Binding of nonsteroidal anti-inflammatory drugs to DPPC: structure and thermodynamic aspects.

The effect of nonsteroidal anti-inflammatory drugs (NSAIDs) on the phase transition and phase properties of 1,2-dipalmitoylphosphatidylcholine (DPPC) has been investigated in both 2D (monolayers at the air/water interface) and 3D (multilayers in lipid/water dispersions) model systems. The 2D membrane models have been characterized by means of pressure-area isotherms and grazing incidence X-ray diffraction (GIXD) measurements. Differential scanning calorimetry (DSC) and simultaneous small- and wide-angle X-ray diffraction have been applied to lipid aqueous dispersions. All NSAIDs studied altered the main transition temperature of the gel to liquid-crystalline phase transition, with the arylacetic acid derivatives (acemetacin and indomethacin) showing the largest effects. A comparison of the results reveals distinct structural features of the membrane models after interaction with the NSAID. All drugs induced perturbations in the lipid liquid-crystalline phase, suggesting a major change in the hydration behavior of DPPC. Again, the largest effects on the structural parameters are found for the arylacetic acid derivatives. The results obtained in the different model systems give indications of the role of the membrane/NSAID interactions that might also be important for NSAID gastric injury.

[1]  H. Davenport.  GASTRIC MUCOSAL INJURY BY FATTY AND ACETYLSALICYLIC ACIDS. , 1964, Gastroenterology.

[2]  J. Smith,et al.  Aspirin selectively inhibits prostaglandin production in human platelets. , 1971, Nature: New biology.

[3]  T. E. Thompson,et al.  Studies on the anomalous thermotropic behavior of aqueous dispersions of dipalmitoylphosphatidylcholine-cholesterol mixtures. , 1978, Biochemistry.

[4]  S. Hwang,et al.  Membrane effects of antiinflammatory agents. 2. Interaction of nonsteroidal antiinflammatory drugs with liposome and purple membranes. , 1981, Journal of medicinal chemistry.

[5]  T. L. Lemke,et al.  beta-Adrenergic blocking agents. alpha- and gamma-methyl(aryloxy)propanolamines. , 1981, Journal of medicinal chemistry.

[6]  M. Sporn,et al.  Polypeptide transforming growth factors isolated from bovine sources and used for wound healing in vivo. , 1983, Science.

[7]  B. Butler,et al.  Role of surface-active phospholipids in gastric cytoprotection. , 1983, Science.

[8]  R. Suter,et al.  Structure of the fully hydrated gel phase of dipalmitoylphosphatidylcholine. , 1989, Biophysical journal.

[9]  O. G. Mouritsen,et al.  A general model for the interaction of foreign molecules with lipid membranes: drugs and anaesthetics. , 1991, Biochimica et biophysica acta.

[10]  TIME-RESOLVED X-RAY DIFFRACTION STUDIES ON BIOLOGICAL SYSTEMS , 1992 .

[11]  G. Giammona,et al.  Effect of the complexation of some nonsteroidal anti-inflammatory drugs with β-cyclodextrin on the interaction with phosphatidylcholine liposomes , 1992 .

[12]  D. Lasič,et al.  Liposomes: From Physics to Applications , 1993 .

[13]  G. Mundy.  Boning up on genes , 1994, Nature.

[14]  K. Kjaer.  Some simple ideas on X-ray reflection and grazing-incidence diffraction from thin surfactant films , 1994 .

[15]  K. Jørgensen,et al.  Dynamical order and disorder in lipid bilayers. , 1994, Chemistry and physics of lipids.

[16]  K. Kjaer,et al.  Principles and applications of grazing incidence X-ray and neutron scattering from ordered molecular monolayers at the air-water interface , 1994 .

[17]  M. Giraud,et al.  Non-steroidal anti-inflammatory drugs (NSAIDs) associate with zwitterionic phospholipids: Insight into the mechanism and reversal of NSAID-induced gastrointestinal injury , 1995, Nature Medicine.

[18]  G. Rapp,et al.  A dual detector single readout system for simultaneous small (SAXS) and wide-angle X-ray (WAXS) scattering , 1995 .

[19]  J. Botting,et al.  Improved Non-Steroid Anti-Inflammatory Drugs: COX-2 Enzyme Inhibitors , 1996, Springer Netherlands.

[20]  J. Wallace.  Nonsteroidal anti-inflammatory drugs and gastroenteropathy: the second hundred years. , 1997, Gastroenterology.

[21]  J. Vane,et al.  Mechanism of action of nonsteroidal anti-inflammatory drugs. , 1998, The American journal of medicine.

[22]  P. Dutta,et al.  Structure and phase transitions in Langmuir monolayers , 1999 .

[23]  M. Giraud,et al.  Interaction of indomethacin and naproxen with gastric surface-active phospholipids: a possible mechanism for the gastric toxicity of nonsteroidal anti-inflammatory drugs (NSAIDs). , 1999, Biochemical pharmacology.

[24]  C. Krenn,et al.  New evidence for gel-liquid crystalline phase coexistence in the ripple phase of phosphatidylcholines , 2000, European Biophysics Journal.

[25]  V. Cardile,et al.  Calorimetric study on the interaction of thienopyrimidine derivatives with phosphatidylcholine membranes , 2003 .

[26]  K. Viras,et al.  Effects of non-steroid anti-inflammatory drugs in membrane bilayers. , 2004, Chemistry and physics of lipids.

[27]  Peter York,et al.  A Central Composite Design to Investigate the Thermal Stabilization of Lysozyme , 1999, Pharmaceutical Research.

[28]  S. Reis,et al.  Influence of some anti-inflammatory drugs in membrane fluidity studied by fluorescence anisotropy measurementsPresented at the 17th Conference of the European Colloid & Interface Science Society, Firenze, Italy, September 21?26, 2003 , 2004 .

[29]  E. Assem,et al.  Effect of cyclosporin analogues on histamine release from rat peritoneal mast cells and rat basophilic leukaemia cells , 1995, Inflammation Research.

[30]  J. Wallace,et al.  Correlations between changes in indicators of gastric mucosal barrier integrity at time of exposure to “barrier breakers” and extent of hemorrhagic erosions one hour later , 2005, Digestive Diseases and Sciences.

[31]  H. Waldmann,et al.  Membrane binding of a lipidated N-Ras protein studied in lipid monolayers , 2007, European Biophysics Journal.