Characterization of the cocaine binding site on the sigma-1 receptor

Biochemistry

Volumn 46, Issue 11, 2007, Pages 3532-3542

  Chen, Yuenmu ^a   Hajipour, Abdol R ^b   Sievert, Michael K ^a   Arbabian, Marty ^a   Ruoho, Arnold E ^a  

^a UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

^b ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

COCAINE PHOTOAFFINITY; GUINEA PIG LIVER; PHOTOLABELING; SIGMA-1 RECEPTOR;

BINDING SITES; BIOCHEMISTRY; DERIVATIVES; HORMONES; PEPTIDES; PROTEINS;

DRUG PRODUCTS;

3 IODO 4 AZIDOCOCAINE; COCAINE; COCAINE DERIVATIVE; CYANOGEN BROMIDE; PHENYL GROUP; SIGMA 1 OPIATE RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING SITE; CARBOXY TERMINAL SEQUENCE; CELL STRAIN COS7; DIPOLE; ELECTRON; GUINEA PIG; LIVER; NONHUMAN; PHOTOAFFINITY LABELING; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN PURIFICATION; RECEPTOR BINDING;

AFFINITY LABELS; AMINO ACID SEQUENCE; ANIMALS; ASPARTIC ACID; BINDING SITES; BLOTTING, WESTERN; CERCOPITHECUS AETHIOPS; COCAINE; COS CELLS; GUINEA PIGS; MICROSOMES, LIVER; MOLECULAR SEQUENCE DATA; RECEPTORS, SIGMA; SEQUENCE ALIGNMENT;

CAVIA;

EID: 33947416579     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi061727o     Document Type: Article

References (70)

