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Molecular Membrane Biology Volume 21, 2004 - Issue 4
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Paper

The hypotensive drug 2-hydroxyoleic acid modifies the structural properties of model membranes

Francisca Barceló Laboratory of Molecular and Cellular Biomedicine, Institut Universitari d'Investigacions en Ciències de la Salut (IUNICS), Associate Unit of the Instituto de la Grasa (CSIC), Departments of Biology and Chemistry, University of the Balearic Islands, Ctra. Valldemossa, Km 7.5, E-07122, Palma de Mallorca, Spain
,
Jesús Prades Laboratory of Molecular and Cellular Biomedicine, Institut Universitari d'Investigacions en Ciències de la Salut (IUNICS), Associate Unit of the Instituto de la Grasa (CSIC), Departments of Biology and Chemistry, University of the Balearic Islands, Ctra. Valldemossa, Km 7.5, E-07122, Palma de Mallorca, Spain
,
Sérgio S. Funari Max-Planck Institute for Colloids and Interfaces, HASYLAB, Notkestrasse 85, D-22603, Hamburg, Germany
,
Juan Frau Laboratory of Molecular and Cellular Biomedicine, Institut Universitari d'Investigacions en Ciències de la Salut (IUNICS), Associate Unit of the Instituto de la Grasa (CSIC), Departments of Biology and Chemistry, University of the Balearic Islands, Ctra. Valldemossa, Km 7.5, E-07122, Palma de Mallorca, Spain
,
Regina Alemany Laboratory of Molecular and Cellular Biomedicine, Institut Universitari d'Investigacions en Ciències de la Salut (IUNICS), Associate Unit of the Instituto de la Grasa (CSIC), Departments of Biology and Chemistry, University of the Balearic Islands, Ctra. Valldemossa, Km 7.5, E-07122, Palma de Mallorca, Spain
&
Pablo V. Escribá Laboratory of Molecular and Cellular Biomedicine, Institut Universitari d'Investigacions en Ciències de la Salut (IUNICS), Associate Unit of the Instituto de la Grasa (CSIC), Departments of Biology and Chemistry, University of the Balearic Islands, Ctra. Valldemossa, Km 7.5, E-07122, Palma de Mallorca, SpainCorrespondence[email protected]
Pages 261-268 | Received 09 Feb 2004, Published online: 09 Jul 2009

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Jesús Prades, Sérgio S. Funari, Manuel Gomez-Florit, Oliver Vögler & Francisca Barceló. (2012) Effect of a 2-hydroxylated fatty acid on Cholesterol-rich membrane domains. Molecular Membrane Biology 29:8, pages 333-343.
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Jesús Prades, Regina Alemany, Javier S. Perona, Sérgio S. Funari, Oliver Vögler, Valentina Ruiz-Gutiérrez, Pablo V. Escribá & Francisca Barceló. (2008) Effects of 2-hydroxyoleic acid on the structural properties of biological and model plasma membranes. Molecular Membrane Biology 25:1, pages 46-57.
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Sérgio S. Funari, Jesús Prades, Pablo V. Escribá & Francisca Barceló. (2005) Farnesol and geranylgeraniol modulate the structural properties of phosphatidylethanolamine model membranes. Molecular Membrane Biology 22:4, pages 303-311.
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Articles from other publishers (40)

Rita Morán-Zendejas & Aldo A. Rodríguez-Menchaca. (2023) The anti-tumor drug 2-hydroxyoleic acid regulates the oncogenic potassium channel Kv10.1. Beni-Suef University Journal of Basic and Applied Sciences 12:1.
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Julia Ortiz, José A. Teruel, Francisco J. Aranda & Antonio Ortiz. (2022) Anticancer drugs tamoxifen and 4hydroxytamoxifen as effectors of phosphatidylethanolamine lipid polymorphism. Chemistry and Physics of Lipids 248, pages 105239.
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Maha Ali Alghamdi, Najwa Mohamad, Faris Mohammed Alsobyan, Khaled Greish & Mohd Cairul Iqbal Mohd Amin. 2022. Polymeric Micelles for Drug Delivery. Polymeric Micelles for Drug Delivery 315 345 .
