Dual probes for the dopamine transporter and σ1 receptors: Novel piperazinyl alkyl-bis(4′-fluorophenyl)amine analogues as potential cocaine-abuse therapeutic agents

Journal of Medicinal Chemistry

Volumn 46, Issue 13, 2003, Pages 2589-2598

  Cao, Jianjing ^a   Kulkarni, Santosh S ^a   Husbands, Stephen M ^a,d   Bowen, Wayne D ^b   Williams, Wanda ^b   Kopajtic, Theresa ^a   Katz, Jonathan L ^a   George, Clifford ^c   Newman, Amy Hauck ^a  

^a NATIONAL INSTITUTE ON DRUG ABUSE   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

^c NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^d University of Bath   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYLCYCLOHEXANECARBOXYLIC ACID 2 MORPHOLINOETHYL ESTER; [3 (3,5 DIMETHYL 1 PIPERAZINYL)PROPYL] N,N BIS(4 FLUOROPHENYL)AMINE; [3 (4 BENZYL 1 PIPERAZINYL)PROPYL] N,N BIS(4 FLUOROPHENYL)AMINE HYDROBROMIDE; [3 [4 (3 HYDROXY 3 PHENYLPROPYL) 1 PIPERAZINYL]PROPYL] N,N BIS(4 FLUOROPHENYL)AMINE; ANILINE DERIVATIVE; CARAMIPHEN; COCAINE; DOPAMINE TRANSPORTER; DOPAMINE UPTAKE INHIBITOR; NORADRENALIN TRANSPORTER; OPIATE ANTAGONIST; PENTOXYVERINE; PIPERAZINYLBIS(4' FLUOROPHENYL)AMINE DERIVATIVE; PRECLAMOL; RIMCAZOLE; SEROTONIN TRANSPORTER; SIGMA 1 OPIATE RECEPTOR; UNCLASSIFIED DRUG; VANOXERINE;

ANALYTIC METHOD; ARTICLE; BINDING AFFINITY; COCAINE DEPENDENCE; COMPARATIVE MOLECULAR FIELD ANALYSIS; DISCRIMINATIVE STIMULUS; DRUG DEPENDENCE TREATMENT; DRUG DESIGN; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; DUAL PROBE; MOLECULAR MODEL; MOLECULAR PROBE; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING, COMPETITIVE; BRAIN; COCAINE-RELATED DISORDERS; CRYSTALLOGRAPHY, X-RAY; DOPAMINE; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; MEMBRANE GLYCOPROTEINS; MEMBRANE TRANSPORT PROTEINS; MODELS, MOLECULAR; NERVE TISSUE PROTEINS; PIPERAZINES; RADIOLIGAND ASSAY; RATS; RECEPTORS, SIGMA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037777740     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030008u     Document Type: Article

References (29)

