Novel N-1,2-dihydroxypropyl analogs of lobelane inhibit vesicular monoamine transporter-2 function and methamphetamine-evoked dopamine release

Journal of Pharmacology and Experimental Therapeutics

Volumn 339, Issue 1, 2011, Pages 286-297

  Horton, David B ^a   Siripurapu, Kiran B ^a   Zheng, Guangrong ^a   Crooks, Peter A ^a   Dwoskin, Linda P ^a  

^a University of Kentucky   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2,6 DIPHENETHYLPIPERIDIN 1 YL)PROPANE 1,2 DIOL; 3 [2,6 DI(1 NAPHTHYLETHYL)PIPERIDIN 1 YL]PROPANE 1,2 DIOL; 3 [2,6 DI(2 METHOXYPHENETHYL)PIPERIDIN 1 YL]PROPANE 1,2 DIOL; 3 [2,6 DI(2,4 DICHLOROPHENETHYL)PIPERIDIN 1 YL]PROPANE 1,2 DIOL; 3 [2,6 DI(3 FLUOROPHENETHYL)PIPERIDIN 1 YL]PROPANE 1,2 DIOL; 3 [2,6 DI(3 METHOXYPHENETHYL)PIPERIDIN 1 YL]PROPANE 1,2 DIOL; 3 [2,6 DI(3,4 METHYLENEDIOXYPHENETHYL)PIPERIDIN 1 YL]PROPANE 1,2 DIOL; 3 [2,6 DI(4 BIPHENYLETHYL)PIPERIDIN 1 YL]PROPANE 1,2 DIOL; 3 [2,6 DI(4 METHOXYPHENETHYL)PIPERIDIN 1 YL]PROPANE 1,2 DIOL; DOPAMINE; GZ 252C; GZ 745A; GZ 745B; GZ 790A; GZ 790B; GZ 791A; GZ 791B; GZ 792A; GZ 792B; GZ 793A; GZ 793B; GZ 794A; GZ 794B; GZ 795A; GZ 795B; GZ 796A; GZ 796B; GZ 797A; GZ 797B; LOBELANE DERIVATIVE; LOBELINE; LOBELINE DERIVATIVE; METHAMPHETAMINE; SEROTONIN TRANSPORTER; UNCLASSIFIED DRUG; VESICULAR MONOAMINE TRANSPORTER 2;

ANIMAL TISSUE; ARTICLE; BRAIN SLICE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CORPUS STRIATUM; DOPAMINE RELEASE; DRUG POTENCY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; EVOKED RESPONSE; MALE; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION;

AMPHETAMINE-RELATED DISORDERS; ANIMALS; BINDING, COMPETITIVE; CORPUS STRIATUM; DATA INTERPRETATION, STATISTICAL; DOPAMINE; DOPAMINE UPTAKE INHIBITORS; KINETICS; LOBELINE; MALE; METHAMPHETAMINE; NICOTINIC AGONISTS; RATS; RATS, SPRAGUE-DAWLEY; SEROTONIN; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; SYNAPTIC VESICLES; SYNAPTOSOMES; VESICULAR MONOAMINE TRANSPORT PROTEINS;

EID: 80053161730     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.111.184770     Document Type: Article

References (40)

