Alignment of druglike compounds in lipid bilayers analyzed by solid-state 19F-NMR and molecular dynamics, based on dipolar couplings of adjacent CF3 groups

Journal of Physical Chemistry B

Volumn 116, Issue 16, 2012, Pages 4769-4782

  Dürr, Ulrich H N ^a,d   Afonin, Sergii ^a   Hoff, Barbara ^a,e   De Luca, Giuseppina ^b   Emsley, James W ^c   Ulrich, Anne S ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF CALABRIA   (Italy)

^c UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^d INFAI GmbH   (Germany)

^e BOS Obernburg   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALIGNMENT; COUPLINGS; DENSITY FUNCTIONAL THEORY; FLUORINE; LIQUID CRYSTALS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AMPHIPHILIC PROPERTY; BI-LAYER; BIOMEMBRANES; COMPLEX MOLECULES; DIPOLAR COUPLINGS; HOMONUCLEAR; LIPID MATRIX; LIPOPHILIC DRUGS; MODEL COMPOUND; MOLECULAR DYNAMICS SIMULATIONS; MOLECULAR SEGMENTS; MULTI-PULSE SEQUENCE; ORDER PARAMETER; PHENYL RINGS; PROBABILITY FUNCTIONS; RESIDUAL DIPOLAR COUPLINGS; SPIN INTERACTION; STRUCTURE AND DYNAMICS; TRIFLUOROMETHYL;

LIPID BILAYERS;

BENZOIC ACID DERIVATIVE; FLUORINE; FLUOROCARBON; PHENYLACETIC ACID; PHENYLACETIC ACID DERIVATIVE;

ALGORITHM; ARTICLE; CHEMISTRY; LIPID BILAYER; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALGORITHMS; BENZOATES; FLUORINE; FLUOROCARBONS; LIPID BILAYERS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR DYNAMICS SIMULATION; PHENYLACETATES;

EID: 84860304271     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp212339k     Document Type: Article

References (67)

