Modeling of the pH dependence of the binding of WIN 35,428 to the dopamine transporter in rat striatal membranes: Is the bioactive form positively charged or neutral?

Journal of Pharmacology and Experimental Therapeutics

Volumn 278, Issue 3, 1996, Pages 1340-1348

  Xu, Cen ^a   Reith, Maarten E A ^b  

^a ILLINOIS STATE UNIVERSITY   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 (BENZHYDRYLOXY)ETHYL] 4 (3 PHENYLPROPYL)PIPERAZINE; 3BETA (4 FLUOROPHENYL) 2BETA TROPANECARBOXYLIC ACID METHYL ESTER; BENZOCAINE; COCAINE; DOPAMINE TRANSPORTER; TROPARIL;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BRAIN SYNAPTOSOME; CONTROLLED STUDY; CORPUS STRIATUM; DOPAMINE UPTAKE; DRUG RECEPTOR BINDING; LIGAND BINDING; MALE; NONHUMAN; PH; PKA; PRIORITY JOURNAL; RAT;

ANIMALS; BENZOCAINE; BINDING, COMPETITIVE; CARRIER PROTEINS; CATIONS; COCAINE; CORPUS STRIATUM; DOPAMINE; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; DOPAMINE UPTAKE INHIBITORS; HYDROGEN-ION CONCENTRATION; KINETICS; LIGANDS; MALE; MEMBRANE GLYCOPROTEINS; MEMBRANE TRANSPORT PROTEINS; NERVE TISSUE PROTEINS; RATS; RATS, SPRAGUE-DAWLEY; SYNAPTOSOMES;

EID: 0030426646     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (52)

