Electrostatic contributions to indole-lipid interactions

Journal of Physical Chemistry B

Volumn 109, Issue 26, 2005, Pages 13014-13023

  Gaede, Holly C ^a   Yau, Wai Ming ^a   Gawrisch, Klaus ^a  

^a NATIONAL INSTITUTE ON ALCOHOL ABUSE AND ALCOHOLISM   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC MOLECULES; ESTER BONDS; INDOLE; STRUCTURAL TRANSITIONS;

CARBONYLATION; ETHERS; GLYCEROL; HYDROGEN BONDS; LIPIDS; NUCLEAR MAGNETIC RESONANCE; ORGANIC COMPOUNDS; PHASE TRANSITIONS; POLYMERIC MEMBRANES; PROTEINS; VAN DER WAALS FORCES;

ELECTROSTATICS;

CHOLINE; DEUTERIUM; INDOLE; INDOLE DERIVATIVE; PHOSPHOLIPID; PROTON; TRYPTOPHAN;

ARTICLE; CHEMISTRY; ELECTRICITY; LIPID BILAYER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STATIC ELECTRICITY;

CHOLINE; DEUTERIUM; ELECTROSTATICS; INDOLES; LIPID BILAYERS; MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHOLIPIDS; PROTONS; STATIC ELECTRICITY; TRYPTOPHAN;

EID: 22344440794     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0511000     Document Type: Article

References (35)

