Mutational mapping and modeling of the binding site for (S)-citalopram in the human serotonin transporter

Journal of Biological Chemistry

Volumn 285, Issue 3, 2010, Pages 2051-2063

  Andersen, Jacob ^a   Olsen, Lars ^a   Hansen, Kasper B ^a,c   Taboureau, Olivier ^b   Jørgensen, Flemming S ^a   Jørgensen, Anne Marie ^d   Bang Andersen, Benny ^d   Egebjerg, Jan ^d   Strømgaard, Kristian ^a   Kristensen, Anders S ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d H LUNDBECK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIDEPRESSANT DRUG; BINDING MODES; BINDING POCKETS; CITALOPRAM; COMPARATIVE MODELING; COMPUTATIONAL APPROACH; EXTRACELLULAR LEVELS; FLUOXETINE; LIGAND DOCKING; MOLECULAR DETERMINANTS; NEURONAL CELL; POINT MUTATIONS; SEROTONIN TRANSPORTERS; STRUCTURAL DATA; SUBSTRATE BINDING; SUBSTRATE-BINDING SITES; TRANSPORT FUNCTION;

BINDING ENERGY; BIOCHEMISTRY;

BINDING SITES;

CITALOPRAM; ESCITALOPRAM; SEROTONIN TRANSPORTER; DRUG DERIVATIVE; SEROTONIN; SEROTONIN UPTAKE INHIBITOR;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG BINDING SITE; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG TARGETING; MOLECULAR DOCKING; NONHUMAN; POINT MUTATION; PRIORITY JOURNAL; ANIMAL; BINDING SITE; CELL STRAIN COS1; CERCOPITHECUS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ENZYME SPECIFICITY; GENETICS; HUMAN; METABOLISM; MUTATION; NUCLEOTIDE SEQUENCE; PROTEIN CONFORMATION; REPRODUCIBILITY; SEQUENCE HOMOLOGY; STRUCTURE ACTIVITY RELATION; TRANSPORT AT THE CELLULAR LEVEL;

ANIMALS; BINDING SITES; BIOLOGICAL TRANSPORT; CERCOPITHECUS AETHIOPS; CITALOPRAM; COS CELLS; DNA MUTATIONAL ANALYSIS; HUMANS; MODELS, MOLECULAR; MUTATION; POINT MUTATION; PROTEIN CONFORMATION; REPRODUCIBILITY OF RESULTS; SEQUENCE HOMOLOGY, AMINO ACID; SEROTONIN; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS; SEROTONIN UPTAKE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 76249105122     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M109.072587     Document Type: Article

References (54)

