Comparative biophysical studies of sartan class drug molecules losartan and candesartan (CV-11974) with membrane bilayers

Journal of Physical Chemistry B

Volumn 115, Issue 19, 2011, Pages 6180-6192

  Fotakis, Charalambos ^a,b   Christodouleas, Dionysios ^a,b   Zoumpoulakis, Panagiotis ^a   Kritsi, Eftichia ^a,b   Benetis, Nikolas Ploutarch ^a   Mavromoustakos, Thomas ^a,b   Reis, Heribert ^a   Gili, Argiro ^a,c   Papadopoulos, Manthos G ^a   Zervou, Maria ^a  

^a INSTITUTE OF BIOLOGY   (Greece)

^b UNIVERSITY OF ATHENS   (Greece)

^c NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON FIBER REINFORCED PLASTICS; DRUG INTERACTIONS; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHOLIPIDS;

2D-NMR SPECTROSCOPY; AB INITIO COMPUTATIONS; ACTIVE SITE; ALKYL CHAIN; BILAYER SURFACE; BIOPHYSICAL STUDIES; CANDESARTAN; DRUG MOLECULES; DYNAMIC PROPERTY; HYDROPHOBIC REGIONS; LATERAL DIFFUSION; LIPID CORES; LOSARTAN; MEMBRANE BILAYERS; MEMBRANE MODELS; MESOPHASES; MICRO-DOMAINS; NMR SPECTROSCOPY; PHARMACOLOGICAL PROPERTIES; POLAR HEADGROUPS; POLAR INTERACTIONS; TETRAZOLES; WATER INTERFACE;

LIPID BILAYERS;

EID: 79956091106     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp110371k     Document Type: Article

References (64)

