Interactions of the AT1 antagonist valsartan with dipalmitoyl-phosphatidylcholine bilayers

Biochimica et Biophysica Acta - Biomembranes

Volumn 1808, Issue 6, 2011, Pages 1753-1763

  Potamitis, C ^a,b   Chatzigeorgiou, P ^b   Siapi, E ^a   Viras, K ^b   Mavromoustakos, T ^a,b   Hodzic, A ^c,d   Pabst, G ^c   Cacho Nerin, F ^c   Laggner, P ^c   Rappolt, M ^c  

^a INSTITUTE OF BIOLOGY   (Greece)

^b UNIVERSITY OF ATHENS   (Greece)

^c ERICH SCHMID INSTITUTE OF MATERIALS SCIENCE   (Austria)

^d RESEARCH CENTER PHARMACEUTICAL ENGINEERING GMBH   (Austria)

Author keywords

Bilayer; Differential scanning calorimetry; Dipalmitoyl phosphatidylcholine; Raman spectroscopy; Small angle and wide angle X ray scattering; Valsartan

Indexed keywords

ANGIOTENSIN 1 RECEPTOR; DIPALMITOYLPHOSPHATIDYLCHOLINE; VALSARTAN; ANGIOTENSIN 1 RECEPTOR ANTAGONIST; DRUG DERIVATIVE; TETRAZOLE DERIVATIVE; VALINE;

ARTICLE; CONCENTRATION RESPONSE; DRUG MECHANISM; ENTHALPY; HYDROPHOBICITY; LIPID BILAYER; LIQUID; MEMBRANE STRUCTURE; MOLECULAR INTERACTION; PHASE TRANSITION; PRIORITY JOURNAL; ALGORITHM; BINDING COMPETITION; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; DIFFERENTIAL SCANNING CALORIMETRY; KINETICS; METABOLISM; RAMAN SPECTROMETRY; SMALL ANGLE SCATTERING; TEMPERATURE; THERMODYNAMICS; X RAY DIFFRACTION;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; ALGORITHMS; ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKERS; BINDING, COMPETITIVE; CALORIMETRY, DIFFERENTIAL SCANNING; KINETICS; LIPID BILAYERS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SCATTERING, SMALL ANGLE; SPECTRUM ANALYSIS, RAMAN; TEMPERATURE; TETRAZOLES; THERMODYNAMICS; VALINE; X-RAY DIFFRACTION;

EID: 79954794881     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2011.02.002     Document Type: Article

References (88)

