Binding of serotonin to lipid membranes

Journal of the American Chemical Society

Volumn 135, Issue 6, 2013, Pages 2164-2171

  Peters, Günther H ^a   Wang, Chunhua ^b   Cruys Bagger, Nicolaj ^b   Velardez, Gustavo F ^a   Madsen, Jesper J ^a   Westh, Peter ^b  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b ROSKILDE UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ANIMAL KINGDOM; AROMATIC RING SYSTEM; CARBONYL GROUPS; IN-MOLE-FRACTION; LIPID CHAINS; LIPID MATRIX; LIPID MEMBRANES; MD SIMULATION; MEMBRANE AFFINITY; MEMBRANE INTERFACE; MODEL MEMBRANES; MOLECULAR DYNAMICS SIMULATIONS; NEURAL TRANSMISSION; NON-SPECIFIC INTERACTIONS; OIL-WATER; PARTITIONING COEFFICIENTS; PHOSPHATE GROUP; PRIMARY AMINES; RECENT RESEARCHES; SEROTONIN RECEPTORS; SPECIFIC BINDING; SPECIFIC INTERACTION; SYNAPTIC MEMBRANES; THERMODYNAMIC MEASUREMENTS;

LIPID BILAYERS; MOLECULAR DYNAMICS; NEUROPHYSIOLOGY; ORGANIC COMPOUNDS;

MEMBRANES;

AMINE; CARBONYL DERIVATIVE; LIPID; NEUROTRANSMITTER; PHOSPHATE; PHOSPHORYLCHOLINE; SEROTONIN; SODIUM CHLORIDE; WATER;

ARTICLE; BILAYER MEMBRANE; BINDING AFFINITY; CHEMICAL INTERACTION; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; ENTROPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHILICITY; LIPID BILAYER; LIPID MEMBRANE; MEMBRANE BINDING; MOLECULAR DYNAMICS; NEUROTRANSMISSION; PROTEIN BINDING; PROTON TRANSPORT; THERMODYNAMICS;

BINDING SITES; LIPID BILAYERS; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; SEROTONIN;

EID: 84873630396     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja306681d     Document Type: Article

References (77)

