Vesicular monoamine transporter 2: Role as a novel target for drug development (original) (raw)

• Yelin R, Schuldiner S. Vesicular neurotransmitter transporters: pharmacology, biochemistry, and molecular analysis. In: Reith MEA, ed Neurotransmitter Transporters: Structure, Function, and Regulation 2nd Totowa, NJ: Humana Press; 2002:313–354.
  Google Scholar
• Erickson JD, Eiden LE, Hoffiman BJ. Expression cloning of a reserpine-sensitive vesicular monoamine transporter. Proc Natl Acad Sci USA. 1992;89:10993–10997.
  PubMed CAS Google Scholar
• Lin Y, Peter D, Roghani A, et al. A cDNA that suppresses MPP+ toxicity encodes a vesicular amine transporter. Cell. 1992;70:539–551.
  Google Scholar
• Erickson J, Eiden L. Functional identification and molecular cloning of a human brain vesicle monoamine transporter. J Neurochem. 1993, 61:2314–2317.
  PubMed CAS Google Scholar
• Erickson JD, Schaefer MKH, Bonner TI, Eiden LE, Weihe E. Distinct pharmacological properties and distribution in neurons and endocrine cells of two isoforms of the human vesicular monoamine transporter. Proc Natl Acad Sci USA. 1996;93:5166–5171.
  PubMed CAS Google Scholar
• Peter D, Liu Y, Sternini C, de Giorgio R, Brecha N, Edwards RH. Differential expression of two vesicular monoamine transporters. J Neurosci. 1995;15:6179–6188.
  PubMed CAS Google Scholar
• Weihe E, Schafer MK, Erickson JD, Eiden LE. Localization of vesicular monoamine transporter isoforms (VMAT1 and VMAT2) to endocrine cells and neurons in rat. J Mol Neurosci. 1994;5:149–164.
  PubMed CAS Google Scholar
• Hansson SR, Mezey E, Hoffman BJ. Ontogeny of vesicular monoamine transporter mRNAs VMAT1 and VMAT2, II: expression in neural creast derivatives and their target sites in the rat. Brain Res Dev Brain Res. 1998;110:159–174.
  PubMed CAS Google Scholar
• Peter D, Jimenez J, Lin Y, Kim J, Edwards RH. The chromaffin granule and synaptic vesicle amine transporters differ in substrate recognition and sensitivity to inhibitors. J Biol Chem. 1994;269:7231–7237.
  PubMed CAS Google Scholar
• Pletscher A. Effect of neuroleptics and other drugs on monoamine uptake by membranes of adrenal chromaffin granules. Br J Pharmacol. 1977;59:419–424.
  PubMed CAS Google Scholar
• Scherman D, Henry JP. Reserpine binding to bovine chromaffin granule membranes. Mol Pharmacol. 1984;25:113–122.
  PubMed CAS Google Scholar
• Darchen F, Scherman D, Henry JP. Reserpine binding to chromaffin granules suggests the existence of two conformations of the monoamine transporter. Biochemistry. 1989;28:1692–1697.
  PubMed CAS Google Scholar
• Henry JP, Scherman D. Radioligands of the vesicular monoamine transporter and their use as markers of monoamine storage vesicles. Biochem Pharmacol. 1989;38:2395–2404.
  PubMed CAS Google Scholar
• Scherman D, Jaudon P, Henry JP. Characterization of the monoamine carrier of chromaffin granule membrane by binding of [2–3H]dihydrotetrabenazine. Proc Natl Acad Sci USA. 1983;80:584–588.
  PubMed CAS Google Scholar
• Cohen G, Kesler N. Monoamine oxidase and mitochondrial respiration. J Neurochem. 1999;73:2310–2315.
  PubMed CAS Google Scholar
• Lin Y, Edwards RH. The role of vesicular transport proteins in synaptic transmission and neural degeneration. Annu Rev Neurosci. 1997;20:125–156.
  CAS Google Scholar
• Langston JW. The etiology of Parkinson's disease with emphasis on the MPTP story. Neurology, 1996;47:S153-S160.