Ipek Sahin. (2021) Cholecalciferol has strong effect on the order and dynamics of DPPC membranes: A combined Fourier transform infrared spectroscopy and differential scanning calorimetry study. Vibrational Spectroscopy 113, pages 103207.
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Rama Prajapati, Mark Gontsarik, Anan Yaghmur & Stefan Salentinig. (2019) pH-Responsive Nano-Self-Assemblies of the Anticancer Drug 2-Hydroxyoleic Acid. Langmuir 35:24, pages 7954-7961.
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Ediz Sariisik, Mustafa Koçak, Fatma Kucuk Baloglu & Feride Severcan. (2019) Interaction of the cholesterol reducing agent simvastatin with zwitterionic DPPC and charged DPPG phospholipid membranes. Biochimica et Biophysica Acta (BBA) - Biomembranes 1861:4, pages 810-818.
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Joaquim Trigo Marquês, H. Susana Marinho & Rodrigo F.M. de Almeida. (2018) Sphingolipid hydroxylation in mammals, yeast and plants – An integrated view. Progress in Lipid Research 71, pages 18-42.
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Pablo V. Escribá. (2017) Membrane-lipid therapy: A historical perspective of membrane-targeted therapies — From lipid bilayer structure to the pathophysiological regulation of cells. Biochimica et Biophysica Acta (BBA) - Biomembranes 1859:9, pages 1493-1506.
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Stefano Piotto, Lucia Sessa, Pio Iannelli & Simona Concilio. (2017) Computational study on human sphingomyelin synthase 1 (hSMS1). Biochimica et Biophysica Acta (BBA) - Biomembranes 1859:9, pages 1517-1525.
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Pablo V. Escribá. (2017) WITHDRAWN: Membrane-lipid therapy: A historical perspective of membrane-targeted therapies—From lipid bilayer structure to the pathophysiological regulation of cells. Biochimica et Biophysica Acta (BBA) - Biomembranes.
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G.K. Varshney, S.R. Kintali, P.K. Gupta & K. Das. (2017) A comparative study on the effect of Curcumin and Chlorin-p on the transport of the LDS cation across a negatively charged POPG bilayer: Effect of pH. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 173, pages 132-138.
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Vinod Labhasetwar. 2016. Drug Delivery Across Physiological Barriers. Drug Delivery Across Physiological Barriers 271 290 .
Günther H. Peters, Mikkel Werge, Maria Northved Elf-Lind, Jesper J. Madsen, Gustavo F. Velardez & Peter Westh. (2014) Interaction of neurotransmitters with a phospholipid bilayer: A molecular dynamics study. Chemistry and Physics of Lipids 184, pages 7-17.
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R.K. Saini, G.K. Varshney, A. Dube, P.K. Gupta & K. Das. (2014) A comparative study on the effect of Curcumin and Chlorin-p6 on the diffusion of two organic cations across a negatively charged lipid bilayer probed by second harmonic spectroscopy. Journal of Molecular Structure 1074, pages 22-26.
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Victoria Lladó, David J. López, Maitane Ibarguren, María Alonso, Joan B. Soriano, Pablo V. Escribá & Xavier Busquets. (2014) Regulation of the cancer cell membrane lipid composition by NaCHOleate. Biochimica et Biophysica Acta (BBA) - Biomembranes 1838:6, pages 1619-1627.
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Stefano Piotto, Alfonso Trapani, Erminia Bianchino, Maitane Ibarguren, David J. López, Xavier Busquets & Simona Concilio. (2014) The effect of hydroxylated fatty acid-containing phospholipids in the remodeling of lipid membranes. Biochimica et Biophysica Acta (BBA) - Biomembranes 1838:6, pages 1509-1517.
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Stefano Piotto, Simona Concilio, Erminia Bianchino, Pio Iannelli, David J. López, Silvia Terés, Maitane Ibarguren, Gwendolyn Barceló-Coblijn, Maria Laura Martin, Francisca Guardiola-Serrano, María Alonso-Sande, Sérgio S. Funari, Xavier Busquets & Pablo V. Escribá. (2014) Differential effect of 2-hydroxyoleic acid enantiomers on protein (sphingomyelin synthase) and lipid (membrane) targets. Biochimica et Biophysica Acta (BBA) - Biomembranes 1838:6, pages 1628-1637.
