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@ARTICLE{Piotto:192583,
      author       = {Piotto, Stefano and Concilio, Simona and Bianchino, Erminia
                      and Iannelli, Pio and López, David J. and Terés, Silvia
                      and Ibarguren, Maitane and Barceló-Coblijn, Gwendolyn and
                      Martin, Maria Laura and Guardiola-Serrano, Francisca and
                      Alonso-Sande, María and Funari, Sérgio S. and Busquets,
                      Xavier and Escribá, Pablo V.},
      title        = {{D}ifferential effect of 2-hydroxyoleic acid enantiomers on
                      protein (sphingomyelin synthase) and lipid (membrane)
                      targets},
      journal      = {Biochimica et biophysica acta / Biomembranes},
      volume       = {1838},
      number       = {6},
      issn         = {0005-2736},
      address      = {Amsterdam},
      publisher    = {Elsevier},
      reportid     = {PUBDB-2014-04165},
      pages        = {1628 - 1637},
      year         = {2014},
      abstract     = {The complex dual mechanism of action of 2-hydroxyoleic acid
                      (2OHOA), a potent anti-tumor compound used in membrane lipid
                      therapy (MLT), has yet to be fully elucidated. It has been
                      demonstrated that 2OHOA increases the sphingomyelin (SM)
                      cell content via SM synthase (SGMS) activation. Its presence
                      in membranes provokes changes in the membrane lipid
                      structure that induce the translocation of PKC to the
                      membrane and the subsequent overexpression of CDK inhibitor
                      proteins (e.g., p21(Cip1)). In addition, 2OHOA also induces
                      the translocation of Ras to the cytoplasm, provoking the
                      silencing of MAPK and its related pathways. These two
                      differential modes of action are triggered by the
                      interactions of 2OHOA with either lipids or proteins. To
                      investigate the molecular basis of the different
                      interactions of 2OHOA with membrane lipids and proteins, we
                      synthesized the R and S enantiomers of this compound. A
                      molecular dynamics study indicated that both enantiomers
                      interact similarly with lipid bilayers, which was further
                      confirmed by X-ray diffraction studies. By contrast, only
                      the S enantiomer was able to activate SMS in human glioma
                      U118 cells. Moreover, the anti-tumor efficacy of the S
                      enantiomer was greater than that of the R enantiomer, as the
                      former can act through both MLT mechanisms. The present
                      study provides additional information on this novel
                      therapeutic approach and on the magnitude of the therapeutic
                      effects of type-1 and type-2 MLT approaches. This article is
                      part of a Special Issue entitled: Membrane Structure and
                      Function: Relevance in the Cell's Physiology, Pathology and
                      Therapy.},
      cin          = {DOOR},
      ddc          = {570},
      cid          = {I:(DE-H253)HAS-User-20120731},
      pnm          = {DORIS Beamline A2 (POF2-54G13) / FS-Proposal: I-20110036 EC
                      (I-20110036-EC) / FS-Proposal: I-20110620 EC
                      (I-20110620-EC)},
      pid          = {G:(DE-H253)POF2-A2-20130405 / G:(DE-H253)I-20110036-EC /
                      G:(DE-H253)I-20110620-EC},
      experiment   = {EXP:(DE-H253)D-A2-20150101},
      typ          = {PUB:(DE-HGF)16},
      UT           = {WOS:000335619200017},
      pubmed       = {pmid:24412218},
      doi          = {10.1016/j.bbamem.2013.12.023},
      url          = {https://bib-pubdb1.desy.de/record/192583},
}