The sigma1 receptor interacts with N-alkyl amines and endogenous sphingolipids

European Journal of Pharmacology

Volumn 609, Issue 1-3, 2009, Pages 19-26

  Ramachandran, Subramaniam ^a   Chu, Uyen B ^a   Mavlyutov, Timur A ^a   Pal, Arindam ^a   Pyne, Susan ^b   Ruoho, Arnold E ^a  

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

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Alkyl amine; Endogenous ligand; Ligand binding; Sigma1 receptor; Sphingolipid

Indexed keywords

PENTAZOCINE; SIGMA 1 OPIATE RECEPTOR; SIGMA 2 OPIATE RECEPTOR; SPHINGANINE; SPHINGOLIPID; SPHINGOSINE; SPHINGOSINE 1 PHOSPHATE; SPHINGOSINE KINASE 1;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; ENZYME ACTIVITY; LIGAND BINDING; NONHUMAN; PRIORITY JOURNAL; RAT; RECEPTOR BINDING;

AMINES; ANIMALS; BINDING, COMPETITIVE; CARRIER PROTEINS; CELL LINE; DRUG INTERACTIONS; EPITOPES; ESCHERICHIA COLI; GUINEA PIGS; HISTIDINE; HUMANS; INHIBITORY CONCENTRATION 50; KIDNEY; KINETICS; LIGANDS; LIVER; MEMBRANES; MOLECULAR STRUCTURE; PENTAZOCINE; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR); RADIOLIGAND ASSAY; RATS; RECEPTORS, SIGMA; SPHINGOLIPIDS; SPHINGOSINE;

EID: 64549104571     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2009.03.003     Document Type: Article

References (40)

