Home LiteratureArticle Details
PMID: 16581831 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't

Characterization of two oxidatively modified phospholipids in mixed monolayers with DPPC.

Biophysical journal ·Vol. 90 ·No. 12 ·2006-06-15 ·Pages 4488-99

Sabatini K, Mattila JP, Megli FM, Kinnunen PK

Abstract

The properties of two oxidatively modified phospholipids viz. 1-palmitoyl-2-(9'-oxo-nonanoyl)-sn-glycero-3-phosphocholine (PoxnoPC) and 1-palmitoyl-2-azelaoyl-sn-glycero-3-phosphocholine (PazePC), were investigated using a Langmuir balance, recording force-area (pi-A) isotherms and surface potential psi. In mixed monolayers with 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) a progressive disappearance of the liquid expanded-liquid condensed transition and film expansion was observed with increasing content of the oxidized phospholipids. The above is in agreement with fluorescence microscopy of the monolayers, which revealed an increase in the liquid expanded region of DPPC monolayers. At a critical pressure pi(s) approximately 42 mN/m both Poxo- and PazePC induced a deflection in the pi-A isotherms, which could be rationalized in terms of reorientation of the oxidatively modified acyl chains into aqueous phase (adaptation of the so-called extended conformation), followed upon further film compression by solubilization of the oxidized phospholipids into the aqueous phase. Surface potential displayed a discontinuity at the same value of area/molecule, corresponding to the loss of the oxidized phospholipids from the monolayers. Our data support the view that lipid oxidation modifies both the small-scale structural dynamics of biological membranes as well as their more macroscopic lateral organization. Accordingly, oxidatively modified lipids can be expected to influence the organization and functions of membrane associated proteins.