1. Martin, W. R., Eades, C. G., Thompson, J. A., Huppler, R. E., and Gilbert, P. E. (1976) The effects of morphine- and nalorphine-like drugs in the nondependent and morphine-dependent chronic spinal dog, J. Pharmacol. Exp. Ther. 197, 517-532.
2. Zukin, S. R., Brady, K. T., Slifer, B. L., and Balster, R. L. (1984) Behavioral and biochemical stereoselectivity of sigma opiate/PCP receptors, Brain Res. 294, 174-177.
3. Vaupel, D. B. (1983) Naltrexone fails to antagonize the sigma effects of PCP and SKF 10,047 in the dog, Eur. J. Pharmacol. 92, 269-274.
4. Tam, S. W. (1983) Naloxone-inaccessible sigma receptor in rat central nervous system, Proc. Natl. Acad. Sci. U.S.A. 80, 6703-6707.
5. 3H]- haloperidol binding in guinea pig brain membranes, Proc. Natl. Acad. Sci. U.S.A. 81, 5618-5621.
6. + channels by sigma receptors expressed in Xenopus oocytes, Biophys. J. 78, 98A.
7. Aydar, E., Palmer, C. P., Klyachko, V. A., and Jackson, M. B. (2002) The sigma receptor as a ligand-regulated auxiliary potassium channel subunit, Neuron 34, 399-410.
8. + channel modulation in rodent neurohypophysial nerve terminals by sigma receptors and not by dopamine receptors, J. Physiol. (London) 517, 391-406.
9. Wilke, R. A., Mehta, R. P., Lupardus, P. J., Chen, Y., Ruoho, A. E., and Jackson, M. B. (1999) Sigma receptor photolabeling and sigma receptor-mediated modulation of potassium channels in tumor cells, J. Biol. Chem. 214, 18387-18392.
10. Hayashi, T., Maurice, T., and Su, T. P. (2000) Ca(2+) signaling via sigma(1)-receptors: novel regulatory mechanism affecting intracellular Ca(2+) concentration, J. Pharmacol. Exp. Ther. 293, 788-798.
11. Hayashi, T., and Su, T. P. (2004) Sigma-1 receptors at galactosylceramide-enriched lipid microdomains regulate oligodendrocyte differentiation, Proc. Natl. Acad. Sci. U.S.A. 101, 14949-14954.
12. Matsuno, K., Matsunaga, K., Senda, T., and Mita, S. (1993) Increase in extracellular acetylcholine level by sigma ligands in rat frontal cortex, J. Pharmacol. Exp. Ther. 265, 851-859.
13. Lysko, P. G., Gagnon, R. C., Yue, T. L., Gu, J. L., and Feuerstein, G. (1992) Neuroprotective effects of SKF 10,047 in cultured rat cerebellar neurons and in gerbil global brain ischemia, Stroke 23, 414-419.
14. Contreras, P. C., Ragan, D. M., Bremer, M. E., Lanthorn, T. H., Gray, N. M., Iyengar, S., Jacobson, A. E., Rice, K. C., and de Costa, B. R. (1991) Evaluation of U-50,488H analogs for neuroprotective activity in the gerbil, Brain Res. 546, 79-82.
15. Pontecorvo, M. J., Karbon, E. W., Goode, S., Clissold, D. B., Borosky, S. A., Patch, R. J., and Ferkany, J. W. (1991) Possible cerebroprotective and in vivo NMDA antagonist activities of sigma agents, Brain Res. Bull. 26, 461-465.
16. Casellas, P., Bourrie, B., Canat, X., Carayon, P., Buisson, I., Paul, R., Breliere, J. C., and Le, Fur, G. (1994) Immunopharmacological profile of SR 31747: in vitro and in vivo studies on humoral and cellular responses, J. Neuroimmunol. 52, 193-203.
17. Morio, Y., Tanimoto, H., Yakushiji, T., and Morimoto, Y. (1994) Characterization of the currents induced by sigma ligands in NCB20 neuroblastoma cells, Brain Res. 637, 190-196.
18. Soriani, O., Foil, F. L., Roman, F., Monnet, F. P., Vaudry, H., and Cazin, L. (1999) A-Current down-modulated by sigma receptor in frog pituitary melanotrope cells through a G protein-dependent pathway, J. Pharmacol. Exp. Ther. 289, 321-328.
19. Soriani, O., Vaudry, H., Mei, Y. A., Roman, F., and Cazin, L. (1998) Sigma ligands stimulate the electrical activity of frog pituitary melanotrope cells through a G-protein-dependent inhibition of potassium conductances, J. Pharmacol. Exp. Ther. 286, 163-171.