1. Salgado, J.; Grage, S. L.; Kondejewski, L. H.; Hodges, R. S.; McElhaney, R. N.; Ulrich, A. S. J. Biomol. NMR 2001, 21, 191-208
2. Strandberg, E.; Ulrich, A. S. Concepts Magn. Reson. A 2004, 23, 89-120
3. Wi, S.; Sinha, N.; Hong, M. J. Am. Chem. Soc. 2004, 126, 12754-12755
4. Ulrich, A. S.; Wadhwani, P.; Dürr, U. H. N.; Afonin, S.; Glaser, R. W.; Strandberg, E.; Tremouilhac, P. P. Y.; Sachse, C.; Berditchevskaia, M.; Grage, S. L. Solid-state 19F-nuclear magnetic resonance analysis of membrane-active peptides. In NMR spectroscopy of biological solids; Ramamoorthy, A., Ed.; CRC Press: Boca Raton, FL, 2004; pp 215-36.
5. Ulrich, A. S. Prog. Nucl. Magn. Reson. Spectrosc. 2005, 46, 1-21
6. Kim, S. J.; Cegelski, L.; Preobrazhenskaya, M.; Schaefer, J. Biochemistry 2006, 45, 5235-5250
7. Patti, G. J.; Kim, S. J.; Yu, T.-Y.; Dietrich, E.; Tanaka, K. S. E.; Parr, T. R., Jr.; Far, A. R.; Schaefer, J. J. Mol. Biol. 2009, 392, 1178-1191
8. Marsh, E. N.; Buer, B. C.; Ramamoorthy, A. Mol. Biosyst. 2009, 5, 1143-1147
9. Ieronimo, M.; Afonin, S.; Koch, K.; Berditsch, M.; Wadhwani, P.; Ulrich, A. S. J. Am. Chem. Soc. 2010, 132, 8822-8824
10. Koch, K.; Afonin, S.; Ieronimo, M.; Berditsch, M.; Ulrich, A. S. Top. Curr. Chem. 2012, 306, 89-118
11. Glaser, R. W.; Ulrich, A. S. J. Magn. Reson. 2003, 164, 104-114
12. Ulrich, R.; Glaser, R. W.; Ulrich, A. S. J. Magn. Reson. 2003, 164, 115-127
13. Mikhailiuk, P. K.; Afonin, S.; Chernega, A. N.; Rusanov, E. B.; Platonov, M. O.; Dubinina, G. G.; Berditsch, M.; Ulrich, A. S.; Komarov, I. V. Angew. Chem., Int. Ed. 2006, 45, 5659-5661
14. Mykhailiuk, P. K.; Afonin, S.; Palamarchuk, G. V.; Shishkin, O. V.; Ulrich, A. S.; Komarov, I. V. Angewandte Chem. Int. Ed. 2008, 47, 5765-5767
15. Kubyshkin, V. S.; Komarov, I. V.; Afonin, S.; Mykhailiuk, P. K.; Grage, S. L.; Ulrich, A. S. In Fluorine in Pharmaceutical and Medicinal Chemistry: From Biophysical Aspects to Clinical Applications; Gouverneur, V.; Müllen, K., Eds.; Imperial College Press: London, 2012.
16. Strandberg, E.; Wadhwani, P.; Tremouilhac, P. P. Y.; Dürr, U. H. N.; Ulrich, A. S. Biophys. J. 2006, 90, 1676-1686
17. Afonin, S.; Mikhailiuk, P. K.; Komarov, I. V.; Ulrich, A. S. J. Pept. Sci. 2007, 13, 614-623
18. Glaser, R. W.; Sachse, C.; Dürr, U. H. N.; Wadhwani, P.; Ulrich, A. S. J. Magn. Reson. 2004, 168, 153-163
19. Glaser, R. W.; Sachse, C.; Dürr, U. H. N.; Wadhwani, P.; Afonin, S.; Strandberg, E.; Ulrich, A. S. Biophys. J. 2005, 88, 3392-3397
20. Afonin, S.; Dürr, U. H. N.; Wadhwani, P.; Glaser, R. W.; Ulrich, A. S. Top. Curr. Chem. 2008, 273, 139-154
21. Afonin, S.; Grage, S. L.; Ieronimo, M.; Wadhwani, P.; Ulrich, A. S. J. Am. Chem. Soc. 2008, 130, 16512-16514
22. Wadhwani, P.; Buerck, J.; Strandberg, E.; Mink, C.; Afonin, S.; Ulrich, A. S. J. Am. Chem. Soc. 2008, 130, 16515-16517
23. Maisch, D.; Wadhwani, P.; Afonin, S.; Böttcher, C.; Koksch, B.; Ulrich, A. S. J. Am. Chem. Soc. 2009, 131, 15596-15597
24. Grasnick, D.; Sternberg, U.; Strandberg, E.; Wadhwani, P.; Ulrich, A. S. Eur. Biophys. J. 2011, 40, 529-543
25. Grage, S. L.; Ulrich, A. S. J. Magn. Reson. 1999, 138, 98-106
26. Grage, S. L.; Ulrich, A. S. J. Magn. Reson. 2000, 146, 81-88
27. Grage, S. L.; Suleymanova, A. V.; Afonin, S.; Wadhwani, P.; Ulrich, A. S. J. Magn. Reson. 2006, 183, 77-86
28. Buffy, J. J; Waring, A. J.; Hong, M. J. Am. Chem. Soc. 2005, 127, 4477-4483
29. 19F. In Encyclopedia of spectroscopy and spectrometry; Lindon, J. C., Ed.; Academic Press: New York, 2000; pp 813-25.
30. Gilchrist, M. L., Jr.; Monde, K.; Tomita, Y.; Iwashita, T.; Nakanishi, K.; McDermott, A. E. J. Magn. Reson. 2001, 152, 1-6
31. Luo, W.; Mani, R.; Hong, M. J. Phys. Chem. B 2007, 111, 10825-10832