  PubMed CAS Google Scholar
• Snyder SH, D'Amato RJ. MPTP: a neurotoxin relevant to the pathophysiology of Parkinson's disease. Neurology. 1986:36:250–258.
  PubMed CAS Google Scholar
• Jenner P, Schapira AHV, Marsden CD. New insights into the cause of Parkinson's disease. Neurology. 1992;42:2241–2250.
  PubMed CAS Google Scholar
• Jenner P, Dexter DT, Sian J, Schapira AHV, Marsden CD. Oxidative stress as a cause of nigral cell death in Parkinson's disease and incidental Lewy body disease. Ann Neurol. 1992;32:S82-S87.
  PubMed CAS Google Scholar
• German DC, Sonsalla PK. A role for the vesicular monoamine transporter (VMAT2) in Parkinson's disease. Adv Behav Biol. 2003;54:131–137.
  CAS Google Scholar
• Adams JD, Jr, Chang ML, Klaidman L. Parkinson's disease—redox mechanisms. Curr Med Chem. 2001;8:809–814.
  PubMed CAS Google Scholar
• Scherman D, Darchen F, Desnos C, Henry JP. 1-Methyl-4-phenylpyridinium is a substrate of the vesicular monoamine uptake system of chromaffin granules. Eur J Pharmacol. 1988:146:359–360.
  PubMed CAS Google Scholar
• Daniels AJ, Jr, Reinhard JF, Jr. Energy-driven uptake of the neurotoxin 1-methyl-4-phenylpyridine into chromaffin granules via the catecholamine transporter. J Biol Chem. 1988;263:5034–5036.
  PubMed CAS Google Scholar
• Darchen F, Scherman D, Henry JP. Characteristics of the transport of quaternary ammonium 1-methyl-4-phenylpyridine by chromaffin granules. Biochem Pharmacol. 1988;37:4381–4387.
  PubMed CAS Google Scholar
• Del Zompo M, Piccardi MP, Ruiu S, Quartu M, Gessa GL, Vaccari A. Selective MMP+ uptake into synaptic dopamine vesicles: possible involvement in MPTP neurotoxicity. Br J Pharmacol. 1993;109:411–414.
  PubMed Google Scholar
• Moriyama Y, Amakatsu K, Futai M. Uptake of the neurotoxin, 4-methylphenylpyridinium, into chromaffin granules and synpatic vesicles: a proton gradient, drives its uptake through monoamine transporter. Arch Biochem Biophys. 1993:305:271–277.
  PubMed CAS Google Scholar
• Takahashi N, Miner LL, Sora I, et al. VMAT2 knockout mice: heterozygotes display reduced amphetamine-conditioned reward, enhanced amphetamine locomotion, and enhanced MPTP toxicity. Proc Natl Acad Sci USA. 1997;94:9938–9943.
  PubMed CAS Google Scholar
• Speciale SG, Liang CL, Sonsalla PK, Edwards RH, German DC, The neurotoxin 1-methyl-4-phenylpyridinium is sequestered within neurons that contain the vesicular monoamine transporter. Neuroscience. 1998;84:1177–1185.
  PubMed CAS Google Scholar
• Gainetdinov RR, Fumagalli F, Wang YM, et al.. Increased MPTP neurotoxicity in vesicular monoamine transporter 2 heterozygote knockout mice. J Neurochem. 1998;70:1973–1978.
  PubMed CAS Google Scholar
• German DC, Liang CL, Manaye KF, Lane K, Sonsalla PK. Pharmacological inactivation of the vesicular monoamine transporter can enhance 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced neurodegeneration of midbrain dopaminergic, neurons, but not locus coeruleus noradrenergic neurons. Neuroscience. 2000;101:1063–1069.
  PubMed CAS Google Scholar
• Staal RGW, Sonsalla PK. Inhibition of brain vesicular monoamine transporter (VMAT2) enhances 1-methyl-4-phenylpyridinium neurotoxicity in vivo in rat striata. J Pharmacol Exp Ther. 2000;293:336–342.