20. Wu, X. Z., Bell, J. A., Spivak, C. E., London, E. D., and Su, T. P. (1991) Electrophysiological and binding studies on intact NCB-20 cells suggest presence of a low affinity sigma receptor, J. Pharmacol. Exp. Ther. 257, 351-359.
21. Menkel, M., Terry, P., Pontecorvo, M., Katz, J. L., and Witkin, J. M. (1991) Selective sigma ligands block stimulant effects of cocaine, Eur. J. Pharmacol. 201, 251-252.
22. Witkin, J. M., Terry, P., Menkel, M., Hickey, P., Pontecorvo, M., Ferkany, J., and Katz, J. L. (1993) Effects of the selective sigma receptor ligand, 6-[6-(4-hydroxypiperidinyl)hexyloxy]-3-methylflavone (NPC 16377), on behavioral and toxic effects of cocaine, J. Pharmacol. Exp. Ther. 266, 473-482.
23. McCracken, K. A., Bowen, W. D., de Costa, B. R., and Matsumoto, R. R. (1999) Two novel sigma receptor ligands, BD1047 and LR172, attenuate cocaine-induced toxicity and locomotor activity, Eur. J. Pharmacol. 370, 225-232.
24. McCracken, K. A., Bowen, W. D., and Matsumoto, R. R. (1999) Novel sigma receptor ligands attenuate the locomotor stimulatory effects of cocaine, Eur. J. Pharmacol. 365, 35-38.
25. Skuza, G. (1999) Effect of sigma ligands on the cocaine-induced convulsions in mice, Pol. J. Pharmacol. 51, 477-483.
26. Langa, F., Codony, X., Tovar, V., Lavado, A., Gimenez, E., Cozar, P., Cantero, M., Dordal, A., Hernandez, E., Perez, R., Monroy, X., Zamanillo, D., Guitart, X., and Montoliu, L. (2003) Generation and phenotypic analysis of sigma receptor type I (sigma 1) knockout mice, Eur. J. Neurosci. 18, 2188-2196.
27. Cendan, C. M., Pujalte, J. M., Portillo-Salido, E., Montoliu, L., and Baeyens, J. M. (2005) Formalin-induced pain is reduced in sigma(1) receptor knockout mice, Eur. J. Pharmacol. 511, 73-74.
28. Crawford, K. W., Coop, A., and Bowen, W. D. (2002) sigma(2) Receptors regulate changes in sphingolipid levels in breast tumor cells, Eur. J. Pharmacol. 443, 207-209.
29. Vilner, B. J., and Bowen, W. D. (2000) Modulation of cellular calcium by sigma-2 receptors: release from intracellular stores in human SK-N-SH neuroblastoma cells, J. Pharmacol. Exp. Ther. 292, 900-911.
30. Hanner, M., Moebius, F. F., Flandorfer, A., Knaus, H. G., Striessnig, J., Kempner, E., and Glossmann, H. (1996) Purification, molecular cloning, and expression of the mammalian sigmal-binding site, Proc. Natl. Acad. Sci. U.S.A. 93, 8072-8077.
31. Kekuda, R., Prasad, P. D., Fei, Y. J., Leibach, F. H., and Ganapathy, V. (1996) Cloning and functional expression of the human type 1 sigma receptor (hSigmaR1), Biochem. Biophys. Res. Commun. 229, 553-558.
32. Seth, P., Fei, Y. J., Li, H. W., Huang, W., Leibach, F. H., and Ganapathy, V. (1998) Cloning and functional characterization of a sigma receptor from rat brain, J. Neurochem. 70, 922-931.
33. Seth, P., Leibach, F. H., and Ganapathy, V. (1997) Cloning and structural analysis of the cDNA and the gene encoding the murine type 1 sigma receptor, Biochem. Biophys. Res. Commun. 241, 535-540.
34. Jbilo, O., Vidal, H., Paul, R., De Nys, N., Bensaid, M., Silve, S., Carayon, P., Davi, D., Galiegue, S., Bourrie, B., Guillemot, J. C., Ferrara, P., Loison, G., Maffrand, J. P., Le Fur, G., and Casellas, P. (1997) Purification and characterization of the human SR 31747A-binding protein. A nuclear membrane protein related to yeast sterol isomerase, J. Biol. Chem. 272, 27107-27115.
35. Moebius, F. F., Striessnig, J., and Glossmann, H. (1997) The mysteries of sigma receptors: new family members reveal a role in cholesterol synthesis, Trends Pharmacol. Sci. 18, 67-70.