1. Beckmann JS, Denehy ED, Zheng G, Crooks PA, Dwoskin LP, and Bardo MT (2011) The effect of a novel VMAT2 inhibitor, GZ-793A, on methamphetamine reward in rats. Psychopharmacology, doi:10.1007/s00213-011-2488-9.
2. Beckmann JS, Siripurapu KB, Nickell JR, Horton DB, Denehy ED, Vartak A, Crooks PA, Dwoskin LP, and Bardo MT (2010) The novel pyrrolidine nor-lobelane analog UKCP-110 [cis-2,5-di-(2-phenethyl)-pyrrolidine hydrochloride] inhibits VMAT2 function, methamphetamine-evoked dopamine release, and methamphetamine self-administration in rats. J Pharmacol Exp Ther 335:841-851.
3. 125I]azidoiodoketanserin photoaffinity labeling of the monoamine transporter of platelet 5-HT organelles. Eur J Pharmacol 186:95-104.
4. Cheng Y and Prusoff WH (1973) Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol 22:3099-3108.
5. Crooks PA, Zheng G, Vartak AP, Culver JP, Zheng F, Horton DB, and Dwoskin LP (2010) Design, synthesis and interaction at the vesicular monoamine transporter-2 of lobeline analogs: potential pharmacotherapies for the treatment of psychostimulant abuse. Curr Top Med Chem 11:1103-1127.
6. Dar DE, Thiruvazhi M, Abraham P, Kitayama S, Kopajtic TA, Gamliel A, Slusher BS, Carroll FI, and Uhl GR (2005) Structure-activity relationship of trihexyphenidyl analogs with respect to the dopamine transporter in the on going search for a cocaine inhibitor. Eur J Med Chem 40:1013-1021. (Pubitemid 41421106)
7. Di Chiara G and Imperato A (1988) Drugs abused by humans preferentially increase synaptic dopamine concentrations in the mesolimbic system of freely moving rats. Proc Natl Acad Sci U S A 85:5274-5278.
8. Dwoskin LP and Crooks PA (2002) A novel mechanism of action and potential use for lobeline as a treatment for psychostimulant abuse. Biochem Pharmacol 63:89-98. (Pubitemid 34158807)
9. Fischer JF and Cho AK (1979) Chemical release of dopamine from striatal homogenates: evidence for an exchange diffusion model. J Pharmacol Exp Ther 208:203-209. (Pubitemid 9191709)
10. Gnegy ME (2003) The effect of phosphorylation on amphetamine-mediated outward transport. Eur J Pharmacol 479:83-91.
11. Grabowski J, Roache JD, Schmitz JM, Rhoades H, Creson D, and Korszun A (1997) Replacement medication of cocaine dependence: methylphenidate. J Clin Psychopharmacol 17:485-488. (Pubitemid 28389189)
12. Han DD and Gu HH (2006) Comparison of the monoamine transporters from human and mouse in their sensitivities to psychostimulant drugs. BMC Pharmacol 6:6.
13. Harrod SB, Dwoskin LP, Crooks PA, Klebaur JE, and Bardo MT (2001) Lobeline attenuates D-methamphetamine self-administration in rats. J Pharmacol Exp Ther 298:172-179. (Pubitemid 32574524)
14. Harrod SB, Dwoskin LP, Green TA, Gehrke BJ, and Bardo MT (2003) Lobeline does not serve as a reinforcer in rats. Psychopharmacology (Berl) 165:397-404. (Pubitemid 36223081)
15. Horton DB, Siripurapu KB, Norrholm SD, Culver JP, Hojahmat M, Beckmann JS, Harrod SB, Deaciuc AG, Bardo MT, Crooks PA, et al. (2011) meso-Transdiene analogs inhibit vesicular monoamine transporter-2 function and methamphetamine-evoked dopamine release. J Pharmacol Exp Ther 336:940-951.
16. Howell LL, Carroll FI, Votaw JR, Goodman MM, and Kimmel HL (2007) Effects of combined dopamine and serotonin transporter inhibitors on cocaine selfadministration in rhesus monkeys. J Pharmacol Exp Ther 320:757-765. (Pubitemid 46147957)
17. Institute of Laboratory Animal Resources (1996) Guide for the Care and Use of Laboratory Animals 7th ed. Institute of Laboratory Animal Resources, Commission on Life Sciences, National Research Council, Washington, DC.
18. Kilbourn M, Lee L, Vander Borght T, Jewett D, and Frey K (1995) Binding of α-dihydrotetrabenazine to the vesicular monoamine transporter is stereoselective. Eur J Pharmacol 278:249-252.
19. Lehéricy S, Brandel JP, Hirsch EC, Anglade P, Villares J, Scherman D, Duyckaerts C, Javoy-Agid F, and Agid Y (1994) Monoamine vesicular uptake sites in patients with Parkinson's disease and Alzheimer's disease, as measured by tritiated dihydrotetrabenazine autoradiography. Brain Res 659:1-9. (Pubitemid 24292838)