  PubMed CAS Google Scholar
• Mooslehner KA, Chan PM, Xu W, et al. Mice with very low expression of the vesicular monoamine transporter 2 gene survive into adulthood: potential mouse model for parkinsonism. Mol Cell Biol. 2001;21:5321–5331.
  PubMed CAS Google Scholar
• Fumagalli F, Gainetdinov RR, Wang, YM, Valenzano KJ, Miller GW, Caron MG. Increased methamphetamine neurotoxicity in heterozygous vesicular monoamine transporter 2 knock-out mice. J Neurosci. 1999;19:2424–2431.
  PubMed CAS Google Scholar
• Kariya S, Takahashi N, Hirano M, Ueno S. Increased vulnerability to L-DOPA toxicity in dopaminergic neurons from VMAT2 heterozygote knockout mice. J Mol Neurosci. 2005;27:277–280.
  PubMed CAS Google Scholar
• Glatt CE, Wahner AD, White DJ, Ruiz-Linares A, Ritz B, Gain-of-function haplotypes in the vesicular monoamine transporter prom oter are protective for Parkinson disease in women. Hum Mol Genet. 2005;15:299–305.
  PubMed Google Scholar
• Sandoval V, Riddle EL, Hanson GR, Fleckenstein AE. Methylphenidate alters vesicular monoamine transport and prevents methamphetamine-induced dopaminergic deficits. J Pharmacol Exp Ther. 2002:304:1181–1187.
  Google Scholar
• Hanson GR, Sandoval V, Riddle E, Fleckenstein AE. Psychostimulants and vesicle trafficking: a novel mechanism and therapeutic implications. Ann NY Acad Sci.. 2004;1025:146–150.
  PubMed CAS Google Scholar
• Hall ED, Andrus PK, Oostveen JA, Althaus JS, Von Voigtlander PF. Neuroprotective effects of the dopamine D2/D3 agonist pramipexole against postischemic or methamphetamine-induced degeneration of nigrostriatal neurons. Brain Res. 1996;742:80–88.
  PubMed CAS Google Scholar
• Sethy VH, Wu H, Oostveen JA, Hall ED. Neuroprotective effects of the dopamine agonist pramipexole and bromocriptine in 3-acetylpyridine-treated rats. Brain Res. 1997;754:181–186.
  PubMed CAS Google Scholar
• Truong JG, Rau KS, Hanson GR, Fleckenstein AE. Pramipexole increases vesicular dopamine uptake: implications for treatment of Parkinson's neurodegeneration. Eur J Pharmacol 2003;474:223–226.
  PubMed CAS Google Scholar
• Truong JG, Hanson GR, Fleckenstein AE. Apomorphine increases vesicular monoamine transporter-2 function: implications for neurodegeneration. Eur J Pharmacol. 2004;492:143–147.
  PubMed CAS Google Scholar
• Amara SG, Sonders MS. Neurotransmitter transporters as molecular targets for addictive drugs Drug Alcohol Depend. 1998;51:87–96.
  PubMed CAS Google Scholar
• Wise RA, Bozarth MA. A psychomotor stimulant theory of addiction. Psychol Rev. 1987;94:469–492.
  PubMed CAS Google Scholar
• Koob GF. Neural mechanisms of drug reinforcement. Ann N Y Acad Sci. 1992;654:171–191.
  PubMed CAS Google Scholar
• Fleckenstein AE, Hanson GR. Impact of psychostimulants on vesicular monoamine transporter function. Eur J Pharmacol. 2003;479:283–289.
  PubMed CAS Google Scholar
• Riddle EL, Fleckenstein AE, Hanson GR. Role of monoamine transporters in mediating psychostimulant effects. AAPS J. 2005;7:E847-E851 serial online.
  PubMed CAS Google Scholar
• Brown JM, Hanson GR, Fleckenstein AE. Regulation of the vesicular monoamine transporter-2: a novel mechanism for cocaine and other psychostimulants. J Pharmacol Exp Ther. 2001;296:762–767.
