Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors

British Journal of Pharmacology

Volumn 146, Issue 1, 2005, Pages 15-24

  Exley, Richard ^a   Iturriaga Vásquez, Patricio ^b   Lukas, Ronald J ^c   Sher, Emanuele ^d   Cassels, Bruce K ^b   Bermudez, Isabel ^a  

^a OXFORD BROOKES UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF CHILE   (Chile)

^c BARROW NEUROLOGICAL INSTITUTE   (United States)

^d ELI LILLY AND COMPANY   (United States)

Author keywords

Armepavine; Laudanosine; Nicotinic acetylcholine receptors; Tetrandrine; Xenopus oocytes

Indexed keywords

7 O BENZYL N METHYLCOCLAURINE; 7 O BENZYL N, 12 O DIMETHYL COCLAURINE; ALPHA 4 BETA 2 NICOTINIC ACETYLCHOLINE RECEPTOR; ALPHA 4 BETA 4 NICOTINIC ACETYLCHOLINE RECEPTOR; ALPHA 7 NICOTINIC ACETYLCHOLINE RECEPTOR; ARMEPAVINE; BENZYLTETRAHYDROISOQUINOLINE; COCLAURINE; LAUDANOSINE; NICOTINIC RECEPTOR; RADIOLIGAND; RECOMBINANT RECEPTOR; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CELL CLONE; CONTROLLED STUDY; DRUG EFFECT; DRUG INHIBITION; DRUG MECHANISM; ELECTROPHYSIOLOGY; HUMAN; LIGAND BINDING; LIPOPHILICITY; NONHUMAN; OOCYTE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; VOLTAGE CLAMP; XENOPUS;

ANIMALS; BINDING, COMPETITIVE; CELL LINE; HUMANS; LIGANDS; OOCYTES; PATCH-CLAMP TECHNIQUES; RECEPTORS, NICOTINIC; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROISOQUINOLINES; XENOPUS LAEVIS;

EID: 30644458311     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1038/sj.bjp.0706307     Document Type: Article

References (20)

1. ASTLES, P.C., BAKER, R.S., BOOT, J.R., BROAD, L.M., DELL, C.P. & KEENAN, M. (2002). Recent progress in the development of subtype selective nicotinic acetylcholine receptor ligands. Curr. Drug Targets - CNS Neurol. Disord, 1, 337-348.
2. BERTRAND, D., BALLIVET, M. & RUNGGER, D. (1990). Activation and blocking of neuronal nicotinic acetylcholine receptor reconstituted in Xenopus oocytes. Proc. Natl. Acad. Sci. U.S.A., 87, 1993-1997.
3. BUCK, K.T. (1987). Bisbenzylisoquinolines. In: The Alkaloids, ed. Brossi, A. pp. 1-222. New York: Academic Press.
4. BUISSON, B. & BERTRAND, D. (2001). Chronic exposure to nicotine upregulates the human α4β2 nicotinic acetylcholine receptor function. J. Neurosci., 21, 1819-1829.
5. CACHELIN, A.B. & RUST, G. (1994). Unusual pharmacology of (+)-tubocurarine with rat neuronal nicotinic acetylcholine receptors containing β4 subunits. Mol. Pharmacol., 46, 1168-1174.
6. CHAVEZ-NORIEGA, L.E., CRONA, J.H., WASHBURN, M.S., URRUTIA, A., ELLIOT, K. & JOHNSON, B.C. (1997). Pharmacological characterization of recombinant human neuronal nicotinic acetylcholine receptors hα2β2, hα2β4, hα3β2, hα3β4, hα4β2, hα4β4 and hα7 expressed in Xenopus oocytes. J. Pharmacol. Exp. Ther., 280, 346-356.
7. CHIODINI, F., CHARPANTIER, E., MULLER, D., TASSANYI, E., FUCHS-BUCLER, T. & BERTRAND, D. (2001). Blockade and activation of the human neuronal nicotinic acetylcholine receptors by atracurium and laudanosine. Anesthesiology, 94, 643-651.
8. CODDING, P.W. & JAMES, M.N.G. (1973). The crystal structure of a potent neuromuscular blocking agent: d-tubocurarine dichloride pentahydrate. Acta. Crystallogr., 29, 935-942.
9. EATON, J.B., KUO, Y.-P., FUH, L.P.-T., KRISHNAN, C., STEINLEIN, O., LINDSTROM, J.M. & LUKAS, R.J. (2000). Properties of stably and heterologously-expressed human α4β4-nicotinic acetylcholine receptors (nAChR). Soc. Neurosci. Abst., 26, 371.
10. EATON, J.B., PENG, J.-H., SCHROEDER, K.M., GEORGE, A.A., FRYER, J.D., KRISHNAN, C., BUHLMAN, L., KUO, Y.-P., STEINLEIN, O. & LUKAS, R.J. (2003). Characterization of human α4β2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells. Mol. Pharmacol., 64, 1283-1294.
11. FELIX, J.P., KING, V.F., SHEVELL, J.L., GARCIA, M.L., KACZOROWSKI, G.J., BICK, I.R.C. & SLAUGHTER, R.S. (1992). Bis(benzylisoquinoline) analogs of tetrandrine block L-type calcium channels: evidence for interaction at the diltiazem-binding site. Biochemistry, 31, 11793-11800.
12. GARLAND, C.M., FOREMAN, R.C., CHAD, J.E., HOLDEN-DYE, L. & WALKER, R. (1998). The actions of muscle relaxants at nicotinic acetylcholine receptor isoforms. Eur. J. Pharmacol., 357, 83-92.
13. HOULIHAN, L.M., SLATER, Y., GUERRA, D.L., PENG, J.-H., KUO, Y.-P., LUKAS, R.J., CASSELS, B.K. & BERMUDEZ, I. (2001). Activity of cytisine and its brominated isosteres on recombinant human α7, α4β2 and α4β4 nicotinic acetylcholine receptors. J. Neurochem., 78, 1029-1043.
14. ITURRIAGA-VÁSQUEZ, P., MIQUEL, R., IVORRA, M.D., D'OCON, M.P. & CASSELS, B.K. (2003). Simplified tetrandrine congeners as possible antihypertensive agents with a dual mechanism of action. J. Nat. Prod., 66, 954-957.
15. KING, V.F., GARCIA, M.L., HIMMEL, D., REUBEN, J.P., LAM, Y.T., PAN, J., HAN, G. & KACZOROWSKI, G.J. (1988). Interaction of tetrandrine with slowly inactivating calcium channels. J. Biol. Chem., 263, 2238-2244.
16. LIPSCOMBE, D. & RANG, H.P. (1987). Nicotinic receptors of frog ganglia resemble pharmacologically those of skeletal muscle. J. Neurosci., 8, 3258-3265.
17. NOONEY, J.M., PETERS, J.A. & LAMBER, J.J. (1992). A patch clamp study of the nicotinic acetylcholine receptor of bovine chromaffin cells in culture. J. Physiol., 455, 503-527.
18. SLATER, E.Y., HOULIHAN, L.M., CASSELS, B.K., LUKAS, R.J. & BERMUDEZ, I. (2002). Effects of the plant alkaloid tetrandrine on human nicotinic acetylcholine receptors. Eur. J. Pharmacol., 450, 213-221.
19. WANG, Z.G. & LIU, G.Z. (1985). Advances in natural products in China. TIPS, 6, 423-425.
20. ZWART, R. & VIJVERBERG, H.P.M. (1998). Four pharmacologically distinct subtypes of α4β2 nicotinic receptors expressed in Xenopus oocytes. Mol. Pharmacol., 54, 1124-1131.