1. Ablordeppey S.Y., Fischer J.B., and Glennon R.A. Is a nitrogen atom an important pharmacophoric element in sigma ligand binding?. Bioorg. Med. Chem 8 (2000) 2105-2111
2. Aydar E., Palmer C.P., Klyachko V.A., and Jackson M.B. The sigma receptor as a ligand-regulated auxiliary potassium channel subunit. Neuron 34 (2002) 399-410
3. Bruns R.F., Lawson-Wendling K., and Pugsley T.A. A rapid filtration assay for soluble receptors using polyethylenimine-treated filters. Anal. Biochem 132 (1983) 74-81
4. Chen Y., Hajipour A.R., Sievert M.K., Arbabian M., and Ruoho A.E. Characterization of the cocaine binding site on the sigma-1 receptor. Biochemistry 46 (2007) 3532-3542
5. Cheng Y., and Prusoff W.H. Relationship between the inhibition constant (KI) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem. Pharmacol 22 (1973) 3099-3108
6. Chun J., Goetzl E.J., Hla T., Igarashi Y., Lynch K.R., Moolenaar W., Pyne S., and Tigyi G. International Union of Pharmacology. XXXIV. Lysophospholipid receptor nomenclature. Pharmacol. Rev 54 (2002) 265-269
7. Crawford K.W., and Bowen W.D. Sigma-2 receptor agonists activate a novel apoptotic pathway and potentiate antineoplastic drugs in breast tumor cell lines. Cancer Res 62 (2002) 313-322
8. Fontanilla D., Johannessen M., Hajipour A.R., Cozzi N.V., Jackson M.B., and Ruoho A.E. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science 323 (2009) 934-937
9. Gebreselassie D., and Bowen W.D. Sigma-2 receptors are specifically localized to lipid rafts in rat liver membranes. Eur. J. Pharmacol 493 (2004) 19-28
10. Glennon R.A. Pharmacophore identification for sigma-1 (sigma1) receptor binding: application of the "deconstruction-reconstruction-elaboration" approach. Mini. Rev. Med. Chem 5 (2005) 927-940
11. Hanner M., Moebius F.F., Flandorfer A., Knaus H.G., Striessnig J., Kempner E., and Glossmann H. Purification, molecular cloning, and expression of the mammalian sigma1-binding site. Proc. Natl. Acad. Sci. U. S. A 93 (1996) 8072-8077
12. Hannun Y.A., and Obeid L.M. Principles of bioactive lipid signalling: lessons from sphingolipids. Nat. Rev. Mol. Cell. Biol 9 (2008) 139-150
13. Hayashi T., and Su T.P. Regulating ankyrin dynamics: roles of sigma-1 receptors. Proc. Natl. Acad. Sci. U. S. A 98 (2001) 491-496
14. Hayashi T., and Su T.P. Intracellular dynamics of sigma-1 receptors (sigma(1) binding sites) in NG108-15 cells. J. Pharmacol. Exp. Ther 306 (2003) 726-733
15. Hayashi T., and Su T.P. Sigma-1 receptors (sigma(1) binding sites) form raft-like microdomains and target lipid droplets on the endoplasmic reticulum: roles in endoplasmic reticulum lipid compartmentalization and export. J. Pharmacol. Exp. Ther 306 (2003) 718-725
16. Hayashi T., and Su T.P. Sigma-1 receptor ligands: potential in the treatment of neuropsychiatric disorders. CNS Drugs 18 (2004) 269-284
17. Hayashi T., and Su T.P. Sigma-1 receptors at galactosylceramide-enriched lipid microdomains regulate oligodendrocyte differentiation. Proc. Natl. Acad. Sci. U. S. A 101 (2004) 14949-14954
18. Hayashi T., and Su T.P. Sigma-1 receptor chaperones at the ER- mitochondrion interface regulate Ca(2+) signaling and cell survival. Cell 131 (2007) 596-610
19. Hellewell S.B., Bruce A., Feinstein G., Orringer J., Williams W., and Bowen W.D. Rat liver and kidney contain high densities of sigma 1 and sigma 2 receptors: characterization by ligand binding and photoaffinity labeling. Eur. J. Pharmacol. 268 (1994) 9-18
20. Igarashi Y., Hakomori S., Toyokuni T., Dean B., Fujita S., Sugimoto M., Ogawa T., el-Ghendy K., and Racker E. Effect of chemically well-defined sphingosine and its N-methyl derivatives on protein kinase C and src kinase activities. Biochemistry 28 (1989) 6796-6800
21. Kahoun J.R., and Ruoho A.E. (125I)iodoazidococaine, a photoaffinity label for the haloperidol-sensitive sigma receptor. Proc. Natl. Acad. Sci. U. S. A. 89 (1992) 1393-1397
22. Kohama T., Olivera A., Edsall L., Nagiec M.M., Dickson R., and Spiegel S. Molecular cloning and functional characterization of murine sphingosine kinase. J. Biol. Chem 273 (1998) 23722-23728
23. Kumagai K., Shono K., Nakayama H., Ohno Y., and Saji I. (2R-trans)-2-butyl-5-heptylpyrrolidine as a potent sigma receptor ligand produced by Streptomyces longispororuber. J. Antibiot. (Tokyo) 53 (2000) 467-473
24. Laggner C., Schieferer C., Fiechtner B., Poles G., Hoffmann R.D., Glossmann H., Langer T., and Moebius F.F. Discovery of high-affinity ligands of sigma1 receptor, ERG2, and emopamil binding protein by pharmacophore modeling and virtual screening. J. Med. Chem 48 (2005) 4754-4764
25. Matsumoto R.R., Bowen W.D., Tom M.A., Vo V.N., Truong D.D., and De Costa B.R. Characterization of two novel sigma receptor ligands: antidystonic effects in rats suggest sigma receptor antagonism. Eur. J. Pharmacol 280 (1995) 301-310
26. Moebius F.F., Reiter R.J., Hanner M., and Glossmann H. 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 (1997) 1-6
27. Pal A., Hajipour A.R., Fontanilla D., Ramachandran S., Chu U.B., Mavlyutov T., and Ruoho A.E. Identification of regions of the sigma-1 receptor ligand binding site using a novel photoprobe. Mol. Pharmacol 72 (2007) 921-933
28. Palmer C.P., Mahen R., Schnell E., Djamgoz M.B., and Aydar E. Sigma-1 receptors bind cholesterol and remodel lipid rafts in breast cancer cell lines. Cancer Res 67 (2007) 11166-11175
29. Ramachandran S., Lu H., Prabhu U., and Ruoho A.E. Purification and characterization of the guinea pig sigma-1 receptor functionally expressed in Escherichia coli. Protein. Expr. Purif 51 (2007) 283-292
30. Renaudo A., L'Hoste S., Guizouarn H., Borgese F., and Soriani O. Cancer cell cycle modulated by a functional coupling between sigma-1 receptors and Cl- channels. J. Biol. Chem 282 (2007) 2259-2267
31. Sakano S., Takemura H., Yamada K., Imoto K., Kaneko M., and Ohshika H. Ca2+ mobilizing action of sphingosine in Jurkat human leukemia T cells. Evidence that sphingosine releases Ca2+ from inositol trisphosphate- and phosphatidic acid-sensitive intracellular stores through a mechanism independent of inositol trisphosphate. J. Biol. Chem 271 (1996) 11148-11155
32. Spiegel S., and Milstien S. Sphingosine-1-phosphate: an enigmatic signalling lipid. Nat. Rev. Mol. Cell. Biol 4 (2003) 397-407
33. Spiegel S., and Milstien S. Functions of the multifaceted family of sphingosine kinases and some close relatives. J. Biol. Chem 282 (2007) 2125-2129
34. Takebayashi M., Hayashi T., and Su T.P. Nerve growth factor-induced neurite sprouting in PC12 cells involves sigma-1 receptors: implications for antidepressants. J. Pharmacol. Exp. Ther 303 (2002) 1227-1237
35. Thiriot D.S., Sievert M.K., and Ruoho A.E. Identification of human vesicle monoamine transporter (VMAT2) lumenal cysteines that form an intramolecular disulfide bond. Biochemistry 41 (2002) 6346-6353
36. Vilner B.J., John C.S., and Bowen W.D. Sigma-1 and sigma-2 receptors are expressed in a wide variety of human and rodent tumor cell lines. Cancer Res 55 (1995) 408-413
37. Waters C.M., Long J., Gorshkova I., Fujiwara Y., Connell M., Belmonte K.E., Tigyi G., Natarajan V., Pyne S., and Pyne N.J. Cell migration activated by platelet-derived growth factor receptor is blocked by an inverse agonist of the sphingosine 1-phosphate receptor-1. Faseb J 20 (2006) 509-511
38. Wu Z., and Bowen W.D. Role of sigma-1 receptor C-terminal segment in inositol 1,4,5-trisphosphate receptor activation: constitutive enhancement of calcium signaling in MCF-7 tumor cells. J. Biol. Chem 283 (2008) 28198-28215
39. Yagasaki Y., Numakawa T., Kumamaru E., Hayashi T., Su T.P., and Kunugi H. Chronic antidepressants potentiate via sigma-1 receptors the brain-derived neurotrophic factor-induced signaling for glutamate release. J. Biol. Chem 281 (2006) 12941-12949
40. Zhang H., and Cuevas J. Sigma receptors inhibit high-voltage-activated calcium channels in rat sympathetic and parasympathetic neurons. J. Neurophysiol 87 (2002) 2867-2879