  PubMed CAS Google Scholar
• Sulzer D, Maidment NT, Rayport S. Amphetamine and other weak bases act to promote reverse transport of dopamine in ventral midbrain neurons. J Neurochem. 1993;60:527–535.
  PubMed CAS Google Scholar
• Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A. Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995;15:4102–4108.
  PubMed CAS Google Scholar
• Johnson RG. Accumulation of biological amines into chromaffin granules: a model for hormone and neurotransmitter transport. Physiol Rev. 1988;68:232–307.
  PubMed CAS Google Scholar
• Sulzer D, Rayport S. Amphetamine and other psychostimulants reduce pH gradients in midbrain dopaminergic neurons and chromaffin granules: a mechanism of action. Neuron. 1990;5:797–808.
  PubMed CAS Google Scholar
• Brown JM, Hanson GR, Fleckenstein AE. Methamphetamine rapidly decreases vesicular dopamine uptake. J Neurochem. 2000;74:2221–2223.
  PubMed CAS Google Scholar
• Wang Y, Gainetdinov RR, Fumagalli F, et al., Knockout of the vesicular monoamine transporter 2 gene results in neonatal death and supersensitivity to cocaine and amphetamine. Neuron. 1997;19:1285–1296.
  PubMed CAS Google Scholar
• Pletscher A, Brossi A, Gey KF. Benzoquinolizine derivatives: a new class of monoamine decreasing drugs with psychotropic action. Int Rev Neurobiol. 1962;4:275–306.
  Google Scholar
• Pettibone DJ, Pflueger AB, Totaro JA. Tetrabenazine-induced depletion of brain monoamines: mechanism by which desmethylimipramine protects cortical norepinephrine. Eur J Pharmacol. 1984;102:431–436.
  PubMed CAS Google Scholar
• Brossi A, Lindlar H, Walter M, Schnider O. Synthesis in the emetine series, I: 2-oxohydrobenzo[a]quinolizines. Helv Chim Acta. 1958;41:1793–1806.
  CAS Google Scholar
• Kenney C, Jankovic J. Tetrabenazine in the treatment of hyperkinetic movement disorders. Expert Rev Neurother. 2006;6:7–17.
  PubMed CAS Google Scholar
• Huntington Study Group. Tetrabenazine as antichorea therapy in Huntington disease. Neurology. 2006;66:366–372.
  Google Scholar
• Jankovic J, Beach J. Long-term effects of tetrabenazine in hyperkinetic movement disorders. Neurology. 1997;48:358–362.
  PubMed CAS Google Scholar
• Reches A, Burke RE, Kuhn CM, Hassan MN, Jackson VR, Fahn S. Tetrabenazine, an amine-depleting drug, also blocks dopamine receptors in rat brain. J Pharmacol Exp Ther. 1983;225:515–521.
  PubMed CAS Google Scholar
• DaSilva JN, Kilbourn MR, Mangner TJ. Synthesis of [11C]tetrabenazine a vesicular monoamine uptake inhibitor, for PET imaging studies. Appl Radiat Isot. 1993;44:673–676.
  PubMed CAS Google Scholar
• Kilbourn MR, DaSilva JN, Frey KA, Koeppe RA, Kuhl DE. In vivo imaging of vesicular monoamine transporters in human brain using [11C]tetrabenazine and positron emission tomography. J Neurochem. 1993;60:2315–2318.
  PubMed CAS Google Scholar
• DaSilva JN, Kilbourn MR, Domino EF. In vivo imaging of monoaminergic nerve terminals in normal and MPTP-lesioned primate brain using positron emission tomography (PET) and [11C]tetrabenazine. Synapse. 1993;14:128–131.
  PubMed CAS Google Scholar
• DaSilva JN, Carey JE, Sherman PS, Pisani TJ, Kilbourn MR. Characterization of [11C]tetrabenazine as an in vivo radioligand for the vesicular monoamine transporter. Nucl Med Biol. 1994;21:151–156.