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Maitane Ibarguren, David J. López & Pablo V. Escribá. (2014) The effect of natural and synthetic fatty acids on membrane structure, microdomain organization, cellular functions and human health. Biochimica et Biophysica Acta (BBA) - Biomembranes 1838:6, pages 1518-1528.
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Maitane Ibarguren, David J. López, José A. Encinar, José M. González-Ros, Xavier Busquets & Pablo V. Escribá. (2013) Partitioning of liquid-ordered/liquid-disordered membrane microdomains induced by the fluidifying effect of 2-hydroxylated fatty acid derivatives. Biochimica et Biophysica Acta (BBA) - Biomembranes 1828:11, pages 2553-2563.
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Maria Laura Martin, Gerhard Liebisch, Stefan Lehneis, Gerd Schmitz, María Alonso-Sande, Joan Bestard-Escalas, Daniel H. Lopez, José Manuel García-Verdugo, Mario Soriano-Navarro, Xavier Busquets, Pablo V. Escribá & Gwendolyn Barceló-Coblijn. (2013) Sustained activation of sphingomyelin synthase by 2-hydroxyoleic acid induces sphingolipidosis in tumor cells. Journal of Lipid Research 54:5, pages 1457-1465.
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Maria Laura Martin, Gwendolyn Barceló-Coblijn, Rodrigo F.M. de Almeida, Maria Antònia Noguera-Salvà, Silvia Terés, Mónica Higuera, Gerhard Liebisch, Gerd Schmitz, Xavier Busquets & Pablo V. Escribá. (2013) The role of membrane fatty acid remodeling in the antitumor mechanism of action of 2-hydroxyoleic acid. Biochimica et Biophysica Acta (BBA) - Biomembranes 1828:5, pages 1405-1413.
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Vedagopuram Sreekanth & Avinash Bajaj. (2013) Fluorescence (Fluidity/Hydration) and Calorimetric Studies of Interactions of Bile Acid–Drug Conjugates with Model Membranes. The Journal of Physical Chemistry B 117:7, pages 2123-2133.
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Anan Yaghmur, Barbara Sartori & Michael Rappolt. (2012) Self-Assembled Nanostructures of Fully Hydrated Monoelaidin–Elaidic Acid and Monoelaidin–Oleic Acid Systems. Langmuir 28:26, pages 10105-10119.
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Silvia TerésVictoria LladóMónica HigueraGwendolyn Barceló-CoblijnMaria Laura MartinMaria Antònia Noguera-SalvàAmaia Marcilla-EtxenikeJosé Manuel García-Verdugo, Mario Soriano-Navarro, Carlos SausUlises Gómez-Pinedo, Xavier BusquetsPablo V. Escribá. (2012) 2-Hydroxyoleate, a nontoxic membrane binding anticancer drug, induces glioma cell differentiation and autophagy. Proceedings of the National Academy of Sciences 109:22, pages 8489-8494.
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Gwendolyn Barceló-CoblijnMaria Laura MartinRodrigo F. M. de AlmeidaMaria Antònia Noguera-SalvàAmaia Marcilla-EtxenikeFrancisca Guardiola-SerranoAnja Lüth, Burhard Kleuser, John E. Halver & Pablo V. Escribá. (2011) Sphingomyelin and sphingomyelin synthase (SMS) in the malignant transformation of glioma cells and in 2-hydroxyoleic acid therapy. Proceedings of the National Academy of Sciences 108:49, pages 19569-19574.
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Javier Cerezo, José Zúñiga, Adolfo Bastida, Alberto Requena & José Pedro Cerón-Carrasco. (2011) Atomistic Molecular Dynamics Simulations of the Interactions of Oleic and 2-Hydroxyoleic Acids with Phosphatidylcholine Bilayers. The Journal of Physical Chemistry B 115:40, pages 11727-11738.
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Arnau Cordomí, Jesús Prades, Juan Frau, Oliver Vögler, Sérgio S. Funari, Juan J. Perez, Pablo V. Escribá & Francisca Barceló. (2010) Interactions of fatty acids with phosphatidylethanolamine membranes: X-ray diffraction and molecular dynamics studies. Journal of Lipid Research 51:5, pages 1113-1124.