1. ABRAHAM, P., PITNER, J. B., LEWIN, A. H., BOJA, J. W., KUHAR, M. J. AND CARROLL, F. I.: N-modified analogues of cocaine: synthesis and inhibition of binding to the cocaine receptor. J. Med. Chem. 35: 141-144, 1992.
2. 3H]WIN-35,428 binding in the caudate nucleus of the rabbit: Evidence for a single site on the dopamine transporter. J. Pharmacol. Exp. Ther. 273: 435-444, 1995.
3. AMARA, S. G. AND KUHAR, M. J.: Neurotransmitter transporters: recent progress. Annu. Rev. Neurosci. 16: 73-93, 1993.
4. 3H]GBR 12935 binding in vitro to rat striatal membranes: labeling of the dopamine uptake complex. J. Neurochem. 48: 1887-1896, 1987.
5. BERGMAN, J., MADRAS, B. K., JOHNSON, S. E. AND SPEALMAN, R. D.: Effects of cocaine and related drugs in nonhuman primates. III. Self-administration by squirrel monkeys. J. Pharmacol. Exp. Ther. 251: 150-155, 1989.
6. 3H]mazindol. J. Pharmacol. Exp. Ther. 253: 1206-1214, 1990.
7. 3H] cocaine in striatum and its relationship to the dopamine transporter. Membr. Biochem. 7: 87-106, 1987a.
8. CALLIGARO, D. O. AND ELDEFRAWI, M. E.: Central and peripheral cocaine receptors. J. Pharmacol. Exp. Ther. 243: 61-68, 1987b.
9. CARROLL, F. I., ABRAHAM, P., LEWIN, A. H., PARHAM, K. A., BOJA, J. W. AND KUHAR, M.: Isopropyl and phenyl esters of 3β-(4-substituted phenyl)tropan-2β-carboxylic acids. Potent and selective compounds for the dopamine transporter. J. Med. Chem. 35: 2497-2500, 1992a.
10. CARROLL, F. I., KOTIAN, P., DEHGHANI, A., GRAY, J. L., KUZEMKO, M. A., PARHAM, K. A., ABRAHAM, P., LEWIN, A. H., BOJA, J. W. AND KUHAR, M. J.: Cocaine and 3 beta-(4′-substituted phenyl)tropane-2 beta-carboxylic acid ester and amide analogues. New high-affinity and selective compounds for the dopamine transporter. J. Med. Chem. 38: 379-388, 1995.
11. CARROLL, F. I., LEWIN, A. H., BOJA, J. W. AND KUHAR, M. J.: Cocaine receptor: Biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter. J. Med. Chem. 35: 969-981, 1992b.
12. CARROLL, F. I., MASCARELLA, S. W., KUZEMKO, M. A., GAO, Y., ABRAHAM, P., LEWIN, A. H., BOJA, J. W. AND KUHAR, M. J.: Synthesis, ligand binding, and QSAR (CoMFA and classical) study of 3β-(3′-substituted phenyl)-, 3β-(4′-substituted phenyl)-, and 3β-(3′,4′-disubstitutedphenyl)tropane-2β carboxylic acid methyl esters. J. Med. Chem. 37: 2865-2873, 1994.
13. 50) of an enzymatic reaction. Biochem. Pharmacol. 22: 3099-3108, 1973.
14. 3H]WIN-35,428 binding to the dopamine uptake carrier. I. Effect of tonicity and buffer composition. J. Neurosci. Methods 51: 23-30, 1994.
15. COURTNEY, K. R. AND STRICHARTZ, G. R.: Structural elements which determine local anesthetic activity. In Handbook of Experimental Pharmacology, vol. 81, ed. by G. R. Strichartz, pp. 53-94, Springer-Verlag, New York, NY, 1987.
16. DARCHEN, F., SCHERMAN, D., DESNOS, C. AND HENRY, J. P.: Characteristics of the transport of the quaternary ammonium 1-methyl-4-phenylpyridinium by chromaffin granules. Biochem. Pharmacol. 37: 4381-4387, 1988.
17. DAVIES, H. M., SAIKALI, E., SEXTON, T. AND CHILDERS, S. R.: Novel 2-substituted cocaine analogs: binding properties at dopamine transport sites in rat striatum. Eur. J. Pharmacol. 244: 93-97, 1993.
18. DELEAN, A., MUNSON, P. J. AND RODBARD, D.: Simultaneous analysis of families of sigmoidal curves: Application to bioassay, radioligand assay, and physiological dose-response curves. Am. J. Physiol. 235: E97-102, 1978.
19. EDVARDSEN, O. AND DAHL, S. G.: A putative model of the dopamine transporter. Mol. Brain Res. 27: 265-274, 1994.
20. ESHLEMAN, A. J., NEVE, R. L., JANOWSKY, A. AND NEVE, K. A.: Characterization of a recombinant human dopamine transporter in multiple cell lines. J. Pharmacol. Exp. Ther. 274: 276-283, 1995.
21. FIBIGER, H. C., PHILLIPS, A. G. AND BROWN, E. E.: The neurobiology of cocaine-induced reinforcement. Ciba. Found. Symp. 166: 96-111; discussion 111-, 1992.
22. GATLEY, S. J., YU, D. W., FOWLER, J. S., MACGREGOR, R. R., SCHLYER, D. J., DEWEY, S. L., WOLF, A. P., MARTIN, T., SHEA, C. E. AND VOLKOW, N. D.: Studies with differentially labeled [11C]cocaine, [11C]norcocaine, [11C]benzoylecgonine, and [11C]- and 4′-[18F]fluorococaine to probe the extent to which [11C]cocaine metabolites contribute to PET images of the baboon brain. J. Neurochem. 62: 1154-1162, 1994.
23. GIROS, B., WANG, Y. M., SUTER, S., MCLESKEY, S. B., PIFL, C. AND CARON, M. G.: Delineation of discrete domains for substrate, cocaine, and tricyclic antidepressant interactions using chimeric dopamine-norepinephrine transporters. J. Biol. Chem. 269: 15986-15988, 1994.
24. HENRY, J. P. AND SCHERMAN, D.: Radioligands of the vesicular monoamine transporter and their use as markers of monoamine storage vesicles. Biochem. Pharmacol. 38: 2395-2404, 1989.
25. HILLE, B.: Ionic Channels of Excitable Membranes, pp. 272-303, Sinauer Associates Inc., Sunderland, MA, 1984.