1. Gasparo, M. D.; Catt, K. J.; Inagami, T.; Wright, J. W.; Ugner, T. Pharmacol. Rev. 2000, 52, 415-472
2. Wagenaar, L. J.; Voors, A. A.; Buikema, H.; van Buiten, A.; Lübeck, R. H.; Boonstra, P. W.; van Veldhuisen, D. J.; van Gilst, W. H. Cardiovasc. Drugs Ther. 2002, 16, 311-316
3. Unger, T. Eur. Heart J. Suppl. 2004, 6, H11-H16
4. Morsing, P.; Vauquelin, G. Cell. Biochem. Biophys. 2001, 35, 89-102
5. Zou, Y.; Akazawa, H.; Qin, Y.; Sano, M.; Takano, H.; Minamino, T.; Makita, N.; Iwanaga, K.; Zhu, W.; Kudoh, S.; Toko, H.; Tamura, K.; Kihara, M.; Nagai, T.; Fukamizu, A.; Umemura, S.; Iiri, T.; Fujita, T.; Komuro, I. Nat. Cell Biol. 2004, 6, 499-506
6. Yasuda, N.; Miura, S.; Akazawa, H.; Tanaka, T.; Qin, Y.; Kiya, Y.; Imaizumi, S.; Fujino, M.; Ito, K.; Zou, Y.; Fukuhara, S.; Kunimoto, S.; Fukuzaki, K.; Sato, T.; Ge, J.; Mochizuki, N.; Nakaya, H.; Saku, K.; Komuro, I. EMBO Rep. 2008, 9, 179-186
7. Zoumpoulakis, P.; Daliani, I.; Zervou, M.; Kyrikou, I.; Lamprinidis, G.; Mikros, E.; Mavromoustakos, T. Chem. Phys. Lipids 2003, 125, 13-25
8. Vauquelin, G.; Packeu, A. Mol. Cell. Endocrinol. 2009, 311, 1-10
9. Rumiana, K.; Caffrey, M. Biochim. Biophys. Acta 1998, 1376, 91-145
10. Tristram-Nagle, S.; Wiener, M. C.; Yang, C. P.; Nagle, J. F. Biochemistry 1987, 26, 4288-4294
11. Houslay, M. D.; Stanley, K. K. Dynamics of Biological Membranes; John Wiley & Sons: New York, 1982.
12. Rand, R. P.; Chapman, D.; Larsson, K. J. Biophys. 1975, 15, 1117-1124
13. Stamatoff, J.; Feuer, B.; Guggenheim, H. J.; Tellez, G.; Yamane, T. J. Biophys. 1982, 38, 217-226
14. McIntosh, T. J. J. Biophys. 1980, 29, 237-246
15. Colthup, N. B.; Daly, L. H.; Wiberley, S. E. Introduction to Infrared and Raman Spectroscopy; Academic Press: New York, 1990.
16. Huang, C.; Lapides, J. R.; Levin, I. W. J. Am. Chem. Soc. 1982, 104, 5926-5930
17. Levin, I. W.; Lewis, E. N. Anal. Chem. 1990, 62, 1101A-1111A
18. Pabst, G.; Rappolt, M.; Amenitsch, H.; Laggner, P. Phys. Rev. E 2000, 62, 4000-4009
19. Silvius, J. R.; Lyons, M.; Yeagle, P. L.; OLeary, T. J. Biochemistry 1985, 24, 5388-5395
20. Netticadan, T. J.; Ashavaid, T. F.; Nair, K. G. Indian J. Clin. Biochem. 1997, 12, 49-54
21. Theodoropoulou, E.; Mavromoustakos, T.; Panagiotopoulos, D.; Matsoukas, J.; Smith, J. Lett. Pept. Sci. 1996, 3, 209-216
22. Matsoukas, J. M.; Agelis, G.; Wahhab, A.; Hondrelis, J.; Panagiotopoulos, D.; Yamdagni, R.; Wu, Q.; Mavromoustakos, T.; Maia, H. L. S.; Ganter, R.; Moore, G. J. J. Med. Chem. 1995, 38, 4660-4669
23. Zoumpoulakis, P.; Zoga, A.; Roumelioti, P.; Giatas, N.; Grdadolnik, S. G.; Iliodromitis, E.; Vlahakos, D.; Kremastinos, D.; Matsoukas, J.; Mavromoustakos, T. J. Pharm. Biomed. Anal. 2003, 31, 833-844
24. Moutevelis-Minakakis, P.; Gianni, M.; Stougiannou, H.; Zoumpoulakis, P.; Zoga, A.; Vlahakos, A. D.; Iliodromitis, E.; Mavromoustakos, T. Bioorg. Med. Chem. Lett. 2003, 13, 1737-1740
25. Mavromoustakos, T.; Moutevelis-Minakakis, P.; Kokotos, C. G.; Kontogianni, P.; Politi, A.; Zoumpoulakis, P.; Findlay, J.; Cox, A.; Balmforth, A.; Zoga, A.; Iliodromitis, E. Bioorg. Med. Chem. 2006, 14, 4353-4360
26. Zoumpoulakis, P.; Politi, A.; Grdadolnik, S. G.; Matsoukas, J.; Mavromoustakos, T. J. Pharm. Biomed. Anal. 2006, 40, 1097-1104
27. Mavromoustakos, T.; Apostolopoulos, V.; Matsoukas, J. Med. Chem. 2001, 1, 207-217
28. Mavromoustakos, T.; Zervou, M.; Zoumpoulakis, P.; Kyrikou, I.; Benetis, N. P.; Polevaya, L.; Roumelioti, P.; Giatas, N.; Zoga, A.; Moutevelis Minakakis, P.; Kolocouris, A.; Vlahakos, D.; Grdadolnik, S. G.; Matsoukas, J. Curr. Top. Med. Chem. 2004, 4, 385-401