  PubMed CAS Google Scholar
• Kilbourn MR. PET radioligands for vesicular neurotransmitter transporters. Med Chem Res. 1994;5:113–126.
  Google Scholar
• Schwartz DE, Bruderer H, Rieder J, Brossi A. Metabolic studies of tetrabenazine, a psychotropic drug in animals and man. Biochem Pharmacol. 1966;15:645–655.
  PubMed CAS Google Scholar
• Scherman D, Raisman R, Ploska A, Agid Y. [3H]Dihydrotetrabenazine, a new in vitro monoaminergic probe for human brain. J Neurochem. 1988;50:1131–1136.
  PubMed CAS Google Scholar
• Masuo Y, Pelaprat D, Scherman D, Rostene W. [3H]Dihydrotetrabenazine, a new marker for the visualization of dopaminergic denervation in the rat striatum. Neurosci Lett. 1990;114:45–50.
  PubMed CAS Google Scholar
• Zucker M, Weizman A, Rehavi M. Characterization of high-affinity [3H]TBZOH binding to the human platelet vesicular monoamine transporter. Life Sci. 2001;69:2311–2317.
  PubMed CAS Google Scholar
• Jewett DM, Kilbourn MR, Lee LC. A simple synthesis of[11C]dihydrotetrabenazine (DTBZ). Nucl Med Biol. 1997;24:197–199.
  PubMed CAS Google Scholar
• Koeppe RA, Frey KA, Kume A, Albin R, Kilbourn MR, Kuhl DE. Equilibrium versus compartmental analysis for assessment of the vesicular monoamine transporter using (+)-[11C]dihydrotetrabenazine (DTBZ) and positron emission tomography. J Cereb Blood Flow Metab. 1997;17:919–931.
  PubMed CAS Google Scholar
• DaSilva JN, Kilbourn MR, Mangner TJ. Synthesis of a [11C]methoxy derivative of alpha-dihydrotetrabenazine: a radioligand for studying the vesicular monoamine transporter. Appl Radiat Isot. 1993;44:1487–1489.
  PubMed CAS Google Scholar
• Kilbourn MR, Lee LC, Heeg MJ, Jewett DM. Absolute configuration of (+)-dihydrotetrabenazine, an active metabolite of tetrabenazine. Chirality. 1997;9:59–62.
  PubMed CAS Google Scholar
• Kilbourn MR, Lee L, Vander Borght T, Jewett D, Frey K. Binding of alpha-dihydrotetrabenazine to the vesicular monoamine transporter is stereospecific. Eur J Pharmacol. 1995;278:249–252.
  PubMed CAS Google Scholar
• Kilbourn MR, Lee LC, Jewett DM, Vander Borght TM, Koeppe RA, Frey KA. In vitro and in vivo binding of α-dihydrotetrabenazine to the vesicular monoamine transporters is stereospecific. J Cereb Blood Flow Metab. 1995;15:S650.
  Google Scholar
• Clarke I, Turtle R, Johnston G, inventors. Cambridge Laboratories Limited, UK, assignee. Preparation of dihydrotetrabenazines with affinity for monoamine transporters for use in pharmaceutical compositions for the treatment of hyperkinetic disorders. WO 2 005 077 946. February 11, 2005.
• Tridgett R, Clarke I, Turtle R, Johnston G, inventors. Cambridge Laboratories Limited, UK, assignee. Preparation of dihydrotetrabenazine isomers for the treatment of hyperkinetic movement disorders. GB 2 410 947. February 11, 2004.
• Vander Borght TM, Sima AAF, Kilbourn MR, Desmond TJ, Kuhl DE, Frey KA. [3H]Methoxytetrabenazine: a high specific activity ligand for estimating monoaminergic neuronal integrity. Neuroscience. 1995;68:955–962.
  Google Scholar
• Vander Borght TM, Kilbourn MR, Koeppe RA, et al. In vivo imaging of the brain vesicular monoamine transporter. J Nucl Med. 1995;36:2252–2260.