1. M. Paul, A.P. Mehr, and R. Kreutz Physiology of local renin-angiotensin systems Physiol. Rev. 86 2006 747 803 (Pubitemid 44033382)
2. M. De Gasparo, K.J. Catt, T. Inagami, J.W. Wright, and Th. Unger International Union of Pharmacology. XXIII. The angiotensin II receptors Pharmacol. Rev. 52 2000 415 472
3. B. Rubin, M.J. Antonaccio, and Z.P. Horovitz Captopril (SQ 14, 225) (D-3-mercapto-2-methylpropanoyl-L-proline): a novel orally active inhibitor of angiotensin-converting enzyme and antihypertensive agent Progr. Cardiovascular Diseases 21 1978 183 194 (Pubitemid 9068239)
4. C.I. Johnston Angiotensin receptor antogonists: focus on losartan Lancet 346 1995 1403 1407
5. J.L. Pool, M. Azizi, M. Azizi, J.-C. Aldigier, A. Januszewicz, W. Zidek, and Y. Chiang Aliskiren, an orally effective renin inhibitor, provides sntihypertensive efficacy alone and in combination with valsartan J. Am. Hypert. 20 2007 11 20 (Pubitemid 46014059)
6. C. Sakarellos, K. Lintner, F. Piriou, and S. Fermandjian Conformation of the central sequence of angiotensin II and analogs Biopolymers 22 1983 663 687 (Pubitemid 13101812)
7. P.C. Wong, T.B. Barnes, A.T. Chiu, D.D. Christ, J.V. Duncia, W.F. Herblin, and P.B.M.W.M. Timmermans Losartan (DuP 753), an orally active nonpeptide angiotensin II receptor antagonist Cardiovasc. Drug Rev. 9 1991 317 339
8. I. Martin, and J.M. Ruysschaert Common properties of fusion peptides from diverse systems Biosci. Rep. 20 2000 483 500 (Pubitemid 32523207)
9. E.L. Schiffrin Vascular and cardiac benefits of angiotensin receptor blockers Am. J. Med. 113 2002 409 418 (Pubitemid 35230007)
10. L.M. Ruilope, E.A. Rosei, G.L. Bakris, G. Mancia, N.R. Poulter, S. Taddei, T. Unger, M. Volpe, B. Waeber, and F. Zannad Angiotensin receptor blockers: therapeutic targets and cardiovascular protection Blood Press. 14 2005 196 209 (Pubitemid 41387809)
11. G. Reboldi, F. Angeli, C. Cavallini, G. Gentile, G. Mancia, and P. Verdecchia Comparison between angiotensin-converting enzyme inhibitors and angiotensin receptor blockers on the risk of myocardial infarction, stroke and death: a meta-analysis J. Hypertens. 26 2008 1282 1289
12. T. Mavromoustakos, A. Kolocouris, M. Zervou, P. Roumelioti, J.M. Matsoukas, and R. Weisemann An effort to understand the molecular basis of hypertension through the study of conformational analysis of losartan and sarmesin using a combination of Nuclear Magnetic Resonance spectroscopy and theoretical calculations J. Med. Chem. 42 1999 1714 1722 (Pubitemid 29244965)
13. P. Zoumpoulakis, A. Zoga, P. Roumelioti, N. Giatas, S.G. Grdadolnik, E. Iliodromitis, D. Vlahakos, D. Kremastinos, J.M. Matsoukas, and T. Mavromoustakos Conformational and biological studies for a pair of novel synthetic AT1 antagonists. Stereoelectronic requirements for antihypertensive efficacy J. Pharm. Biomed. Anal. 31 2003 833 844 (Pubitemid 36397942)
14. P. Zoumpoulakis, A. Politi, S.G. Grdadolnik, J.M. Matsoukas, and T. Mavromoustakos Structure elucidation and conformational study of V8. A novel synthetic non peptide AT1 antagonist J. Pharm. Biomed. Anal. 40 2006 1097 1104 (Pubitemid 43247446)
15. T. Mavromoustakos, M. Zervou, P. Zoumpoulakis, I. Kyrikou, N.P. Benetis, L. Polevaya, P. Roumelioti, N. Giatas, A. Zoga, P.M. Minakakis, A. Kolocouris, D. Vlahakos, S.G. Grdadolnik, and J.M. Matsoukas Conformation and bioactivity. Design and discovery of novel antihypertensive drugs Curr. Top. Med. Chem. 4 2004 385 401 (Pubitemid 38854830)