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Chiranjeevi Peetla, Andrew Stine & Vinod Labhasetwar. (2009) Biophysical Interactions with Model Lipid Membranes: Applications in Drug Discovery and Drug Delivery. Molecular Pharmaceutics 6:5, pages 1264-1276.
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Victoria Lladó, Silvia Terés, Mónica Higuera, Rafael Álvarez, Maria Antònia Noguera-Salva, John E. Halver, Pablo V. Escribá & Xavier Busquets. (2009) Pivotal role of dihydrofolate reductase knockdown in the anticancer activity of 2-hydroxyoleic acid. Proceedings of the National Academy of Sciences 106:33, pages 13754-13758.
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Ramona Jenske & Walter Vetter. (2009) Concentrations of medium-chain 2- and 3-hydroxy fatty acids in foodstuffs. Food Chemistry 114:3, pages 1122-1129.
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S. TerésG. Barceló-CoblijnM. BenetR. ÁlvarezR. Bressani, J. E. Halver & P. V. Escribá. (2008) Oleic acid content is responsible for the reduction in blood pressure induced by olive oil. Proceedings of the National Academy of Sciences 105:37, pages 13811-13816.
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Ramona Jenske, Fredrick Lindström, Gerhard Gröbner & Walter Vetter. (2008) Impact of free hydroxylated and methyl-branched fatty acids on the organization of lipid membranes. Chemistry and Physics of Lipids 154:1, pages 26-32.
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Gudrun H. Borchert, Mike Giggey, Frantisek Kolar, Tak Ming Wong, Peter H. Backx & Pablo V. Escriba. (2008) 2-Hydroxyoleic acid affects cardiomyocyte [Ca 2+ ] i transient and contractility in a region-dependent manner . American Journal of Physiology-Heart and Circulatory Physiology 294:4, pages H1948-H1955.
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Jesús Prades, Javier S. Perona, Sérgio S. Funari, Valentina Ruiz-Gutierrez, Pablo V. Escribá & Francisca Barcelo. (2007) Effects of fatty acids on the structural properties of biological and model membranes. Chemistry and Physics of Lipids 149, pages S39.
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Jingzhong Zhang, Theresa Hadlock, Alison Gent & Gary R. Strichartz. (2007) Tetracaine-Membrane Interactions: Effects of Lipid Composition and Phase on Drug Partitioning, Location, and Ionization. Biophysical Journal 92:11, pages 3988-4001.
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Pablo V. Escribá. (2006) Membrane-lipid therapy: a new approach in molecular medicine. Trends in Molecular Medicine 12:1, pages 34-43.
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Jordi Martínez, Antonio Gutiérrez, Jesús Casas, Victoria Lladó, Alicia López-Bellan, Joan Besalduch, Ana Dopazo & Pablo V. Escribá. (2005) The Repression of E2F-1 Is Critical for the Activity of Minerval against Cancer. Journal of Pharmacology and Experimental Therapeutics 315:1, pages 466-474.
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Làszló Vigh, Pablo V. Escribá, Alois Sonnleitner, Max Sonnleitner, Stefano Piotto, Bruno Maresca, Ibolya Horváth & John L. Harwood. (2005) The significance of lipid composition for membrane activity: New concepts and ways of assessing function. Progress in Lipid Research 44:5, pages 303-344.
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Qing Yang, Regina Alemany, Jesús Casas, Klára Kitajka, Stephen M. Lanier & Pablo V. Escribá. (2005) Influence of the Membrane Lipid Structure on Signal Processing via G Protein-Coupled Receptors. Molecular Pharmacology 68:1, pages 210-217.
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Jordi Martínez, Oliver Vögler, Jesús Casas, Francisca Barceló, Regina Alemany, Jesús Prades, Tünde Nagy, Carmela Baamonde, Philip G. Kasprzyk, Silvia Terés, Carlos Saus & Pablo V. Escribá. (2005) Membrane Structure Modulation, Protein Kinase Cα Activation, and Anticancer Activity of Minerval. Molecular Pharmacology 67:2, pages 531-540.
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