MeSH Terms
1,2-Dipalmitoylphosphatidylcholine/chemistry Complex Mixtures/chemistry Lipid Bilayers/chemistry Lipid Peroxidation Liposomes/chemistry Membrane Fluidity Molecular Conformation Oxidation-Reduction Oxygen/chemistry Phospholipids/chemistry Solubility Structure-Activity Relationship
Chemicals
Complex Mixtures Lipid Bilayers Liposomes Phospholipids 1,2-Dipalmitoylphosphatidylcholine Oxygen
Authors & Affiliations
4 authors, click to expand affiliations / ORCID
Sabatini Karen
Dipartimento di Biochimica e Biologia Molecolare, Università di Bari, Centro di Studio sui Mitocondri e Metabolismo Energetico--CNR, Bari, Italy.
Mattila Juha-Pekka
Megli Francesco M
Kinnunen Paavo K J
References (60)
60 references, click to expand
  1. How proteins adapt to a membrane-water interface.
    Trends Biochem Sci. 2000 Sep;25(9):429-34 PMID: 10973056
  2. Domains in cell plasma membranes investigated by near-field scanning optical microscopy.
    Biophys J. 1998 May;74(5):2184-90 PMID: 9591645
  3. Fluorescence microscopy of phospholipid monolayer phase transitions.
    Chem Phys Lipids. 1991 Mar;57(2-3):227-39 PMID: 2054906
  4. Phospholipase A2 as a mechanosensor.
    Biophys J. 1995 May;68(5):1888-94 PMID: 7612831
  5. Dipole potential of lipid membranes.
    Chem Phys Lipids. 1994 Sep 6;73(1-2):57-79 PMID: 8001185
  6. Oxidative stress in malignant melanoma and non-melanoma skin cancer.
    Br J Dermatol. 2003 May;148(5):913-22 PMID: 12786821
  7. Repair of oxidative damage to DNA: enzymology and biology.
    Annu Rev Biochem. 1994;63:915-48 PMID: 7979257
  8. Interaction of reactive oxygen species with ion transport mechanisms.
    Am J Physiol. 1998 Jul;275(1 Pt 1):C1-24 PMID: 9688830
  9. Oxidants, antioxidants, and the degenerative diseases of aging.
    Proc Natl Acad Sci U S A. 1993 Sep 1;90(17):7915-22 PMID: 8367443
  10. Lipid-protein interactions in biological membranes: a structural perspective.
    Biochim Biophys Acta. 2003 May 2;1612(1):1-40 PMID: 12729927
  11. Implications of oxidative stress and cell membrane lipid peroxidation in human cancer (Spain).
    Cancer Causes Control. 2004 Sep;15(7):707-19 PMID: 15280629
  12. Evidence of oxidative damage in Alzheimer's disease brain: central role for amyloid beta-peptide.
    Trends Mol Med. 2001 Dec;7(12):548-54 PMID: 11733217
  13. Gel to liquid crystalline phase transition promotes a conformational reorganization of Ca2+, Mg2+-ATPase from sarcoplasmic reticulum in dimyristoylphosphatidylcholine reconstituted systems.
    Arch Biochem Biophys. 1987 Jan;252(1):303-14 PMID: 2949696
  14. Oxidized phospholipids induce phase separation in lipid vesicles.
    FEBS Lett. 2005 Aug 29;579(21):4577-84 PMID: 16098528
  15. The fluid mosaic model of the structure of cell membranes.
    Science. 1972 Feb 18;175(4023):720-31 PMID: 4333397
  16. Lipid domains in model and biological membranes.
    Chem Phys Lipids. 1994 Sep 6;73(1-2):121-37 PMID: 8001178
  17. Phospholipid-cytochrome c interaction: evidence for the extended lipid anchorage.
    J Biol Chem. 2002 Mar 15;277(11):8822-6 PMID: 11781329
  18. The interfacial elastic packing interactions of galactosylceramides, sphingomyelins, and phosphatidylcholines.
    Biophys J. 1996 Feb;70(2):868-77 PMID: 8789104
  19. Fusion of lipid bilayers: a model involving mechanistic connection to HII phase forming lipids.
    Chem Phys Lipids. 1992 Dec;63(3):251-8 PMID: 1493616
  20. Control of a redox reaction on lipid bilayer surfaces by membrane dipole potential.
    Biophys J. 2001 Jan;80(1):294-304 PMID: 11159402
  21. Effects of mitochondrial respiratory stimulation on membrane lipids and proteins: an electron paramagnetic resonance investigation.
    Biochim Biophys Acta. 1998 Jul 17;1372(2):163-73 PMID: 9675268
  22. Oxidized alkyl phospholipids are specific, high affinity peroxisome proliferator-activated receptor gamma ligands and agonists.
    J Biol Chem. 2001 May 11;276(19):16015-23 PMID: 11279149
  23. Lipid spin labels in lecithin multilayers. A study of motion along fatty acid chains.
    J Mol Biol. 1971 Jul 14;59(1):77-98 PMID: 4326898
  24. The major lipid peroxidation product, trans-4-hydroxy-2-nonenal, preferentially forms DNA adducts at codon 249 of human p53 gene, a unique mutational hotspot in hepatocellular carcinoma.
    Carcinogenesis. 2002 Nov;23(11):1781-9 PMID: 12419825
  25. Lipids do influence protein function-the hydrophobic matching hypothesis revisited.
    Biochim Biophys Acta. 2004 Nov 3;1666(1-2):205-26 PMID: 15519316
  26. Lateral organization in Acholeplasma laidlawii lipid bilayer models containing endogenous pyrene probes.
    Eur J Biochem. 2003 Apr;270(8):1699-709 PMID: 12694183
  27. Properties of lipid microdomains in a muscle cell membrane visualized by single molecule microscopy.
    EMBO J. 2000 Mar 1;19(5):892-901 PMID: 10698931
  28. Role of lipid peroxidation in the epidemiology and prevention of breast cancer.
    Cancer Epidemiol Biomarkers Prev. 2005 Dec;14(12):2829-39 PMID: 16364997
  29. Redox imbalance.
    Cell Tissue Res. 2004 Oct;318(1):201-13 PMID: 15365815
  30. How lipids affect the activities of integral membrane proteins.