  Google Scholar
• Kilbourn MR, Sherman PS, Abbott LC. Mutant mouse strains as models for in vivo radiotracer evaluations: [11C]methoxytetrabenazine ([11C]MTBZ) in tottering mice. Nucl Med Biol. 1995;22:565–567.
  PubMed CAS Google Scholar
• F. Hoffmann-La Roche & Co inventor. F. Hoffmann-La Roche & Co, assignee. Substituted 2-hydroxy-1,2,3,4,6,7-hexahydrobenzo[a]quin olizines and their salts. GB 839 105. June 29, 1960.
• F. Hoffmann-La Roche & Co. inventor. F. Hoffmann-La Roche & Co, assignee. Benzo[a]quinolizine derivatives. BE 633 559. December 13, 1963.
• F. Hoffmann-La Roche & Co. inventor. F. Hoffmann-La Roche & Co, assignee. Substituted tetrahydrobenzo[a]quinolizines. BE 636 798. March 2, 1964.
• Lee LC, Vander Borght T, Sherman PS, Frey KA, Kilbourn MR. In vitro and in vivo studies of benzoisoquinoline ligands for the brain synaptic vesicle monoamine transporter. J Med Chem. 1996;39:191–196.
  PubMed CAS Google Scholar
• Canney DJ, Guo YZ, Kung MP, Kung HF. Synthesis and preliminary evaluation of an iodovinyl-tetrabenazine analog as a marker for the vesicular monoamine transporter. J Labelled Compd Radiopharm. 1993;33:355–368.
  CAS Google Scholar
• Kung MP, Canney DJ, Frederick D, Zhuang Z, Billings JJ, Kung HF. Binding of 125I-iodovinyltetrabenazine to CNS vesicular monoamine transport sites. Synapse. 1994;18:225–232.
  PubMed CAS Google Scholar
• Clarke FH, Hill RT, Koo J, et al.. A series of hexahydro[1,4]oxazino [3,4-a]isoquinolines as potential neuroleptics. J Med Chem. 1978;21:785–791.
  PubMed CAS Google Scholar
• Fahrenholtz KE, Capomaggi A, Lurie M, Goldberg MW, Kierstead RW. Octahydrophenanthrene analogs of tetrabenazine. J Med Chem. 1966;9:304–310.
  PubMed CAS Google Scholar
• Saner A, Pletscher A. A benzo[a]quinolizine derivative with a neuroleptic-like action on cerebral monoamine turnover. J Pharmacol Exp Ther. 1977;203:556–563.
  PubMed CAS Google Scholar
• Harnden MR, Short JH. 2-Thio-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizines. J Med Chem. 1967;10:1183–1184.
  PubMed CAS Google Scholar
• Aranda G, Beaucourt JP, Ponchant M, Isambert MF, Henry JP. Synthesis and biological activity of iodinated and photosensitive derivatives of tetrabenazine. Eur J Med Chem 1990;25:369–374.
  CAS Google Scholar
• Scherman D, Gasnier B, Jaudon P, Henry JP. Hydrophobicity of the tetrabenazine-binding site of the chromaffin granule monoamine transporter. Mol Pharmacol. 1988;33:72–77.
  PubMed CAS Google Scholar
• Canney DJ, Kung MP, Kung HF. Amino- and amidotetrabenazine derivatives: synthesis and evaluation as potential ligands for the vesicular monoamine transporter. Nucl Med Biol. 1995;22:527–535.
  PubMed CAS Google Scholar
• Leysen JE, Niemegeers CJE, Van Nueten JM, Laduron PM. [3H]Ketanserin (R-4-1468), a selective 3H-ligand for serotonin2 receptor binding sites. Binding properties, brain distribution, and functional role. Mol Pharmacol. 1982;21:301–314.
  PubMed CAS Google Scholar
• Darchen F, Scherman D, Laduron PM, Henry JP. Ketanserin binds to the monoamine transporter of chromaffin granules and of synaptic vesicles. Mol Pharmacol. 1988;33:672–677.
  PubMed CAS Google Scholar
• Henry JP, Gasnier B, Isambert MF, Darchen F, Scherman D. Ketanserin as a ligand of the vesicular monoamine transporter. Adv Biosci. 1991;82:147–150.