26. KATZUNG, B. G.: Introduction. In Basic and Clinical Pharmacology, ed. by B. G. Katzung, pp. 1-8, Appleton & Lange, Norwalk, CT, 1995.
27. KELKAR, S. V., IZENWASSER, S., KATZ, J. L., KLEIN, C. L., ZHU, N. AND TRUDELL, M. L.: Synthesis, cocaine receptor affinity, and dopamine uptake inhibition of several new 2β-substituted 3β-phenyltropanes. J. Med. Chem. 37: 3875-3877, 1994.
28. 3H]WIN-35,428 is an artifact of freezing caudate tissue. Life Sci. 50: PL139-42, 1992.
29. KITAYAMA, S., SHIMADA, S., XU, H., MARKHAM, L., DONOVAN, D. M. AND UHL, G. R.: Dopamine transporter site-directed mutations differentially alter substrate transport and cocaine binding. Proc. Natl. Acad. Sci. U.S.A. 89: 7782-7785, 1992.
30. KOTIAN, P., ABRAHAM, P., LEWIN, A. H., MASCARELLA, S. W., BOJA, J. W., KUHAR, M. J. AND CARROLL, F. I.: Synthesis and ligand binding study of 3β-(4′-substituted phenyl)-2β-(heterocyclic)tropanes. J. Med. Chem. 38: 3451-3453, 1995.
31. KOZIKOWSKI, A. P., SAIAH, M. K., BERGMANN, J. S. AND JOHNSON, K. M.: Structure-activity relationship studies of N-sulfonyl analogs of cocaine: role of ionic interaction in cocaine binding. J. Med. Chem. 37: 3440-3442, 1994.
32. LEWIN, A. H., GAO, Y. G., ABRAHAM, P., BOJA, J. W., KUHAR, M. J. AND CARROLL, F. I.: 2β-Substituted analogues of cocaine. Synthesis and inhibition of binding to the cocaine receptor. J. Med. Chem. 35: 135-140, 1992.
33. 3H]Cocaine binding sites in caudate-putamen. J. Pharmacol. Exp. Ther. 251: 131-141, 1989.
34. MOTULSKY, H. J AND MAHAN, L. C.: The kinetics of competitive radioligand binding predicted by the law of mass action. Mol. Pharmacol. 25: 1-9, 1984.
35. MUNSON, P. J. AND RODBARD, D.: Ligand: A versatile computerized approach for characterization of ligand-binding systems. Anal. Biochem. 107: 220-239, 1980.
36. + channels. Cocaine vs. quaternary compounds. Biophys. J. 58: 95-106, 1990.
37. 3H]GBR 12,935 binding. Mol. Pharmacol. 45: 125-135, 1994.
38. 3H]tropane to the dopamine uptake carrier. J. Neurochem. 61: 167-177, 1993.
39. 3H]WIN-35,428 binding to the dopamine uptake carrier. II. Effect of membrane fractionation procedure and freezing. J. Neurosci. Methods 51: 31-38, 1994.
40. REITH, M. E. A., DE COSTA, B., RICE, K. C. AND JACOBSON, A. E.: Evidence for mutually exclusive binding of cocaine, BTCP, GBR 12935, and dopamine to the dopamine transporter. Eur. J. Pharmacol. 227: 417-425, 1992.
41. REITH, M. E. A. AND LAJTHA, A.: Locomotor depression in mice by norcocaine does not involve central α2-adrenergic or presynaptic dopamine receptors. Pharmacol. Biochem. Behav. 24: 305-307, 1986.
42. REITH, M. E. A., MEISLER, B. E., SEHSHEN, H. AND LAJTHA, A.: Structural requirements for cocaine congeners to interact with dopamine and serotonin uptake sites in mouse brain and to induce stereotyped behavior. Biochem. Pharmacol. 35: 1123-1129, 1986.
43. RITCHIE, J. M. AND GREENGARD, P.: On the mode of action of local anesthetics. Annu. Rev. Pharmacol. 6: 405-430, 1966.
44. RITCHIE, J. M. AND RITCHIE, B. R.: Local anesthetics: effect of pH on activity. Science 162: 1394-1395, 1968.
45. RITZ, M. C., LAMB, R. J., GOLDBERG, S. R. AND KUHAR, M. J.: Cocaine receptors on dopamine transporters are related to self-administration of cocaine. Science 237: 1219-1223, 1987.
46. RITZ, M. C., CONE, E. J. AND KUHAR, M. J.: Cocaine inhibition of ligand binding at dopamine, norepinephrine and serotonin transporters: a structure-activity study. Life Sci. 46: 635-645, 1990.
47. ROTHMAN, R. B., CADET, J. L., AKUNNE, H. C., SILVERTHORN, M. L., BAUMANN, M. H., CARROLL, F. I., RICE, K. C., DE COSTA, B. R., PARTILLA, J. S. AND WANG, J. B.: Studies of the biogenic amine transporters. IV. Demonstration of a multiplicity of binding sites in rat caudate membranes for the cocaine analog [125I]RTI-55. J. Pharmacol. Exp. Ther. 270: 296-309, 1994.
48. ROUFFIAC, R., LATTES, A. AND VALDIGUE, P.: Determination of ionization constants by paper chromatography. Ann. Pharmac. Francaises 21: 413-422, 1963.
49. SHIMADA, S., KITAYAMA, S., LIN, C. L., PATEL, A., NANTHAKUMAR, E., GREGOR, P., KUHAR, M. AND UHL, G.: Cloning and expression of a cocaine-sensitive dopamine transporter complementary DNA [published erratum appears in Science 1992 Mar 6;255:1195]. Science 254: 576-578, 1991.
50. SKOU, J. C.: Local anaesthetics. III. Distribution of local anaesthetics between the solid phase 1 aqueous phase of peripheral nerves. Acta Pharmacol. Toxicol. 10: 297-304, 1954.
51. SRIVASTAVA, S. AND CRIPPEN, G. M.: Analysis of cocaine receptor site ligand binding by three-dimensional Voronoi site modeling approach. J. Med. Chem. 38: 3572-3579, 1993.
52. YANG, B., WRIGHT, J., ELDEFRAWI, M. E., POU, S. AND MACKERELL, A. D., JR.: Conformational, aqueous solvation, and pka contributions to the binding and activity of cocaine, WIN 32,065-2, and the WIN Vinyl Analog. J. Am. Chem. Soc. 116: 8722-8732, 1994.