    Biochim Biophys Acta. 2004 Nov 3;1666(1-2):62-87 PMID: 15519309
  31. Monolayer characteristics of saturated 1,2,-diacyl phosphatidylcholines (lecithins) and phosphatidylethanolamines at the air-water interface.
    Biochim Biophys Acta. 1968 Nov 5;163(3):301-13 PMID: 5721894
  32. Aging and caloric restriction affect mitochondrial respiration and lipid membrane status: an electron paramagnetic resonance investigation.
    Free Radic Biol Med. 1997;23(2):191-201 PMID: 9199881
  33. Structural and dynamic effects of oxidatively modified phospholipids in unsaturated lipid membranes.
    Biochemistry. 1992 Nov 10;31(44):10901-7 PMID: 1329957
  34. Lipid bilayers as osmotic response elements.
    Cell Physiol Biochem. 2000;10(5-6):243-50 PMID: 11125202
  35. Revisiting the fluid mosaic model of membranes.
    Science. 1995 Jun 9;268(5216):1441-2 PMID: 7770769
  36. Periodic structures in lipid monolayer phase transitions.
    Proc Natl Acad Sci U S A. 1984 May;81(10):3249-53 PMID: 16593467
  37. The role of oxidized lipoproteins in atherogenesis.
    Free Radic Biol Med. 1996;20(5):707-27 PMID: 8721615
  38. Lipid monolayers: why use half a membrane to characterize protein-membrane interactions?
    Curr Opin Struct Biol. 1999 Aug;9(4):438-43 PMID: 10449364
  39. Lipid peroxidation: a novel and unifying concept of the etiology of renal cell carcinoma (United States).
    Cancer Causes Control. 2002 Apr;13(3):287-93 PMID: 12020111
  40. Role of oxidative damage in the pathogenesis of viral infections of the nervous system.
    Histol Histopathol. 2005 Jul;20(3):957-67 PMID: 15944946
  41. EPR studies of phospholipid bilayers after lipoperoxidation. 1. Inner molecular order and fluidity gradient.
    Chem Phys Lipids. 2003 Oct;125(2):161-72 PMID: 14499474
  42. On the principles of functional ordering in biological membranes.
    Chem Phys Lipids. 1991 Mar;57(2-3):375-99 PMID: 2054913
  43. Antioxidant enzymes and lipid peroxidation in different forms of schizophrenia treated with typical and atypical antipsychotics.
    Schizophr Res. 2006 Jan 31;81(2-3):291-300 PMID: 16309894
  44. Synthetic peptides as models for intrinsic membrane proteins.
    FEBS Lett. 2003 Nov 27;555(1):134-8 PMID: 14630333
  45. Role of peroxidases in Parkinson disease: a hypothesis.
    Free Radic Biol Med. 2005 May 15;38(10):1296-310 PMID: 15855048
  46. Inhibitory effect of dipyridamole and its derivatives on lipid peroxidation in mitochondria.
    Free Radic Biol Med. 1997;23(7):1046-54 PMID: 9358248
  47. Accelerated accumulation of amyloid beta proteins on oxidatively damaged lipid membranes.
    Biochemistry. 2000 Aug 15;39(32):10011-6 PMID: 10933822
  48. Biomarkers of lipid peroxidation, airway inflammation and asthma.
    Eur Respir J. 2003 Jan;21(1):177-86 PMID: 12570126
  49. Mitochondrial phospholipid bilayer structure is ruined after liver oxidative injury in vivo.
    FEBS Lett. 2004 Aug 27;573(1-3):68-72 PMID: 15327977
  50. Lateral microheterogeneity of diphenylhexatriene-labeled choline phospholipids in the erythrocyte ghost membrane as determined by time-resolved fluorescence spectroscopy.
    J Membr Biol. 2000 Apr 1;174(3):237-43 PMID: 10758177
  51. Lipid dynamics and peripheral interactions of proteins with membrane surfaces.
    Chem Phys Lipids. 1994 Sep 6;73(1-2):181-207 PMID: 8001181
  52. Oxidants and the central nervous system: some fundamental questions. Is oxidant damage relevant to Parkinson's disease, Alzheimer's disease, traumatic injury or stroke?
    Acta Neurol Scand Suppl. 1989;126:23-33 PMID: 2694733
  53. Binding of cytochrome c to liposomes as revealed by the quenching of fluorescence from pyrene-labeled phospholipids.
    Biochemistry. 1987 Jun 2;26(11):2991-7 PMID: 3038173
  54. Correlation between bilayer lipid dynamics and activity of the diglucosyldiacylglycerol synthase from Acholeplasma laidlawii membranes.
    Biochemistry. 1996 Aug 6;35(31):10094-102 PMID: 8756472
  55. GPI-anchored proteins are organized in submicron domains at the cell surface.
    Nature. 1998 Aug 20;394(6695):798-801 PMID: 9723621
  56. Respiration state IV-generated ROS destroy the mitochondrial bilayer packing order in vitro. An EPR study.
    FEBS Lett. 2003 Aug 28;550(1-3):185-9 PMID: 12935908
  57. Oxidized phospholipids derived from ozone-treated lung surfactant extract reduce macrophage and epithelial cell viability.
    Chem Res Toxicol. 2002 Jul;15(7):896-906 PMID: 12118999
  58. Nitric oxide, superoxide, and peroxynitrite: the good, the bad, and ugly.
    Am J Physiol. 1996 Nov;271(5 Pt 1):C1424-37 PMID: 8944624
  59. Relation between various phospholipase actions on human red cell membranes and the interfacial phospholipid pressure in monolayers.
    Biochim Biophys Acta. 1975 Sep 16;406(1):97-107 PMID: 1174576
  60. Role of free radicals and catalytic metal ions in human disease: an overview.
    Methods Enzymol. 1990;186:1-85 PMID: 2172697
Article Info
Journal
Biophysical journal
Abbr.
Biophys J
ISSN
0006-3495
Published
2006-06-15
Epub
2006-00-31
Pages
4488-99
Language
English
Region
United States
NLM ID
0370626
PMCID
PMC1471873
Subset
IM
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: [email protected]