16. T. Mavromoustakos, P. Zoumpoulakis, I. Kyrikou, A. Zoga, E. Siapi, M. Zervou, I. Daliani, D. Dimitriou, A. Pitsasa, C. Kamoutsis, and P. Laggner Efforts to understand the molecular basis of hypertension trough drug:membrane interactions Curr. Top. Med. Chem. 4 2004 445 459 (Pubitemid 38864690)
17. J.N. Cohn, and G. Tognoni A randomized trial of the angiotensin-receptor blocker valsartan in chronic heart failure N. Engl. J. Med. 345 2001 1667 1675 (Pubitemid 33126822)
18. A. Chiolero, and M. Burnier Pharmocology of valsartan, an angiotensin II receptor antagonist Expert Opin. Invest. Drugs 7 1998 1915 1925 (Pubitemid 28505096)
19. M. De Gasparo, and S. Whitebread Binding of valsartan to mammalian angiotensin AT1 receptors Regul. Pept. 59 1995 503 511
20. P. Buhlmayer, P. Furret, L. Criscione, M. De Gasparo, S. Whitebread, T. Schildin, R. Lattmann, and J. Wood Valsartan, a potent orally active angiotensin II antagonist developed from structurally new aminoacid series Bioorg. Med. Chem. Lett. 4 1994 29 34 (Pubitemid 24128681)
21. Y. Furukawa, S. Kishimoto, K. Nishikawa, Hypotensive Imidazole-5-Acetic Acid Derivatives. U.S. Patent 4355040, (1982).
22. P. Zoumpoulakis, I. Daliani, M. Zervou, I. Kyrikou, E. Siapi, G. Lamprinidis, E. Mikros, and T. Mavromoustakos Losartan's molecular basis of interaction with membranes and AT1 receptor Chem. Phys. Lipids 125 2003 13 25 (Pubitemid 37414802)
23. C. Fotakis, S. Gega, E. Siapi, C. Potamitis, K. Viras, P. Moutevelis-Minakakis, C.G. Kokotos, S. Durdagi, S. Golic Grdadolnik, B. Sartori, M. Rappolt, and T. Mavromoustakos Interactions at the bilayer interface and receptor site induced by the novel synthetic pyrrolidinone analog MMK3 Biochim. Biophys. Acta 1768 2010 422 432
24. L.G. Herbette Pharmacokinetic and pharmacodynamic design of lipophilic drugs based on a structural model for drug-interactions with biological membranes Pesticide Sc. 35 1992 363 368
25. H.S. Young, V. Skita, R.P. Mason, and L.G. Herbette Molecular-basis for the inhibition of 1, 4-dihydropyridine calcium-channel drugs binding to their receptors by a non-specific site interaction mechanism Biophys. J. 61 1992 1244 1255
26. T. Mavromoustakos, D.P. Yang, and A. Makriyannis Small angle x-ray diffraction and differential scanning calorimetric studies on O-methyl-(-)-Δ8 tetrahydrocannabinol and its 5′ iodinated derivative in membrane bilayers Biochim. Biophys. Acta 1237 1995 183 188
27. M. McIntyre, S.E. Gaffe, R.A. Michaluck, and J.L. Reid Losartan, an orally active angiotensin (AT1) receptor antagonist: a review of its efficacy and safety in essential hypertension Pharmacol. Ther. 74 1997 181 194 (Pubitemid 27337347)
28. F.A. Oliveira, R. Morgado, M.V. Lima, B.A. Mello, A. Hansen, and G.G. Batrouni Comment on "dynamical foundations of nonextensive statistical mechanics" Phys. Rev. Lett. 90 2003 218901
29. T.J. Netticadan, T.F. Ashavaid, and K.G. Nair Characterisation of the canine cardiac sarcolemma in experimental mzocardial ischemia Indian J. Clin. Biochem. 12 1997 49 54
30. R. Koynova, and M. Caffrey Phases and phase transitions of the phosphatidylcholines Biochim. Biophys. Acta 1376 1998 91 145 (Pubitemid 28321526)
31. M.D. Housley, and K.K. Stanley Dynamics of Biological Membranes 1982 John Wiley and Sons New York
32. I.W. Levin, and R.N. Lewis Fourier transform Raman spectroscopy of biological materials Anal. Chem. 62 1990 1101A 1111A
