Magnetically aligned bicelles to study the orientation of lipophilic ligands in membrane bilayers

Journal of Medicinal Chemistry

Volumn 51, Issue 21, 2008, Pages 6793-6799

  Guo, Jianxin ^a   Yang, De Ping ^b   Chari, Ravi ^a   Tian, Xiaoyu ^a   Pavlopoulos, Spiro ^c   Lu, Dai ^a   Makriyannis, Alexandros ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

^b Department of Biology   (United States)

^c UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CANNABINOID; DELTA8 TETRAHYDROCANNABINOL; O METHYL DELTA8 TETRAHYDROCANNABINOL; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; BILAYER MEMBRANE; DEUTERON NUCLEAR MAGNETIC RESONANCE; DRUG CONFORMATION; DRUG STRUCTURE; LIPID BILAYER; LIPOPHILICITY; MAGNETISM; MOLECULAR DYNAMICS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; SIMULATION; SPECTROMETER;

COMPUTER SIMULATION; HYDROPHOBICITY; LIGANDS; LIPID BILAYERS; MAGNETIC RESONANCE SPECTROSCOPY; MAGNETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 56249123302     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800766x     Document Type: Article

References (38)

1. Gawrisch, K.; Eldho, N. V.; Polozov, I. V. Novel NMR tools to study structure and dynamics of biomembranes. Chem. Phys. Lipids 2002, 116, 135-151.
2. Seelig, J. Deuterium magnetic resonance: theory and applications in lipid membranes. Q. Rev. Biophys. 1977, 10, 353-418.
3. Smith, R. L.; Oldfield, E. Dynamic structure of membranes by deuterium NMR. Science 1984, 225, 280-287.
4. Ketchum, R. R.; Hu, W.; Cross, T. A. High-resolution conformation of gramicidin A in a lipid bilayer by solid-state NMR. Science 1993, 261, 1457-1460.
5. Moll, F., III.; Cross, T. A. Optimizing and characterizing alignment of oriented lipid bilayers containing gramicidin D. Biophys. J. 1990, 57, 351-362.
6. Sanders, C. R.; Hare, B. J.; Howard, K. P.; Prestegard, J. H. Magnetically-oriented phospholipid micelles as a tool for the study of membrane-associated molecules. Prog. Nucl. Magn. Reson. Spectrosc. 1994, 26, 421-444.
7. Howard, K. P.; Prestegard, J. H. Conformation and dynamics of membrane-bound digalactosyldiacylglycerol. J. Am. Chem. Soc. 1996, 118, 3345-3353.
8. Chou, J. J.; Kaufman, J. D.; Stahl, S. J.; Wingfield, P. T.; Bax, A. Micelle-induced curvature in a water-insoluble HIV-1 Env peptide revealed by NMR dipolar coupling measurement in stretched polyacrylamide gel. J. Am. Chem. Soc. 2002, 124, 2450-2451.
9. Matsumori, N.; Morooka, A.; Murata, M. Detailed description of the conformation and location of membrane-bound erythromycin a using isotropic bicelles. J. Med. Chem. 2006, 49, 3501-3508.
10. Whiles, J. A.; Brasseur, R.; Glover, K. J.; Melacini, G.; Komives, E. A.; Void, R. R. Orientation and effects of mastoparan X on phospholipid bicelles. Biophys. J. 2001, 80, 280-293.
11. De Angelis, A. A.; Jones, D. H.; Grant, C. V.; Park, S. H.; Mesleh, M. F.; Opella, S. J. NMR experiments on aligned samples of membrane proteins. Methods Enzymol. 2005, 394, 350-382.
12. Park, S. H.; De Angelis, A. A.; Nevzorov, A. A.; Wu, C. H.; Opella, S. Three-dimensional structure of the transmembrane domain of Vpu from HIV-1 in aligned phospholipid bicelles. Biophys. J. 2006, 91, 3032-3042.
13. Prosser, R S.; Evanics, F.; Kitevski, J. L.; Al-Abdul-Wahid, M. S. Current applications of bicelles in NMR studies of membrane-associated amphiphiles and proteins. Biochemistry 2006, 45, 8453-8465.
14. Marcotte, I.; Auger, M. Bicelles as model membranes for solid- and solution-state NMR studies of membrane peptides and proteins. Concepts Magn. Reson. 2005, 24A, 17-37.
15. Guo, J.; Pavlopoulos, S.; Tian, X.; Lu, D.; Nikas, S. P.; Yang, D.-P.; Makriyannis, A. Conformational study of lipophilic ligands in phospholipid model membrane systems by solution NMR. J. Med. Chem. 2003, 46, 4838-1846.