  CAS Google Scholar
• Leysen JE, Eens A, Gommeren W, Van Gompel P, Wynants J, Janssen PAJ. Identification of nonserotonergic [3H]ketanserin binding sites associated with nerve terminals in rat brain and with platelets; relation with release of biogenic amine metabolites induced by ketanserin-and tetrabenazine-like drugs. J Pharmacol Exp Ther. 1988;244:310–321.
  PubMed CAS Google Scholar
• Isambert MF, Gasnier B, Laduron PM, Henry JP. Photoaffinity labeling of the monoamine transporter of bovine chromaffin granules and other monoamine storage vesicles using 7-azido-8-[125I]iodoketanserin. Biochemistry. 1989;28:2265–2270.
  PubMed CAS Google Scholar
• Yamada S, Isogai M, Kagawa Y, et al. Brain nicotinic acetylcholine receptors: biochemical characterization by neosurugatoxin. Mol Pharmacol. 1985;28:120–127.
  PubMed CAS Google Scholar
• Lippiello PM, Fernandes KG. The binding of L-[3H]nicotine to a single class of high affinity sites in rat brain membranes. Mol Pharmacol. 1986;29:448–454.
  PubMed CAS Google Scholar
• Banerjee S, Abood LG. Nicotine antagonists: phosphoinositide turnover and receptor binding to determine muscarinic properties. Biochem Pharmacol. 1989;38:2933–2935.
  CAS Google Scholar
• Broussolle EP, Wong DF, Fanelli RJ, London ED. In vivo specific binding of [3H]L-nicotine in the mouse brain. Life Sci. 1989;44:1123–1132.
  PubMed CAS Google Scholar
• Damaj MI, Patrick GS, Creasy KR, Martin BR. Pharmacology of lobeline, a nicotinic receptor ligand. J Pharmacol Exp Ther. 1997;282:410–419.
  PubMed CAS Google Scholar
• Barlow RB, Johnson O. Relations between structure and nicotine-like activity: X-ray crystal structure analysis of (−)-cytisine and (−)-lobeline hydrochloride and a comparison with (−)-nicotine and other nicotine-like compounds. Br J Pharmacol. 1989;98:799–808.
  PubMed CAS Google Scholar
• Olin BR, Hebel SK, Gremp JL, Hulbertt MK. Smoking deterrents. In: Olin BR, Hebel SK, Gremp JL, Hulbertt MK, eds. Drug Facts and Comparisons. St. Louis, MO: JB Lippincott; 1995:3087–3095
  Google Scholar
• Sloan JW, Martin WR, Bostwick M, Hook R, Wala E. The competitive binding characteristics of nicotine ligands and their pharmacology. Pharmacol Biochem Behav. 1988;30:255–267.
  PubMed CAS Google Scholar
• Brioni JD, O'Neill AB, Kim DJB, Decker MW. Nicotine receptor agonists exhibit anxiolytic-like effects on the elevated plus-maze test. Eur J Pharmacol. 1993;238:1–8.
  PubMed CAS Google Scholar
• Decker MW, Majchzark MJ, Arneric SP. Effects of lobeline, a nicotine receptor agonist, on learning and memory. Pharmacol Biochem Behav. 1993;45:571–576.
  PubMed CAS Google Scholar
• Rasmussen T, Swedberg MDB. Reinforcing effects of nicotinic compounds: intravenous self-administration in drug-naive mice. Pharmacol Biochem Behav. 1998;60:567–573.
  PubMed CAS Google Scholar
• Harrod SB, Dwoskin LP, Green TA, Gehrke BJ, Bardo MT. Lobeline does not serve as a reinforcer in rats. Psychopharmacology (Berl). 2003;165:397–404.
  CAS Google Scholar
• Fudala PJ, Iwamoto ET. Further studies on nicotine-induced conditioned place preference in the rat. Pharmacol Biochem Behav. 1986;25:1041–1049.