1. Schreier, S.; Malheiros, S. V. P.; de Paula, E. Biochim. Biophys. Acta 2000, 1508, 210-234
2. Scheidt, H. A.; Huster, D. Acta Pharmacol. Sin. 2008, 29, 35-49
3. Nury, H.; Van Renterghem, C.; Weng, Y.; Tran, A.; Baaden, M.; Dufresne, V.; Changeux, J.-P.; Sonner, J. M.; Delarue, M.; Corringer, P. J. Nature 2011, 469, 428-431
4. Hemmings, H. C., Jr.; Akabas, M. H.; Goldstein, P. A.; Trudell, J. R.; Orser, B. A.; Harrison, N. L. Trends Pharmacol. Sci. 2005, 26, 503-510
5. Cantor, R. S. Biochemistry 1997, 36, 2339-2344
6. Turkyilmaz, S.; Mitomo, H.; Chen, W.-H.; Regen, S. L. Langmuir 2010, 26, 5309-5311
7. Bezrukov, S. M. Curr. Opin. Colloid Interface Sci. 2000, 5, 237-243
8. Weinrich, M.; Rostovtseva, T. K.; Bezrukov, S. M. Biochemistry 2009, 48, 5501-5503
9. Cantor, R. S. Chem. Phys. Lipids 1999, 101, 45-56
10. Mouritsen, O. G.; Bloom, M. Annu. Rev. Biophys. Biomol. Struct. 1993, 22, 145-171
11. Harroun, T. A.; Heller, W. T.; Weiss, T. M.; Yang, L.; Huang, H. W. Biophys. J. 1999, 76, 937-945
12. Søgaard, R.; Ebert, B.; Klaerke, D.; Werge, T. Biochim. Biophys. Acta 2009, 1788, 1073-1080
13. Søgaard, R.; Werge, T. M.; Bertelsen, C.; Lundbye, C.; Madsen, K. L.; Nielsen, C. H.; Lundbæk, J. A. Biochemistry 2006, 45, 13118-13129
14. Yang, L.; Sonner, J. M. Anesthesia Analgesia 2008, 107, 868-874
15. Milutinovic, P. S.; Yang, L.; Cantor, R. S.; Eger, E. I.; Sonner, J. M. Anesthesia Analgesia 2007, 105, 386-392
16. Mohr, J. T.; Gribble, G. W.; Lin, S. S.; Eckenhoff, R. G.; Cantor, R. S. J. Med. Chem. 2005, 48, 4172-4176
17. Cantor, R. S. Biochemistry 2003, 42, 11891-11897
18. Wang, C.; Ye, F.; Velardez, G. F.; Peters, G. H.; Westh, P. J. Phys. Chem. B 2011, 115, 196-203
19. Peters, G. H. Computer Simulations: A tool for investigating the function of complex biological macromolecules. In Enzyme functionality: Design, engineering, and screening; Svendsen, A., Ed.; Marcel Dekker, Inc.: New York, 2004; pp 97-147.
20. Peters, G. H. Recent Res. Devel. Biophys. 2004, 3, 501-526
21. Ash, W. L.; Zlomislic, M. R.; Oloo, E. O.; Tieleman, D. P. Biochim. Biophys. Acta 2004, 1666, 158-189
22. Stouch, T. R. Prog. Colloid Polym. Sci. 1997, 103, 116-120
23. Pandit, S. A.; Chiu, S. W.; Jakobsson, E.; Grama, A.; Scott, H. L. Biophys. J. 2008, 24, 6858-6865
24. Bennett, W. F.; MacCallum, J. L.; Tieleman, D. P. J. Am. Chem. Soc. 2009, 131, 1972-1978
25. Li, C.; Yi, M.; Hu, J.; Zhou, H. X.; Cross, T. A. Biophys. J. 2008, 94, 1295-1302
26. Johansson, A. C.; Lindahl, E. Proteins 2008, 70, 1332-1344
27. MacCallum, J. L.; Bennett, W. F.; Tieleman, D. P. Biophys. J. 2008, 94, 3393-3404
28. Tu, K.; Tarek, M.; Klein, M. L.; Scharf, D. Biophys. J. 1998, 75, 2123-2134
29. Orsi, M.; Sanderson, W. E.; Essex, J. W. J. Phys. Chem. B 2009, 113, 12019-12029
30. Available from http://chem2.sis.nlm.nih.gov/chemidplus/.
31. Pratuangdejkul, J.; Nosoongnoen, W.; Guérin, G.-A.; Loric, S.; Conti, M.; Launay, J.-M.; Manivet, P. Chem. Phys. Lett. 2006, 420, 538-544
32. Sonne, J.; Jensen, M.Ø.; Hansen, F. Y.; Hemmingsen, L.; Peters, G. H. Biophys. J. 2007, 92, 4157-4167
33. Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graph. 1996, 14, 33-38
34. Jørgensen, A. M.; Tagmose, L.; Jørgensen, A. M.; Bøgesø, K. P.; Peters, G. H. ChemMedChem 2007, 2, 827-840
35. Jørgensen, A. M.; Tagmose, L.; Jørgensen, A. M.; Topiol, S.; Sabio, M.; Gundertofte, K.; Bøgesø, K. P.; Peters, G. H. ChemMedChem 2007, 2, 815-826
36. MacKerell, A. D., Jr.; Bashford, D.; Bellott, M.; Dunbrack, R., Jr.; Evanseck, J.; Field, M.; Fischer, S.; Gao, J.; Guo, H.; Ha, S.; Joseph-McCarthy, D.; Kuchnir, L.; Kuczera, K.; Lau, F.; Mattos, C.; Michnick, S.; Smith, S.; Stote, R.; Straub, J.; Watanabe, M.; Wiorkiewicz-Kuczedra, J.; Yin, D.; Karplus, M. J. Phys. Chem. B 1998, 102, 3586-3616