29. Fotakis, C.; Christodouleas, D.; Chatzigeorgiou, P.; Zervou, M.; Benetis, N. P.; Viras, K.; M. Mavromoustakos, T. Biophys. J. 2009, 96, 2227-2236
30. Potamitis, C.; Chatzigeorgiou, P.; Siapi, E.; Viras, K.; Mavromoustakos, T.; Hodzic, A.; Pabst, G.; Cacho-Nerin, F.; Laggner, P.; Rappolt, M. Biochim. Biophys. Acta 2011, DOI: 10.1016/j.bbamem. 2011.02.002
31. Dasgupta, C.; Zhang, L. Drug Discovery Today 2011, 16, 22-34
32. Naik, P.; Murumkar, P.; Giridha, R.; Yadav, M. R. Bioorg. Med. Chem. 2010, 18, 8418-8456
33. Kyrikou, I.; Poulos, C.; Benetis, N.; Viras, K.; Zervou, M.; Mavromoustakos, T. Biochim. Biophys. Acta 2008, 1778, 113-124
34. MacroModel, version 9.8; Schrödinger, LLC: New York, NY, 2010.
35. Jorgensen, W. L.; Tirado-Rives, J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 6665-6670
36. QikProp, version 3.3; Schrödinger, LLC: New York, NY, 2010.
37. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
38. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
39. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654
40. Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618-622
41. Kutzelnigg, W. Isr. J. Chem. 1980, 19, 193-199
42. Schindler, M.; Kutzelnigg, W. J. Chem. Phys. 1982, 76, 1919-1933
43. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, J. R. E.; Burant, C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.9; Gaussian, Inc.: Pittsburgh PA, 1998.
44. Anet, F. A. L.; OLeary, D. J. Concepts Magn. Reson. 1991, 3, 193-214
45. Soteriadou, K. P.; Tzinia, K. P.; Panou-Pomonis, A. K.; Tsikaris, V.; Sakarellos-Daitsiotis, M.; Sakarellos, C.; Papapoulou, Y.; Matsas, R. Biochem. J. 1996, 313, 455-466
46. Zoumpoulakis, P.; Grdadolnik, S. G.; Matsoukas, J.; Mavromoustakos, T. J. Pharm. Biomed. Anal. 2002, 28, 125-135
47. Kyonova, R.; Caffrey, M. Biochim. Biophys. Acta 1998, 1376, 91-145
48. Theodoropoulou, E.; Marsh, D. Biochim. Biophys. Acta 1999, 1461, 135-146
49. Theodoropoulou, E.; Marsh, D. Biochim. Biophys. Acta 2000, 1509, 346-360
50. Mavromoustakos, T.; Yang, D. P.; Makriyannis, A. Biochim. Biophys. Acta 1995, 1239, 257-264
51. Mavromoustakos, T.; Chatzigeorgiou, P.; Koukoulitsa, C.; Durdagi, S. Int. J. Quantum Chem. 2011, 111, 1172-1183
52. McMullen, T. P.; McElhaney, R. N. Biochim. Biophys. Acta 1995, 1234, 90-98
53. Vist, M. R.; Davis, J. H. Biochemistry 1990, 29, 451-464
54. OLeary, T. J.; Ross, P. D.; Levin, I. W. Biochemistry 1984, 23, 4636-4641
55. OLeary, T. J.; Levin, I. W. Biochim. Biophys. Acta 776 1984, 776, 185-189
56. Yeagle, P. L. Biol. Magn. Reson. 1990, 9, 153-155
57. Harrold, M. Foyes Principles of Medicinal Chemistry, 5 th ed.; Williams, D. A.; Lemke, T. L., Eds.; Lippincott Williams & Wilkins: Philadelphia, 2002.
58. Lombardi, D.; Cuenoud, B.; Kramer, S. D. Eur. J. Pharm. Sci. 2009, 38, 533-547
59. Tian, X.; Pavlopoulos, S.; De-Ping, Y.; Makriyannis, A. Biochim. Biophys. Acta 2010, doi: 10.1016/j.bbamem.2010.11.026
60. Mavromoustakos, T.; Kolocouris, A.; Zervou, M.; Roumelioti, P; Matsoukas, J.; Weisemann, R. J. Med. Chem. 1999, 42, 1714-1722
61. Potamitis, C.; Zervou, M.; Katsiaras, V.; Zoumpoulakis, P.; Durdagi, S.; Papadopoulos, M. G.; Hayes, J. M.; Grdadolnik-Golic, S.; Kyrikou, I.; Argyropoulos, D.; Vatougia, G.; Mavromoustakos, T. J. Chem. Inf. Model. 2009, 49, 726-739
62. Tomohiro, K.; Kejun, C.; Kenner, R. C.; Gawrisch, K. Biophys. J. 2009, 96, 4916-4924
63. Lucio, M; Lima, J. L. F. C.; Reis, S. Curr. Med. Chem. 2010, 17, 1795-1809
64. Ojima, M.; Inada, Y.; Shibouta, Y.; Wada, T.; Sanada, T.; Kubo, K.; Nishikawa, K. Eur. J. Pharmacol. 1997, 319, 137-146