20. Liang NY and Rutledge CO (1982) Evidence for carrier-mediated efflux of dopamine from corpus striatum. Biochem Pharmacol 31:2479-2484. (Pubitemid 12095306)
21. Liu Y and Edwards RH (1997) The role of vesicular transport proteins in synaptic transmission and neural degeneration. Annu Rev Neurosci 20:125-156. (Pubitemid 27106378)
22. Miller DK, Crooks PA, Teng L, Witkin JM, Munzar P, Goldberg SR, Acri JB, and Dwoskin LP (2001) Lobeline inhibits the neurochemical and behavioral effects of amphetamine. J Pharmacol Exp Ther 296:1023-1034. (Pubitemid 32187378)
23. Miller DK, Crooks PA, Zheng G, Grinevich VP, Norrholm SD, and Dwoskin LP (2004) Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters. J Pharmacol Exp Ther 310:1035-1045. (Pubitemid 39108925)
24. Neugebauer NM, Harrod SB, Stairs DJ, Crooks PA, Dwoskin LP, and Bardo MT (2007) Lobelane decreases methamphetamine self-administration in rats. Eur J Pharmacol 571:33-38. (Pubitemid 47284051)
25. Nickell JR, Krishnamurthy S, Norrholm S, Deaciuc G, Siripurapu KB, Zheng G, Crooks PA, and Dwoskin LP (2010) Lobelane inhibits methamphetamine-evoked dopamine release via inhibition of the vesicular monoamine transporter-2. J Pharmacol Exp Ther 332:612-621.
26. Nickell JR, Zheng G, Deaciuc AG, Crooks PA, and Dwoskin LP (2011) Phenyl ring-substituted lobelane analogs: inhibition of [3H]dopamine uptake at the vesicular monoamine transporter-2. J Pharmacol Exp Ther 336:724-733.
27. Norrholm SD, Horton DB, and Dwoskin LP (2007) The promiscuity of the dopamine transporter: implications for the kinetic analysis of [3H]serotonin uptake in rat hippocampal and striatal synaptosomes. Neuropharmacology 53:982-989. (Pubitemid 350137397)
28. Owens MJ, Knight DL, and Nemeroff CB (2001) Second-generation SSRIs: human monoamine transporter binding profile of escitalopram and R-fluoxetine. Biol Psychiatry 50:345-350. (Pubitemid 32816947)
29. Pifl C, Drobny H, Reither H, Hornykiewicz O, and Singer EA (1995) Mechanism of the dopamine-releasing actions of amphetamine and cocaine: plasmalemmal dopamine transporter versus vesicular monoamine transporter. Mol Pharmacol 47:368-373.
30. Reith ME, Coffey LL, Xu C, and Chen NH (1994) GBR 12909 and 12935 block dopamine uptake into brain synaptic vesicles as well as nerve endings. Eur J Pharmacol 253:175-178. (Pubitemid 24063445)
31. Substance Abuse and Mental Health Services Administration, Office of Applied Studies (2008) Results from the 2007 National Survey on Drug Use and Health: National Findings, NSDUH Series H-34, DHHS Publication SMA 08-4343, Substance Abuse and Mental Health Services Administration, Rockville, MD.
32. Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, and Ewing A (1995) Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci 15:4102-4108.
33. Sulzer D and Rayport S (1990) Amphetamine and other psychostimulants reduce pH gradients in midbrain dopaminergic neurons and chromaffin granules: a mechanism of action. Neuron 5:797-808.
34. Sulzer D, Sonders MS, Poulsen NW, and Galli A (2005) Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol 75:406-433. (Pubitemid 40834286)
35. Tanda G, Newman AH, and Katz JL (2009) Discovery of drugs to treat cocaine dependence: behavioral and neurochemical effects of atypical dopamine transport inhibitors. Adv Pharmacol 57:253-289.
36. Teng L, Crooks PA, and Dwoskin LP (1998) Lobeline displaces [3H]dihydrotetrabenazine binding and releases [3H]dopamine from rat striatal synaptic vesicles: comparison with D-amphetamine. J Neurochem 71:258-265. (Pubitemid 28292557)
37. 3H]dopamine: differential inhibition of synaptosomal and vesicular [3H]dopamine uptake. J Pharmacol Exp Ther 280:1432-1444.
38. Wise RA and Bozarth MA (1987) A psychomotor stimulant theory of addiction. Psychol Rev 94:469-492.
39. Zheng G, Dwoskin LP, Deaciuc AG, Norrholm SD, and Crooks PA (2005a) Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter. J Med Chem 48:5551-5560. (Pubitemid 41209253)
40. Zheng G, Dwoskin LP, Deaciuc AG, Zhu J, Jones MD, and Crooks PA (2005b) Lobelane analogues as novel ligands for the vesicular monoamine transporter-Bioorg Med Chem 13:3899-3909. (Pubitemid 40725023)