33. J.C. Huang, J.R. Lapides, and I.W. Levin Phase-transition behaviour of saturated, symmetric chain phospholipid bilayers dispersions determined by Raman spectroscopy: correlation between spectral and thermodynamic parameters J. Am. Chem. Soc. 104 1982 5926 5930
34. M. Rappolt, and G. Pabst Flexibility and structure of fluid bilayer interfaces K. Nag, Structure and dynamics of membranous interfaces 2008 John Wiley & Sons Hoboken 45 81
35. G. Pabst, H. Amenitsch, D.P. Kharakoz, P. Laggner, and M. Rappolt Structure and fluctuations of phosphatidylcholines in the vicinity of the main phase transition Phys. Rev. E 70 2004 021908-1-021908-9
36. H. Amenitsch, M. Rappolt, M. Kriechbaum, H. Mio, P. Laggner, and S. Bernstorff First performance assessment of the small-angle X-ray scattering beamline at ELETTRA J. Synchrotron Rad. 5 1998 506 508
37. G. Pabst, M. Rappolt, H. Amenitsch, and P. Laggner Structural information from multilamellar liposomes at full hydration: full q-range fitting with high quality x-ray data Phys. Rev. E 62 2000 4000 4009
38. G. Pabst, J. Katsaras, V.A. Raghunathan, and M. Rappolt Structure and interactions in the anomalous swelling regime of phospholipid bilayers Langmuir 19 2003 1716 1722
39. G. Pabst Global properties of biomimetic membranes: perspectives on molecular features Biophys. Rev. Lett. 1 2006 57 84
40. M. Rappolt Bilayer thickness estimations with "poor" diffraction data J. Appl. Phys. 107 2010 art. no. 084701
41. J.F. Nagle, and S. Tristram-Nagle Structure and interactions of lipid bilayer: role of fluctuations J. Katsaras, T. Gutberlet, Lipid bilayers. Structure and interactions 2000 Springer Berlin 1 23
42. J.F. Nagle, and S. Tristram-Nagle Structure of lipid bilayers Biochim. Biophys. Acta 1469 2000 159 195
43. S.W. Chiu, E. Jakobsson, R.J. Mashl, and H.L. Scott Cholesterol-induced modifications in lipid bilayers: a simulation study Biophys. J. 83 2002 1842 1853
44. A. Hodzic, M. Rappolt, H. Amenitsch, and G. Pabst Differential modulation of membrane structure and fluctuations by plant sterols and cholesterol Biophys. J. 94 2008 3935 3944
45. A.I. Greenwood, S. Tristram-Nagle, and J.F. Nagle Partial molecular volumes of lipids and cholesterol Chem. Phys. Lipids 143 2006 1 10 (Pubitemid 44107906)
46. E. Marti, H.R. Oswald, P. Bühlmyer, W. Marterer, Valsartan salts, European Patent Bulletin EP1313714B1 (2008).
47. N. Albon, and J.M. Sturtevant Nature of the gel to liquid crystal transition of synthetic phosphatidylcholines Proc. Natl. Acad. Sci. USA 75 1978 2258 2260 (Pubitemid 8349418)
48. S. Tristram-Nagle, R. Zhang, R.M. Suter, C.R. Worthington, W.J. Sun, and J.F. Nagle Measurement of chain tilt angle in fully hydrated bilayers of gel phase lecithins Biophys. J. 64 1993 1097 1109 (Pubitemid 23143274)
49. J. Katsaras, S. Tristram-Nagle, Y. Liu, R.L. Headrick, E. Fontes, P.C. Mason, and J.F. Nagle Clarification of the ripple phase of lecithin bilayers using fully hydrated, aligned samples Phys. Rev. E 61 2000 5668 5677
50. R.C. Spiker, and I.W. Levin Raman spectra and vibrational assignments for dipalmitoyl phosphatidylcholine and structurally related molecules Biochim. Biophys. Acta 388 1975 361 373
51. N. Yellin, and I.W. Levin Hydrocarbon chain disorder in lipid bilayers: temperature dependent Raman spectra of 1, 2-diacyl phosphatidylcholine-water gels Biochim. Biophys. Acta 489 1977 177 190 (Pubitemid 8220198)
52. N. Yellin, and I.W. Levin Hydrocarbon chain trans-gauche isomerization in phospholipid bilayer gel assemblies Biochemistry 16 1977 642 647 (Pubitemid 8047802)
