
    • 1
  • Pablo V. Escribá
    • 1
  1. 1.Department of BiologyUniversity of the Balearic IslandsPalma de MallorcaSpain