1. von Heijne, G. Membrane proteins: From sequence to structure. Annu. Rev. Biophys. Biomol. Struct. 1994, 23, 167-192.
2. Ketchem, R. R.; Hu, W.; Cross, T. A. High-resolution conformation of gramicidin-A in a lipid bilayer by solid-state NMR. Science 1993, 261 (5127), 1457-1460.
3. Hu, W.; Lee, K. C.; Cross, T. A. Tryptophans in membrane proteins: Indole ring orientations and functional implications in the gramicidin channel. Biochemistry 1993, 32 (27), 7035-7047.
4. Koeppe, R. E.; Killian, J. A.; Greathouse, D. V. Orientations of the tryptophan 9 and 11 side chains of the gramicidin channel based on deuterium nuclear magnetic resonance spectroscopy. Biophys. J. 1994, 66 (1), 14-24.
5. Durell, S. R.; Guy, H. R. Atomic scale structure and functional models of voltage-gated potassium channels. Biophys. J. 1992, 62 (1), 238-250.
6. Bogusz, S.; Boxer, A.; Busath, D. D. An SS1-SS2 β-barrel structure for the voltage-activated potassium channel. Protein Eng. 1992, 5 (4), 285-293.
7. Schiffer, M.; Chang, C. H.; Stevens, F. J. The functions of tryptophan residues in membrane proteins. Protein Eng. 1992, 5 (3), 213-214.
8. 2H NMR. Biophys. J. 1998, 75 (3), 1365-1371.
9. Morein, S.; Strandberg, E.; Killian, J. A.; Persson, S.; Arvidson, G.; Koeppe, R. E.; Lindblom, G. Influence of membrane-spanning α-helical peptides on the phase behavior of the dioleoylphosphatidylcholine/water system. Biophys. J. 1997, 73 (6), 3078-3088.
10. Killian, J. A.; Salemink, I.; de Planque, M. R. R.; Lindblom, G.; Koeppe, R. E.; Greathouse, D. V. Induction of nonbilayer structures in diacylphosphatidylcholine model membranes by transmembrane α-helical peptides: Importance of hydrophobic mismatch and proposed role of tryptophans. Biochemistry 1996, 35 (3), 1037-1045.
11. Jacobs, R. E.; White, S. H. The nature of the hydrophobic binding of small peptides at the bilayer interface: Implications for the insertion of transbilayer helices. Biochemistry 1989, 28 (8), 3421-3437.
12. Wimley, W. C.; White, S. H. Experimentally determined hydrophobicity scale for proteins at membrane interfaces. Nat. Struct. Biol. 1996, 3 (10), 842-848.
13. Wimley, W. C.; White, S. H. Partitioning of tryptophan side-chain analogs between water and cyclohexane (Erratum to 1992, 31, 12813-12818). Biochemistry 1993, 32 (35), 9262.
14. Yau, W. M.; Wimley, W. C.; Gawrisch, K.; White, S. H. The preference of tryptophan for membrane interfaces. Biochemistry 1998, 37 (42), 14713-14718.
15. Kachel, K.; Asuncion-Punzalan, E.; London, E. Anchoring of tryptophan and tyrosine analogs at the hydrocarbon polar boundary in model membrane vesicles: Parallax analysis of fluorescence quenching induced by nitroxide-labeled phospholipids. Biochemistry 1995, 34 (47), 15475-15479.
16. Dougherty, D. A. Cation-π interactions in chemistry and biology: A new view of benzene, Phe, Tyr, and Trp. Science 1996, 271 (5246), 163-168.
17. Woolf, T. B.; Grossfield, A.; Pearson, J. G. Indoles at interfaces: Calculations of electrostatic effects with density functional and molecular dynamics methods. Int. J. Quantum Chem. 1999, 75 (3), 197-206.
18. Suzuki, S.; Green, P. G.; Bumgarner, R. E.; Dasgupta, S.; Goddard, W. A.; Blake, G. A. Benzene forms hydrogen bonds with water. Science 1992, 257 (5072), 942-944.
19. Saiz, L.; Klein, M. L. Electrostatic interactions in a neutral model phospholipid bilayer by molecular dynamics simulations. J. Chem. Phys. 2002, 116 (7), 3052-3057.
20. 31P nuclear magnetic resonance and the head-group structure of phospholipids in membranes. Biochim. Biophys. Acta 1978, 515 (2), 105-140.
21. Pearson, R. H.; Pascher, I. The molecular structure of lecithin dihydrate. Nature 1979, 281 (5731), 499-501.
22. Gawrisch, K.; Ruston, D.; Zimmerberg, J.; Parsegian, V. A.; Rand, R. P.; Fuller, N. Membrane dipole potentials, hydration forces, and the ordering of water at membrane surfaces. Biophys. J. 1992, 61 (5), 1213-1223.
23. Yau, W. M.; Gawrisch, K. Deuteration of indole and N-methylindole by Raney nickel catalysis. J. Labelled Compd. Radiopharm. 1999, 42 (7), 709-713.
24. Davis, J. H.; Jeffrey, K. R.; Bloom, M.; Valic, M. I.; Higgs, T. P. Quadrupolar echo deuteron magnetic resonance spectroscopy in ordered hydrocarbon chains, Chem. Phys. Lett. 1976, 42, 390-394.
25. Sternin, E.; Bloom, M.; Mackay, A. L. De-Pak-ing of NMR spectra. J. Magn. Reson. 1983, 55 (2), 274-282.
26. Huster, D.; Arnold, K.; Gawrisch, K. Investigation of lipid organization in biological membranes by two-dimensional nuclear Overhauser enhancement spectroscopy. J. Phys. Chem. B 1999, 103 (1), 243-251.
27. Gaede, H. C.; Gawrisch, K. Lateral diffusion rates of lipid, water, and a hydrophobic drug in a multilamellar liposome. Biophys. J. 2003, 85(3), 1734-1740.
28. De Filippis, V.; De Boni, S.; De Dea, E.; Dalzoppo, D.; Grandi, C.; Fontana, A. Incorporation of the fluorescent amino acid 7-azatryptophan into the core domain 1-47 of hirudin as a probe of hirudin folding and thrombin recognition. Protein Sci. 2004, 13 (6), 1489-1502.
29. Feller, S. E.; Brown, C. A.; Nizza, D. T.; Gawrisch, K. Nuclear Overhauser enhancement spectroscopy cross-relaxation rates and ethanol distribution across membranes. Biophys. J. 2002, 82 (3), 1396-1404.
30. Feller, S. E.; Huster, D.; Gawrisch, K. Interpretation of NOESY cross-relaxation rates from molecular dynamics simulation of a lipid bilayer. J. Am. Chem. Soc. 1999, 121 (38), 8963-8964.
31. Yau, W. M.; Gawrisch, K. Lateral lipid diffusion dominates NOESY cross-relaxation in membranes. J. Am. Chem. Soc. 2000, 122 (16), 3971-3972.
32. Lewis, R. N. A. H.; Pohle, W.; McElhaney, R. N. The interfacial structure of phospholipid bilayers: Differential scanning calorimetry and Fourier transform infrared spectroscopic studies of 1,2-dipalmitoyl-sn-glycero-3- phosphorylcholine and its dialkyl and acyl-alkyl analogues. Biophys. J. 1996, 70 (6), 2736-2746.
33. Koenig, B. W.; Strey, H. H.; Gawrisch, K. Membrane lateral compressibility determined by NMR and X-ray diffraction: Effect of acyl chain polyunsaturation. Biophys. J. 1997, 73 (4), 1954-1966.
34. Nagle, J. F.; Tristram-Nagle, S. Structure of lipid bilayers. Biochim. Biophys. Acta 2000, 1469 (3), 159-195.
35. Verkleij, A. J.; Zwaal, R. F.; Roelofsen, B.; Comfurius, P.; Kastelijn, D.; van Deenen, L. L. The asymmetric distribution of phospholipids in the human red cell membrane. A combined study using phospholipases and freeze-etch electron microscopy. Biochim. Biophys. Acta 1973, 323 (2), 178-193.