36. Uchida, N., Ujike, H., Tanaka, Y., Sakai, A., Yamamoto, M., Fujisawa, Y., Kanzaki, A., and Kuroda, S. (2005) A variant of the sigma receptor type-1 gene is a protective factor for Alzheimer disease, Am. J. Geriatr. Psychiatry 13, 1062-1066.
37. Ujike, H., Kuroda, S., and Otsuki, S. (1996) Sigma receptor antagonists block the development of sensitization to cocaine, Eur. J. Pharmacol. 296, 123-128.
38. Sharkey, J., Glen, K. A., Wolfe, S., and Kuhar, M. J. (1988) Cocaine binding at sigma receptors, Eur. J. Pharmacol. 149, 171-174.
39. Nguyen, E. C., McCracken, K. A., Liu, Y., Pouw, B., and Matsumoto, R. R. (2005) Involvement of sigma (sigma) receptors in the acute actions of methamphetamine: receptor binding and behavioral studies, Neuropharmacology 49, 638-645.
40. Stefanski, R., Justinova, Z., Hayashi, T., Takebayashi, M., Goldberg, S. R., and Su, T. P. (2004) Sigma1 receptor upregulation after chronic methamphetamine self-administration in rats: a study with yoked controls, Psychopharmacology (Berlin) 175, 68-75.
41. Takahashi, S., Miwa, T., and Horikomi, K. (2000) Involvement of sigma 1 receptors in methamphetamine-induced behavioral sensitization in rats, Neurosci. Lett. 289, 21-24.
42. Resek, J. F., and Ruoho, A. E. (1988) Photoaffinity labeling the beta-adrenergic receptor with an iodoazido derivative of norepinephrine, J. Biol. Chem. 263, 14410-14416.
43. Ruoho, A. E., Rashidbaigi, A., and Roeder, P. E. (1984) in Membranes, Detergents, and Receptor Solubilization, pp 119-160, Alan R. Liss, New York.
44. 125I]2-N-[(3′- iodo-4′-azidophenyl)-propionyl]tetrabenazine binding sites for the synaptic vesicle monoamine transporter, J. Biol. Chem. 272, 26049-26055.
45. Sievert, M. K., Resek, I. F., Wu, Z., Rong, Y., and Ruoho, A. E. (2000) UV crosslinking of adrenergic receptors and ligands. Detection by SDS-PAGE, Methods Mol. Biol. 126, 315-327.
46. +, a photoactivatable probe for G-protein structure: evidence for holotransducin oligomers in which the ADP-ribosylated carboxyl terminus of alpha interacts with both alpha and gamma subunits, Proc. Natl. Acad. Sci. U.S.A. 87, 3645-3649.
47. Liu, Y., Arshavsky, V. Y., and Ruoho, A. E. (1996) Interaction sites of the COOH-terminal region of the gamma subunit of cGMP phosphodiesterase with the GTP-bound alpha subunit of transducin, J. Biol. Chem. 271, 26900-26907.
48. 125I)iodoazidococaine, a photoaffinity label for the haloperidol-sensitive sigma receptor, Proc. Natl. Acad. Sci. U.S.A. 89, 1393-1397.
49. 3H]phenyl)guanidine, Proc. Natl. Acad. Sci. U.S.A. 85, 2844-2848.
50. Moebius, F. F., Burrows, G. G., Hanner, M., Schmid, E., Striessnig, J., and Glossmann, H. (1993) Identification of a 27-kDa high affinity phenylalkylamine-binding polypeptide as the sigma 1 binding site by photoaffinity labeling and ligand-directed antibodies, Mol. Pharmacol. 44, 966-971.
51. Martin, T. F. (1989) Cell cracking: permeabilizing cells to macromolecular probes, Methods Enzymol. 168, 225-233.
52. Matsudaira, P. (1987) Sequence from picomole quantities of proteins electroblotted onto polyvinylidene difluoride membranes, J. Biol. Chem. 262, 10035-10038.
53. Laemmli, U. K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4, Nature 227, 680-685.
54. Schagger, H., and von Jagow, G. (1987) Tricine-sodium dodecyl sulfate-polyacrylamide gel electrophoresis for the separation of proteins in the range from 1 to 100 kDa, Anal. Biochem. 166, 368-379.
55. Hajipour, A. R., Arbabian, M., and Ruoho, A. E. (2002) Tetramethylammonium dichloroiodate: An efficient and environmentally friendly iodination reagent for iodination of aromatic compounds under mild and solvent-free conditions, J. Org. Chem. 67, 8622-8624.