37. Phillips, J. C.; Braun, R.; Wang, W.; Gumbart, J.; Tajkhorshid, E.; Villa, E.; Chipot, C.; Skeel, R. D.; Kale, L.; Schulten, K. J. Comput. Chem. 2005, 26, 1781-1802
38. Jorgensen, W. L.; Chandrasekhar, J.; Medura, J. D.; Impey, R. W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926-935
39. Nagle, J. F.; Zhang, S.; Tristram-Nagle, S.; Sun, W.; Petrache, H. I.; Suter, R. M. Biophys. J. 1996, 70, 1419-1431
40. Essmann, U.; Perera, L.; Berkowitz, M. L.; Darden, T.; Lee, H.; Pedersen, L. G. J. Chem. Phys. 1995, 103, 8577-8593
41. Peters, G. H.; Hansen, F. Y.; Moeller, M. S.; Westh, P. J. Phys. Chem. B 2009, 113, 92-102
42. Grossfield, A. WHAM: the weighted histogram analysis method, Version 2.0.6; 2012, (http://membrane.urmc.rochester.edu/content/wham).
43. Neale, C.; Bennett, W. F. D.; Tieleman, D. P.; Pomes, R. J. Chem. Theory Comput. 2011, 7, 4175-4188
44. MacCallum, J. L.; Tieleman, D. P. J. Am. Chem. Soc. 2006, 128, 125-130
45. Hub, J. S.; De Groot, B. L. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 1198-1203
46. Wang, C.; Ge, Y.; Mortensen, J.; Westh, P. J. Phys. Chem. B 2011, 115, 9955-9961
47. Westh, P. Biophys. J. 2003, 84, 341-349
48. Kupiainen, M.; Falck, E.; Ollila, S.; Niemela, P.; Gurtovenko, A. A.; Hyvonen, M. T.; Patra, M.; Karttunen, M.; Vattulainen, I. J. Comput. Theor. Nanosci. 2005, 2, 401-413
49. Bauer, M.; Megret, C.; Lamure, A.; Lacabanne, C.; Fauranclavel, M. J. J. Pharm. Sci. 1990, 79, 897-901
50. Andersen, H. D.; Wang, C.; Arleth, L.; Peters, G. H.; Westh, P. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 1874-1878
51. Chattopadhyay, A.; Rukmini, R.; Mukherjee, S. Biophys. J. 1996, 71, 1952-1960
52. Seeger, H. M.; Gudmundsson, M. L.; Heimburg, T. J. Phys. Chem. B 2007, 111, 13858-13866
53. Mastrangelo, S. V. R.; Dornte, R. W. J. Am. Chem. Soc. 1955, 77, 6200-6201
54. Katz, Y.; Diamond, J. M. J. Membr. Biol. 1974, 17, 101-120
55. Rowe, E. S.; Zhang, F. L.; Leung, T. W.; Parr, J. S.; Guy, P. T. Biochemistry 1998, 37, 2430-2440
56. Kamaya, H.; Kaneshina, S.; Ueda, I. Biochim. Biophys. Acta 1981, 646, 142
57. Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525-616
58. Amidon, G. L.; Yalkowsky, S. H.; Leung, S. J. Pharm. Sci. 1974, 63, 1858-1866
59. Westh, P.; Trandum, C.; Koga, Y. Biophys. Chem. 2001, 89, 53-63
60. Westh, P.; Trandum, C. Biochim. Biophys. Acta 1999, 1421, 261-272
61. Kang, S.; Green, J. P. Nature 1969, 222, 794-795
62. Hansch, C.; Leo, A.; Hoekman, D. Exploring QSAR, Hydrophobic, electronic and steric constants; American Chemical Society: Washington, DC, 1995; Vol. 2.
63. Tatsumi, H.; Ueda, T. J. Electroanal. Chem. 2011, 655, 180-183
64. Sonne, J.; Hansen, F. Y.; Peters, G. H. J. Chem. Phys. 2005, 122, 1-9
65. Pedersen, U. R.; Peters, G. H.; Westh, P. Biophys. Chem. 2007, 125, 104-111
66. Pedersen, U. R.; Leidy, C.; Westh, P.; Peters, G. H. Biochim. Biophys. Acta 2006, 1758, 573-582
67. Chiu, S. W.; Jakobsson, E.; Subramanian, S.; Scott, H. L. Biophys. J. 1999, 77, 2462-2469
68. De Vries, A. H.; Mark, A. E.; Marrink, S. J. J. Phys. Chem. B 2004, 108, 2454-2463
69. Douliez, J.-P.; Leonard, A.; Dufourc, E. J. Biophys. J. 1995, 68, 1727-1739
70. Seelig, A.; Seelig, J. Biochemistry 1974, 13, 4839-4845
71. Mehler, E. L.; Fuxreiter, M.; Simon, I.; Garcia-Moreno, E, B. Proteins: Struct., Funct. Genet. 2002, 48, 283-292
72. Peters, G. H.; Dahmen-Levison, U.; de Meijere, K.; Brezesinski, G.; Toxvaerd, S.; Svendsen, A.; Kinnunen, P. K. J. Langmuir 2000, 16, 2779-2788
73. Macartney, D. H. Isr. J. Chem. 2011, 51, 600-615
74. Hamilton, J. A.; Cistola, D. P. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 82-86
75. Tieleman, D. P. Clin. Exp. Pharmacol. Physiol. 2006, 33, 893-903
76. Nagle, J. F.; Tristram-Nagle, S. Biochim. Biochim. Acta 2000, 1469, 159
77. Heimburg, T.; Jackson, D. Biophys. J. 2007, 92, 3159-3165