53. C.B. Fox, R.H. Uibel, and J.M. Harris Detecting phase transitions in phosphatidylcholine vesicles by Raman microscopy and self-modeling curve resolution J. Phys. Chem. B 111 2007 11428 11436 (Pubitemid 47598324)
54. T.J. O'Leary, P.D. Ross, and I.W. Levin Effects of anesthetic and nonanesthetic steroids on dipalmitoylphosphatidylcholine liposomes: a calorimetric and Raman spectroscopic investigation Biochemistry 23 1984 4636 4641 (Pubitemid 14012276)
55. N.B. Colthulp, L.H. Daly, and S.E. Wiberley Introduction to Infrared and Raman Spectroscopy 1990 Academic Press
56. R.K. Bista, R.F. Bruch, and A.M. Covington Variable-temperature Raman spectro-microscopy for a comprehensive analysis of the conformational order in PEGylated lipids J. RamanSpectrosc. 40 2008 463 471
57. T.J. O'Leary, and I.W. Levin Raman spectrosopic study of an interdigitated lipid bilayer diplamitoylphosphatidylcholine dispersed in glycerol Biochim. Biophys. Acta 776 1984 185 189
58. J.R. Silvius, M. Lyons, P.L. Yeagle, and T.J. O'Leary Thermotropic properties of bilyers containing blanched-chain phospholipids, calorimetric, Raman and 31P NMR studies Biochemistry 24 1985 5388 5395 (Pubitemid 16228815)
59. M. Rappolt, and G. Rapp Structure of the stable and metastable ripple phase of dipalmitoylphosphatidylcholine Eur. Biophys. J. 24 1996 381 386 (Pubitemid 26249047)
60. R. Hosemann, and S.N. Bagchi Direct Analysis of Diffraction by Matter 1962 North-Holland Publ. Co. Amsterdam
61. A. Caillé Remarques sur la diffusion des rayons X dans les smectiques A C. R. Acad. Sc. Paris B 274 1972 891 893
62. R. Zhang, S. Tristram-Nagle, W. Sun, R.L. Headrick, T.C. Irving, R.M. Suter, and J.F. Nagle Small-angle x-ray scattering from lipid bilayers is well described by modified Caillé theory but not by paracrystalline theory Biophys. J. 70 1996 349 357
63. A. Seelig, and J. Seelig The dynamic structure of fatty acyl chains in a phospholipid bilayer measured by deuterium magnetic resonance Biochemistry 13 1974 4839 4845
64. J.F. Nagle, and D.A. Wilkinson Lecithin bilayers. Density measurements and molecular interactions Biophys. J. 23 1978 159 175 (Pubitemid 8402557)
65. D.A. Wilkinson, and J.F. Nagle Dilatometry and calorimetry of saturated phosphatidylethanolamine dispersions Biochemistry 20 1981 187 192
66. W.J. Sun, S. Tristram-Nagle, R.M. Suter, and J.F. Nagle Structure of the ripple phase in lecithin bilayers Proc. Natl. Acad. Sci. USA 93 1996 7008 7012 (Pubitemid 26243491)
67. M. Rappolt, G. Pabst, G. Rapp, M. Kriechbaum, H. Amenitsch, C. Krenn, S. Bernstorff, and P. Laggner New evidence for gel-liquid crystalline phase coexistence in the ripple phase of phosphatidylcholines Eur. Biophys. J. 29 2000 125 133
68. R.J. Wittebort, C.F. Schmidt, and R.G. Griffin Solid-state carbon-13 nuclear magnetic resonance of the lecithin gel to liquid-crystalline phase transition Biochemistry 20 1981 4223 4228 (Pubitemid 11012534)
69. K. Pressl, K. Jørgensen, and P. Laggner Characterization of the sub-main-transition in distearoylphosphatidylcholine studied by simultaneous small- and wide-angle X-ray diffraction Biochim. Biophys. Acta 1325 1997 1 7 (Pubitemid 27138470)
70. K. Jørgensen Calorimetric detection of a sub-main transition in long-chain phosphatidylcholine lipid bilayers Biochim. Biophys. Acta 1240 1995 111 114 (Pubitemid 26004737)
71. K.A. Riske, R.P. Barroso, C.C. Vequi-Suplicy, R. Germano, V.B. Henriques, and M.T. Lamy Lipid bilayer pre-transition as the beginning of the melting process Biochim. Biophys. Acta 1788 2009 954 963