16. Guo, J.; Tian, X.; Pavlopoulos, S.; Makriyannis, A. Phospholipid Bicelle Membrane Systems for Studying Drug Molecules. In Modern Magnetic Resonance Part II, Applications in Medical and Pharmaceutical Sciences; Webb, G. A., Ed.; Springer: Dordrecht, The Netherlands, 2006; pp 1253-1259.
17. Yang, D. P.; Banijamali, A.; Charalambous, A.; Marciniak, G.; Makriyannis, A. Solid state deuterium-NMR as a method for determining the orientation of cannabinoid analogs in membranes. Pharmacol., Biochem. Behav. 1991, 40, 553-557.
18. Losonczi, J. A.; Prestegard, J. H. Improved dilute bicelle solutions for high-resolution NMR of biological macromolecules. J. Biomol. NMR 1998, 12, 447-151.
19. Sanders, C. R.; Prosser, R. S. Bicelles: a model membrane system for all seasons. Structure 1998, 6, 1227-1234.
20. Sternin, E.; Nizza, D.; Gawrisch, K. Temperature dependence of DMPC/DHPC mixing in a bicellar solution and its structural implications. Langmuir 2001, 17, 2610-2616.
21. Banijamali, A. R.; Charalambous, A.; van der Schyf, C. J.; Makriyannis, A. Specific deuteration of phenols and aromatic ethers using boron trifluoride and deuterium oxide. J. Labelled Compd. Radiopharm. 1987, 24, 1479-1482.
22. 8-THC and its O-methyl analog using differential scanning calorimetry, X-ray diffraction and solid state deuterium NMR experiments. Biochim. Biophys. Acta 1992, 1103, 25-36.
23. Falck, E.; Patra, M.; Karttunen, M.; Hyvönen, M. T.; Vattulainen, I. Lessons of slicing membranes: interplay of packing, free area, and lateral diffusion in phospholipid/cholesterol bilayers. Biophys. J. 2004, 87, 1076-1091.
24. Patra, M.; Karttunen, M.; Hyvönen, M. T.; Falck, E.; Lindqvist, P.; Vattulainen, I. Molecular dynamics simulations of lipid bilayers: major artifacts due to truncating electrostatic interactions. Biophys. J. 2003, 84, 3636-3645.
25. Tieleman, D. P. http://moose.bio.ucalgary.ca/index.php?page= Structures_and_Topologies.
26. Darden, T.; York, D.; Pederson, L. Particle mesh Ewald: an N·log(N) method for Ewald sums in large systems. J. Chem. Phys. 1993, 98, 10089-10092.
27. Berendsen, H. J. C.; van der Spoel, D.; van Drunen, R. GROMACS: a message-passing parallel molecular dynamics implementation. Comput. Phys. Commun. 1995, 91, 43-56.
28. Arnold, A.; Labrot, T.; Oda, R.; Dufourc, E. J. Cation modulation of bicelle size and magnetic alignment as revealed by solid-state NMR and electron microscopy. Biophys. J. 2002, 83, 2667-2680.
29. 13C-NMR. Biochim. Biophys. Acta 1990, 1028, 31-12.
30. 2H-NMR. Biochim. Biophys. Acta 1983, 737, 117-171.
31. 2H NMR studies of the effects of cholesterol on the acyl chain dynamics of magnetically aligned phospholipid bilayers. Magn. Reson. Chem. 2004, 42, 132-138.
32. 9-tetrahydrocannabinolic acid B. Acta Chem. Scand., Ser. B 1975, 29, 379-384.
33. 9,11-tetrahydrocannabinols in solution using high resolution nuclear magnetic resonance spectroscopy. Mol. Pharmacol. 1989, 35, 495-503.
34. Tieleman, D. P.; Berendsen, H. J. C. Molecular dynamics simulations of a fully hydrated dipalmitoylphosphatidylcholine bilayer with different macroscopic boundary conditions and parameters. J. Chem. Phys. 1996, 105, 4871-1880.
35. Schuettelkopf, A. W.; van Aalten, D. M. F. PRODRG, a tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallogr. 2004, D60, 1355-1363.
36. Makriyannis, A. The Role of Cell Membranes in Cannabinoid Activity. In Cannabinoid Receptors; Pertwee, R. G., Ed.; Academic Press: London, U.K., 1995; pp 87-115.
37. Makriyannis, A.; Tian, X.; Guo, J. How lipophilic cannabinergic ligands reach their receptor sites. Prostaglandins Other Lipid Mediators 2005, 77, 210-218.
38. Tian, X.; Guo, J.; Yao, F.; Yang, D.-P.; Makriyannis, A. The conformation, location, and dynamic properties of the endocannabinoid ligand anandamide in a membrane bilayer. J. Biol. Chem. 2005, 280, 29788-29795.