1. Kreek, M. J.; LaForge, S.; Butelman, E. Pharmacotherapy of Addiction. Nature Rev. Drug Discovery 2002, 1, 710-736.
2. Newman, A. H. Novel Pharmacotherapies for Cocaine Abuse 1997-2000. Exp. Opin. Ther. Pat. 2000, 10, 1095-1122.
3. Newman, A. H.; Kulkarni, S. S. Probes for the Dopamine Transporter: New leads toward a Cocaine-Abuse Therapeutic - A focus on analogues of benztropine and rimcazole. Med. Res. Rev. 2002, 22, 1-36.
4. 1) antagonists represent a new strategy against cocaine addiction and toxicity. Neurosci. Biobehav. Rev. 2002, 26, 499-527.
5. 1 receptor in cocaine-induced conditioned place preference: Possible dependence on dopamine uptake blockade. Neuropsychopharmacology 2002, 26, 444-455.
6. 1 receptor in the cocaine-induced conditioned place preference. NeuroReport 2000, 11, 2885-2888.
7. Ferris, R. M.; Tang, F. L. M.; Chang, K.-J.; Russell, A. Evidence that the Potential Antipsychotic Agent Rimcazole (BW 234U) is a Specific Competitive Antagonist of Sigma Sites in Brain. Life Sci. 1986, 38, 2329-2337.
8. Menkel, M.; Terry, P.; Katz, J. L.; Witkin, J. M. Selective σ ligands Block Stimulant Effects of Cocaine. Eur. J. Pharmacol. 1991, 201, 251-252.
9. Matsumoto, R. R.; Hewett, K. L.; Pouw, B.; Husbands, S. M.; Cao, J. J.; Newman, A. H. Rimcazole analogues attenuate the convulsive effects of cocaine: correlation with binding to sigma receptors rather than dopamine transporters. Neuropharmacology 2001, 41, 878-886.
10. Izenwasser, S.; Newman, A. H.; Katz, J. L. Cocaine and sigma ligands inhibit dopamine uptake via a common low affinity site in the rat caudate-putamen. Eur. J. Pharmacol. 1993, 243, 201-205.
11. Husbands, S. H.; Kopajtic, T.; Izenwasser, S.; Bowen, W. D.; Vilner, B. J.; Katz, J. L. Newman, A. H. Structure - Activity Relationships at the Monoamine Transporters and σ Receptors for a Novel Series of 9-[3-cis-3,5-Dimethyl-1-piperazinyl)propyl] carbazole (Rimcazole) Analogues. J. Med. Chem. 1999, 42, 4446-4455.
12. Matecka, D.; Rothman, R. B.; Radesca, L.; deCosta, B. R.; Dersch, C. M.; Partilla, J. S.; Pert, A.; Glowa, J. R.; Wojnicki, F. H. E.; Rice, K. C. Development of Novel, Potent and Selective Dopamine Reuptake Inhibitors through Alteration of the Piperazine Ring of the 1-[2-(Diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)methoxy] ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909). J. Med. Chem. 1996, 39, 4704-4716.
13. Prisinzano, T.; Greiner, E.; Johnson, E. M., II; Dersch, C. M.; Marcus, J.; Partilla, J. S.; Rothman, R. B.; Jacobson, A. E.; Rice, K. C. Piperidine Analogues of 1- [2- [Bis(4-fluorophenyl)methoxy]- ethyl]-4-(3-phenylpropyl)piperazine (GBR 12909): High Affinity Ligands for the Dopamine Transporter. J. Med. Chem. 2002, 45, 4371-4374.
14. Dutta, A. K.; Xu, C.; Reith, M. E. A. Structure - Activity Relationship Studies of Novel 4-[2-[Bis(4-fluorophenyl)methoxyl- ethyl]-1-(3-phenylpropyl)piperidine Analogues: Synthesis and Biological Evaluation at the Dopamine and Serotonin Transporter Sites. J. Med. Chem. 1996, 39, 749-756.
15. Dutta, A. K.; Fei, X. S.; Beardsley, P. M.; Newman, J. L.; Reith, M. E. A. Structure-Activity Relationship studies of 4-[2-diphenylmethoxy)ethyl-1-benzylpiperidine derivatives and their N-analogues: Evaluation of behavioral activity of O- and N- analogues and their binding to monoamine transporters. J. Med. Chem. 2001, 44, 937-948.