72. T. Heimburg A model for the lipid pretransition: coupling of ripple formation with the chain-melting transition Biophys. J. 78 2000 1154 1165 (Pubitemid 30141544)
73. K. Sengupta, V.A. Raghunathan, and J. Katsaras Novel structural features of the ripple phase of phospholipids Europhys. Lett. 49 2000 722 728
74. T.P. McMullen, and R.N. McElhaney New aspects of the interaction of cholesterol with dipalmitoylphosphatidylcholine bilayers as revealed by high-sensitivity differential scanning calorimetry Biochim. Biophys. Acta 1234 1995 90 98
75. M.R. Vist, and J.H. Davis Phase equilibria of cholesterol/ dipalmitoylphosphatidylcholine mixtures: 2 H nuclear magnetic resonance and differential scanning calorimetry Biochemistry 29 1990 451 464 (Pubitemid 20037653)
76. C. Fotakis, D. Christodouleas, P. Chatzigeorgiou, M. Zervou, N.-P. Benetis, K. Viras, and T. Mavromoustakos Development of a CP 31P NMR broadline simulation methodology for studying the interactions of antihypertensive AT1 antagonist losartan with phospholipid bilayers Biophys. J. 96 2009 2227 2236
77. E. Theodoropoulou, and D. Marsh Interactions of angiotensin II non-peptide AT1 antagonist losartan with phospholipid membranes studied by combined use of di¡erential scanning calorimetry and electron spin resonance spectroscopy Biochim. Biophys. Acta 1461 1999 135 146 (Pubitemid 30077469)
78. E.S. Rowe, and T.A. Cutrera Differential scanning calorimetric studies of ethanol interactions with distearoylphosphatidylcholine: transition to the interdigitated phase Biochemistry 29 1990 10398 10404 (Pubitemid 20384550)
79. I.W. Levin, T.E. Thompson, Y. Barenholz, and C. Huang Two types of hydrocarbon chain interdigitation in sphingomyelin bilayers Biochemistry 24 1985 6282 6286 (Pubitemid 16197385)
80. G.S. Smith, E.B. Sirota, C.R. Safinya, and N.A. Clark Structure of the L beta phases in a hydrated phosphatidylcholine multimembrane Phys. Rev. Lett. 60 1988 813 816
81. W.J. Sun, R.M. Suter, M.A. Knewtson, C.R. Worthington, S. Tristram-Nagle, R. Zhang, and J.F. Nagle Order and disorder in fully hydrated unoriented bilayers of gel phase dipalmitoylphosphatidylcholine Phys. Rev. E 49 1994 4665 4676
82. E. Sevcsik, G. Pabst, A. Jilek, and K. Lohner How lipids influence the mode of action of membrane-active peptides Biochim. Biophys. Acta 1768 2007 2586 2595 (Pubitemid 47532036)
83. S. Danner, G. Pabst, K. Lohner, and A. Hickel Structure and thermotropic behavior of the Staphylococcus aureus lipid lysyl- dipalmitoylphosphatidylglycerol Biophys. J. 94 2008 2150 2159
84. V.A. Parsegian, and R.P. Rand Interaction in membrane assemblies R. Lipowsky, E. Sackmann, Structure and Dynamics of Membranes 1995 North-Holland Amsterdam 643 690
85. G. Cevc Membrane electrostatics Biochim. Biophys. Acta 1031 1990 311 382
86. E. Cagigal, L. Gonzalez, R.M. Alonso, and R.M. Jimenez pKa determinination of angiotensin II receptor antagonists (ARA II) by spectrofluorimetry J. Pharm. Biomed. Anal. 26 2001 477 486 (Pubitemid 32727666)
87. M. Rappolt, M.F. Vidal, M. Kriechbaum, M. Steinhart, H. Amenitsch, S. Bernstorff, and P. Laggner Structural, dynamic and mechanical properties of POPC at low cholesterol concentration studied in pressure/temperature space Eur. Biophys. J. 31 2003 575 585 (Pubitemid 36286320)
88. H.I. Petrache, N. Gouliaev, S. Tristram-Nagle, R.T. Zhang, R.M. Suter, and J.F. Nagle Interbilayer interactions from high-resolution x-ray scattering Phys. Rev. E 57 1998 7014 7024 (Pubitemid 128625113)