1. Masson, J., Sagné, C., Hamon, M., and El Mestikawy, S. (1999) Pharmacol. Rev. 51, 439-464
2. Gether, U., Andersen, P. H., Larsson, O. M., and Schousboe, A. (2006) Trends Pharmacol. Sci. 27, 375-383
3. Rudnick, G. (2006) J. Membr. Biol. 213, 101-110
4. Chen, N. H., Reith, M. E., and Quick, M. W. (2004) Pflugers Arch. 447, 519-531
5. Moltzen, E. K., and Bang-Andersen, B. (2006) Curr. Top. Med. Chem. 6, 1801-1823
6. Andersen, J., Kristensen, A. S., Bang-Andersen, B., and Strømgaard, K. (2009) Chem. Commun. 3677-3692
7. Torres, G. E., Gainetdinov, R. R., and Caron, M. G. (2003) Nat. Rev. Neurosci. 4, 13-25
8. Apparsundaram, S., Stockdale, D. J., Henningsen, R. A., Milla, M. E., and Martin, R. S. (2008) J. Pharmacol. Exp. Ther. 327, 982-990
9. Rudnick, G. (2007) ACS Chem. Biol. 2, 606-609
10. Henry, L. K., Meiler, J., and Blakely, R. D. (2007) Mol. Interv. 7, 306-309
11. Barker, E. L., Moore, K. R., Rakhshan, F., and Blakely, R. D. (1999) J. Neurosci. 19, 4705-4717
12. Barker, E. L., Perlman, M. A., Adkins, E. M., Houlihan, W. J., Pristupa, Z. B., Niznik, H. B., and Blakely, R. D. (1998) J. Biol. Chem. 273, 19459-19468
13. Henry, L. K., Field, J. R., Adkins, E. M., Parnas, M. L., Vaughan, R. A., Zou, M. F., Newman, A. H., and Blakely, R. D. (2006) J. Biol. Chem. 281, 2012-2023
14. Kristensen, A. S., Larsen, M. B., Johnsen, L. B., and Wiborg, O. (2004) Eur. J. Neurosci. 19, 1513-1523
15. Larsen, M. B., Elfving, B., and Wiborg, O. (2004) J. Biol. Chem. 279, 42147-42156
16. Mortensen, O. V., Kristensen, A. S., and Wiborg, O. (2001) J. Neurochem. 79, 237-247
17. Andersen, J., Taboureau, O., Hansen, K. B., Olsen, L., Egebjerg, J., Strømgaard, K., and Kristensen, A. S. (2009) J. Biol. Chem. 284, 10276-10284
18. Ravna, A. W. (2006) World J. Biol. Psychiatry 7, 99-109
19. Ravna, A. W., and Edvardsen, O. (2001) J. Mol. Graphics Model. 20, 133-144
20. Ravna, A. W., Sylte, I., and Dahl, S. G. (2003) J. Pharmacol. Exp. Ther. 307, 34-41
21. Ravna, A. W., Sylte, I., Kristiansen, K., and Dahl, S. G. (2006) Bioorg. Med. Chem. 14, 666-675
22. Yamashita, A., Singh, S. K., Kawate, T., Jin, Y., and Gouaux, E. (2005) Nature 437, 215-223
23. Singh, S. K., Piscitelli, C. L., Yamashita, A., and Gouaux, E. (2008) Science 322, 1655-1661
24. Celik, L., Sinning, S., Severinsen, K., Hansen, C. G., Møller, M. S., Bols, M., Wiborg, O., and Schiøtt, B. (2008) J. Am. Chem. Soc. 130, 3853-3865
25. Forrest, L. R., Tavoulari, S., Zhang, Y. W., Rudnick, G., and Honig, B. (2007) Proc. Natl. Acad. Sci. U.S.A. 104, 12761-12766
26. Forrest, L. R., Zhang, Y. W., Jacobs, M. T., Gesmonde, J., Xie, L., Honig, B. H., and Rudnick, G. (2008) Proc. Natl. Acad. Sci. U.S.A. 105, 10338-10343
27. Zhang, Y. W., and Rudnick, G. (2006) J. Biol. Chem. 281, 36213-36220
28. Zhou, Y., Zomot, E., and Kanner, B. I. (2006) J. Biol. Chem. 281, 22092-22099
29. Zomot, E., Bendahan, A., Quick, M., Zhao, Y., Javitch, J. A., and Kanner, B. I. (2007) Nature 449, 726-730
30. Beuming, T., Kniazeff, J., Bergmann, M. L., Shi, L., Gracia, L., Raniszewska, K., Newman, A. H., Javitch, J. A., Weinstein, H., Gether, U., and Loland, C. J. (2008) Nat. Neurosci. 11, 780-789
31. Paczkowski, F. A., Sharpe, I. A., Dutertre, S., and Lewis, R. J. (2007) J. Biol. Chem. 282, 17837-17844
32. Wein, T., and Wanner, K. T. (2010) J. Mol. Model. 16, 155-161
33. Cheng, Y., and Prusoff, W. H. (1973) Biochem. Pharmacol. 22, 3099-3108
34. Sali, A., and Blundell, T. L. (1993) J. Mol. Biol. 234, 779-815
35. Beuming, T., Shi, L., Javitch, J. A., and Weinstein, H. (2006) Mol. Pharmacol. 70, 1630-1642
36. Laskowski, R. A., MacArthur, M. W., Moss, D. S., and Thornton, J. M. (1993) J. Appl. Crystallogr. 26, 283-291
37. Adkins, E. M., Barker, E. L., and Blakely, R. D. (2001) Mol. Pharmacol. 59, 514-523
38. Lin, F., Lester, H. A., and Mager, S. (1996) Biophys. J. 71, 3126-3135
39. Walline, C. C., Nichols, D. E., Carroll, F. I., and Barker, E. L. (2008) J. Pharmacol. Exp. Ther. 325, 791-800
40. Chen, J. G., Sachpatzidis, A., and Rudnick, G. (1997) J. Biol. Chem. 272, 28321-28327
41. Chen, J. G., and Rudnick, G. (2000) Proc. Natl. Acad. Sci. U.S.A. 97, 1044-1049
42. Kaufmann, K. W., Dawson, E. S., Henry, L. K., Field, J. R., Blakely, R. D., and Meiler, J. (2009) Proteins 74, 630-642
43. Jørgensen, A. M., Tagmose, L., Jørgensen, A. M., Topiol, S., Sabio, M., Gundertofte, K., Bøgesø, K. P., and Peters, G. H. (2007) ChemMedChem 2, 815-826
44. Hyttel, J., Bøgesø, K. P., Perregaard, J., and Sánchez, C. (1992) J. Neural Transm. Gen. Sect. 88, 157-160
45. Sánchez, C., Bergqvist, P. B., Brennum, L. T., Gupta, S., Hogg, S., Larsen, A., and Wiborg, O. (2003) Psychopharmacology 167, 353-362
46. Tavoulari, S., Forrest, L. R., and Rudnick, G. (2009) J. Neurosci. 29, 9635-9643
47. Henry, L. K., Defelice, L. J., and Blakely, R. D. (2006) Neuron 49, 791-796
48. Talvenheimo, J., Nelson, P. J., and Rudnick, G. (1979) J. Biol. Chem. 254, 4631-4635
49. Humphreys, C. J., Levin, J., and Rudnick, G. (1988) Mol. Pharmacol. 33, 657-663
50. Graham, D., Esnaud, H., Habert, E., and Langer, S. Z. (1989) Biochem. Pharmacol. 38, 3819-3826
51. Zhou, Z., Zhen, J., Karpowich, N. K., Law, C. J., Reith, M. E., and Wang, D. N. (2009) Nat. Struct. Mol. Biol. 16, 652-657
52. Zhou, Z., Zhen, J., Karpowich, N. K., Goetz, R. M., Law, C. J., Reith, M. E., and Wang, D. N. (2007) Science 317, 1390-1393
53. Singh, S. K., Yamashita, A., and Gouaux, E. (2007) Nature 448, 952-956
54. Jørgensen, A. M., Tagmose, L., Jørgensen, A. M., Bøgesø, K. P., and Peters, G. H. (2007) ChemMedChem 2, 827-840