16. Dutta, A. K.; Davis, M. C.; Fei, X.-S.; Beardsley, P. M.; Cook, C. D.; Reith, M. E. A. Expansion of Structure - Activity Studies of Piperidine Analogues of 1-[2-(Diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine (GBR 12935) Compounds by Altering Substitutions in the N-Benzyl Moiety and Behavioral Pharmacology of Selected Molecules. J. Med. Chem. 2002, 45, 654-662.
17. Katz, J. L.; Libby, T.; Kopajtic, T.; Husbands, S. M.; Newman, A. H. Behavioral Effects of Rimcazole Analogues Alone and in Combination with Cocaine. Eur. J. Pharmacol. 2003, 61262, 1-11.
18. Cao, J.; Husbands, S. M.; Kopajtic, T.; Katz, J. L. Newman, A. H. [3-cis-3,5-Dimethyl-1-piperazinyl)alkyl]-bis-(4′-fluorophenyl)-amine Analogues as Novel Probes for the Dopamine Transporter. Bioorg Med. Chem. Lett. 2001, 11, 3169-3173.
19. Lewis, D. B.; Matecka, D.; Zhang, Y.; Hsin, L.-W.; Dersch, C. M.; Stafford, D.; Glowa, J. R.; Rothman, R. B.; Rice, K. C. Oxygenated Analogues of 1- [2-bis(4-fluorophenyl)methoxy]ethyl]- 4-(3-phenylpropyl)piperazine) GBR 12935 and GBR 12909) as Potential Extended-Action Cocaine-Abuse Therapeutics. J. Med. Chem. 1999, 42, 5029-5042.
20. Hsin, L.-W.; Dersch, C. M.; Baumann, M. H.; Stafford, D.; Glowa, J. R.; Rothman, R. B.; Jacobson, A. E.; Rice, K. C. Development of long-acting dopamine transporter ligands as potential cocaine-abuse therapeutic agents: Chiral hydroxyl-containing derivatives of 1-[2-bis(4-fluorophenyl)methoxyl]ethyl]-4-(3-phenylpropyl)- piperazine and 1-[2-diphenylmethoxy)ethyl]-4-(3-propylphenyl)- piperazine. J. Med. Chem. 2002, 45, 1321-1329.
21. Glennon, R. A.; Ablordeppey, S. Y.; Ismaiel, A. M.; El-Ashmawy, M. B.; Fischer, J. B.; Howie, K. B. Structural Features Important for σ Receptor Binding. J. Med. Chem. 1994, 37, 1214-1219.
22. Ablordeppey, S. Y.; Fischer, J. B.; Glennon, R. A. Is a Nitrogen Atom an Important Pharmacophoric Element in Sigma Ligand Binding? Bioorg. Med. Chem. 2000, 8, 2105-2111.
23. Ablordeppey, S. Y.; El-Ashmawy, M.; Fischer, J. B.; Glennon, R. A. A CoMFA Investigation of Sigma Receptor Binding Affinity: Reexamination of a Spurious Sigma Ligand. Eur. J. Med. Chem. 1998, 33, 625-633.
24. 1 Receptor Ligands. J. Med. Chem. 2001, 44, 4404-4415.
25. Glennon, R. A.; Yousif, M. Y.; Ismaiel, A. M.; El-Ashmawy, M. B.; Herndon, J. L.; Fischer, J. B.; Server, A. C.; Howie, K. J. B. Novel 1-Phenylpiperazine and 4-Phenylpiperidine Derivatives as High-Affinity σ Ligands. J. Med. Chem. 1991, 34, 3360-3365.
26. Cairi, M.; Gerig, J. T. Dynamics at the active site of bis (4-fluorophenyl)carbamoyl-α-chymotrypsin. J. Am. Chem. Soc. 1983, 105, 4793-4800.
27. Bruker 1995 SMART and SAINT Data Collection and Reduction Software for the SMART system. Bruker-AXS, Madison, WI.
28. Sheldrick, G. M. 1997. SHELXTL Version 5.1 Bruker Analytical X-ray Instruments, Madison, WI.
29. Newman, A. H.; Robarge, M. J.; Howard, I. M.; Wittkopp, S. L.; Kopajtic, T.; Izenwasser, S.; Katz, J. L. Structure-Activity Relationships at the Monoamine Transporters and Muscarinic Receptors for N-substituted-3α-[3′-Cl-,4′-Cl-,4′,4″-diCl- substituted)diphenyl]methoxytropanes. J. Med. Chem. 2001, 44, 633-640.