56. Moebius, F. F., Reiter, R. J., Hanner, M., and Glossmann, H. (1997) High affinity of sigma 1-binding sites for sterol isomerization inhibitors: evidence for a pharmacological relationship with the yeast sterol C8-C7 isomerase, Br. J. Pharmacol. 121, 1-6.
57. Mans, D. M., and Pearson, W. H. (2004) Total synthesis of (+)-cocaine via desymmetrization of a meso-dialdehyde, Org. Lett. 6, 3305-3308.
58. Lee, J. C., Lee, K., and Cha, J. K. (2000) Enantioselective synthesis of unnatural (S)-(+)-cocaine, J. Org. Chem. 65, 4773-4775.
59. Lin, R. H., Castells, J., and Rapoport, H. (1998) Enantiospecific synthesis of natural (-)-cocaine and unnatural (+)-cocaine from D- and L-glutamic acid, J. Org. Chem. 63, 4069-4078.
60. Lieske, S. F., Yang, B., Eldefrawi, M. E., MacKerell, A. D., and Wright, J. (1998) (-)-3 beta-substituted ecgonine methyl esters as inhibitors for cocaine binding and dopamine uptake, J. Med. Chem. 41, 864-876.
61. Chang, A. C., Burgess, J. P., Mascarella, S. W., Abraham, P., Kuhar, M. J., and Carroll, F. I. (1997) Synthesis and transporter binding properties of 2,3-diphenyltropane stereoisomers. Comparison to 3 beta-phenyltropane-2 beta-carboxylic acid esters, J. Med. Chem. 40, 1247-1251.
62. Kelkar, S. V., Izenwasser, S., Katz, J. L., Klein, C. L., Zhu, N. J., and Trudell, M. L. (1994) Synthesis, cocaine receptor affinity, and dopamine uptake inhibition of several new 2-beta-substituted 3-beta-phenyltropanes, J. Med. Chem. 37, 3875-3877.
63. Davies, H. M. L., Saikali, E., Huby, N. J. S., Gilliatt, V. J., Matasi, J. J., Sexton, T., and Childers, S. R. (1994) Synthesis of 2-beta-acyl-3-beta- aryl-8-azabicyclo[3.2.1]octanes and their binding affinities at dopamine and serotonin transport sites in rat striatum and-frontal cortex, J. Med. Chem. 37, 1262-1268.
64. Carroll, F. I., Gray, J. L., Abraham, P., Kuzemko, M. A., Lewin, A. H., Boja, J. W., and Kuhar, M. J. (1993) 3-Aryl-2-(3′-substituted-1′, 2′,4′-oxadiazol-5′-yl)tropane analogs of cocaine-affinities at the cocaine binding-site at the dopamine, serotonin, and norepinephrine transporters, J. Med. Chem. 36, 2886-2890.
65. Yu, D. W., Galley, S. J., Wolf, A. P., Macgregor, R. R., Dewey, S. L., Fowler, J. S., and Schlyer, D. J. (1992) Synthesis of C-11 labeled iodinated cocaine derivatives and their distribution in baboon brain measured using positron emission tomography, J. Med. Chem. 35, 2178-2183.
66. Carroll, F. I., Lewin, A. H., Boja, J. W., and Kuhar, M. J. (1992) Cocaine receptor-biochemical-characterization and structure-activity- relationships of cocaine analogs at the dopamine transporter, J. Med. Chem. 35, 969-981.
67. Ablordeppey, S. Y., Fischer, J. B., and Glennon, R. A. (2000) Is a nitrogen atom an important pharmacophoric element in sigma ligand binding? Bioorg. Med. Chem. 8, 2105-2111.
68. Moebius, F. F., Bermoser, K., Reiter, R. J., Hanner, M., and Glossmann, H. (1996) Yeast sterol C8-C7 isomerase: identification and characterization of a high-affinity binding site for enzyme inhibitors, Biochemistry 35, 16871-16878.
69. Ganapathy, M. E., Prasad, P. D., Huang, W., Seth, P., Leibach, F. H., and Ganapathy, V. (1999) Molecular and ligand-binding characterization of the sigma-receptor in the Jurkat human T lymphocyte cell line, J. Pharmacol. Exp. Ther. 289, 251-260.
70. Seth, P., Ganapathy, M. E., Conway, S. J., Bridges, C. D., Smith, S. B., Casellas, P., and Ganapathy, V. (2001) Expression pattern of the type 1 sigma receptor in the brain and identity of critical anionic amino acid residues in the ligand-binding domain of the receptor, Biochim. Biophys. Acta 1540, 59-67.