32. Witter, R.; Nozirov, F.; Sternberg, U.; Cross, T. A.; Ulrich, A. S.; Fu, R. J. Am. Chem. Soc. 2008, 130, 918-924
33. Grage, S. L.; Gauger, D. R.; Selle, C.; Pohle, W.; Richter, W.; Ulrich, A. S. Phys. Chem. Chem. Phys. 2000, 2, 4574-4579
34. Emsley, J. W. Liquid crystals: General considerations. In Encyclopedia of NMR; Grant, D. M.; Harris, R. K., Eds.; Wiley: New York, 1996; pp 2788-2799.
35. Emsley, J. W. Liquid crystalline samples: Structure of nonrigid molecules. In Encyclopedia of NMR; Grant, D. M.; Harris, R. K., Eds.; Wiley: New York, 1996; pp 2781-2787.
36. Diehl, P. Structure of rigid molecules dissolved in liquid crystalline solvents. In Encyclopedia of NMR; Grant, D. M.; Harris, R. K., Eds.; Wiley: New York, 1996; pp 4591-4602.
37. Algieri, C.; Castiglione, F.; Celebre, G.; De Luca, G.; Longeri, M.; Emsley, J. W. Phys. Chem. Chem. Phys. 2000, 2, 3405-3413
38. Levitt, M. H.; Freeman, R. J. Magn. Reson. 1979, 33, 473-476
39. Freeman, R.; Kempsell, S. P.; Levitt, M. H. J. Magn. Reson. 1980, 38, 453-479
40. Lindahl, E.; Hess, B.; van der Spoel, D. J. Mol. Model. 2001, 7, 306-317
41. Berger, O.; Edholm, O.; Jahnig, F. Biophys. J. 1997, 72, 2002-2013
42. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; DiNola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684-3690
43. Grage, S. L.; Dürr, U. H. N.; Afonin, S.; Mikhailiuk, P. K.; Komarov, I. V.; Ulrich, A. S. J. Magn. Reson. 2008, 191, 16-23
44. Engelsberg, M.; Yannoni, C. S. J. Magn. Reson. 1990, 88, 393-400
45. Celebre, G.; De Luca, G.; Longeri, M.; Sicilia, E. J. Chem. Inf. Comput. Sci. 1994, 34, 539-545
46. Longeri, M.; Celebre, G. Liquid crystalline samples: Spectral analysis. In Encyclopedia of NMR; Grant, D. M.,; Harris, R. K., Eds.; Wiley: New York, 1996; pp 2774-2781.
47. Castiglione, F.; Carravetta, M.; Celebre, G.; Longeri, M. J. Magn. Reson. 1998, 132, 1-12
48. Bak, M.; Rasmussen, T.; Nielsen, N. C. J. Magn. Reson. 2000, 147, 296-330
49. Englert, G.; Saupe, A. Z. Naturforsch. 1964, 19a, 172-177
50. Saupe, A. Z. Naturforsch. 1964, 19a, 161-171
51. Saupe, A. Angew. Chem., Int. Ed. 1968, 7, 97-112
52. Vaara, J.; Jokisaari, J.; Wasylishen, R. E.; Bryce, D. L. Prog. Nucl. Magn. Reson. Spectrosc. 2002, 41, 233-304
53. Emsley, J. W.; De Luca, G.; Lesage, A.; Longeri, M.; Mallory, F. B.; Mallory, C. W. Phys. Chem. Chem. Phys. 2008, 10, 6534-6543
54. Emsley, J. W. Liq. Cryst. 2010, 37, 913-921
55. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
56. Pileo, G. Ph.D. Thesis, Universita Della Calabria, 2004-2005.
57. Emsley, J. W.; Heeks, S. K.; Horne, T. J.; Howells, M. H.; Moon, A.; Palke, W. E.; Patel, S. U.; Shilstone, G. N.; Smith, A. Liq. Cryst. 1991, 9, 649-660
58. Hoff, B.; Strandberg, E.; Ulrich, A. S.; Tieleman, D. P.; Posten, C. Biophys. J. 2005, 88, 1818-1827
59. Petersen, N. O.; Chan, S. I. Biochemistry 1977, 16, 2657-2667
60. Tieleman, D. P.; Marrink, S.-J.; Berendsen, H. J. C. Biochim. Biophys. Acta 1997, 1331, 235-270
61. Schwarz, G.; Stankowski, S.; Rizzo, V. Biochim. Biophys. Acta 1986, 861, 141-151
62. Montich, G.; Scarlata, S.; McLaughlin, S.; Lehrmann, R.; Seelig, J. Biochim. Biophys. Acta 1993, 1146, 17-24
63. Ahumada, H.; Montecinos, R.; Tieleman, D. P.; Weiss-López, B. E. J. Phys. Chem. A 2005, 109, 6644-6651
64. Afonin, S.; Glaser, R. W.; Berditchevskaia, M.; Wadhwani, P.; Gührs, K.-H.; Möllmann, U.; Perner, A.; Ulrich, A. S. Chembiochem. 2003, 4, 1151-1163
65. Koubi, L.; Tarek, M.; Bandyopadhyay, S.; Klein, M. L.; Scharf, D. Biophys. J. 2001, 81, 3339-3345
66. Koubi, L.; Tarek, M.; Bandyopadhyay, S.; Klein, M. L.; Scharf, D. Anesthesiology 2002, 97, 848-855
67. Esteban-Martin, S.; Salgado, J. Biophys. J. 2007, 93, 4278-4288