  PubMed CAS Google Scholar
• Stolerman IP, Garcha HS, Mirza NR. Dissociation between the locomotor stimulant and depressant effects of nicotinic agonists in rats. Psychopharmacology (Berl). 1995;117:430–437.
  CAS Google Scholar
• Dwoskin LP, Crooks PA. A novel mechanism of action and potential use for lobeline as a treatment for psychostimulant abuse. Biochem Pharmacol. 2002;63:89–98.
  PubMed CAS Google Scholar
• Gallardo KA, Leslie FM. Nicotine-stimulated release of [3H]norepinephrine from fetal, rat locus coeruleus cells in culture. J Neurochem. 1998;70:663–670.
  PubMed CAS Google Scholar
• Miller DK, Crooks PA, Dwoskin LP. Lobeline inhibits nicotine-evoked [3H]dopamine overflow from rat striatal slices and nicotine-evoked 86Rb+ efflux from thalamic synaptosomes. Neuropharmacology. 2000;39:2654–2662.
  PubMed CAS Google Scholar
• Miller DK, Crooks PA, Zheng G, Grinevich VP, Norrholm S, Dwoskin LP. Lobeline analogues with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters. J Pharmacol Exp Ther. 2004;310:1035–1045.
  PubMed CAS Google Scholar
• Briggs CA, McKenna DG. Activation and inhibition of the human alpha 7 nicotinic acetylcholine receptor by agonist binding affinity. Mol Pharmacol. 1998;37:1095–1102.
  CAS Google Scholar
• Teng L, Crooks PA, Sonsalla PK, Dwoskin LP. Lobeline and nicotine evoke [3H]overflow from rat striatal slices preloaded with [3H]dopamine: differential inhibition of synaptosomal and vesicular [3H]dopamine uptake. J Pharmacol Exp Ther. 1997;280:1432–1444.
  PubMed CAS Google Scholar
• Teng L, Crooks PA, Dwoskin LP. Lobeline displaces [3H]dihydrotetrabenazine binding and releases [3H]dopamine from rat striatal synaptic vesicles: comparison with d-amphetamine. J Neurochem. 1998;71:258–265.
  Article PubMed CAS Google Scholar
• Miller DK, Crooks PA, Teng L, et al. Lobeline inhibits the neurochemical and behavioral effects of amphetamine. J. Pharmacol Exp Ther. 2001;296:1023–1034.
  PubMed CAS Google Scholar
• Miller DK, Harrod SB, Green TA, Wong MY, Bardo MT, Dwoskin LP. Lobeline attenuates the locomotor stimulation induced by repeated nicotine administration in rats. Pharmacol Biochem Behav. 2003;74:279–286.
  PubMed CAS Google Scholar
• Harrod SB, Dwoskin LP, Crooks PA, Klebaur JE, Bardo MT. Lobeline attenuates d-methamphetamine self-administration in rats. J Pharmacol Exp Ther. 2001;298:172–179.
  PubMed CAS Google Scholar
• Zheng G, Dwoskin LP, Deaciuc AG, Norrholm SD, Crooks PA. Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter. J Med Chem. 2005;48:5551–5560.
  PubMed CAS Google Scholar
• Zheng G, Dwoskin LP, Deaciuc AG, Zhu J, Jones MD, Crooks PA. Lobelane analogues, as novel ligands for the vesicular monoamine transporter-2. Bioorg Med Chem. 2005;13:3899–3909.
  Article PubMed CAS Google Scholar
• Zheng G, Dwoskin LP, Deaciuc AG, Crooks PA. Synthesis and evaluation of a series of tropane analogues as novel vesicular monoamine transporter-2 ligands. Bioorg Med Chem Lett. 2005;15:4463–4466.
  PubMed CAS Google Scholar
• Perera RP, Wimalasena DS, Wimalasena K. Characterization of a series of 3-amino-2-phenyl-propene derivatives as novel bovine chromaffin vesicular monoamine transporter inhibitors. J Med Chem. 2003;46:2599–2605.
  PubMed CAS Google Scholar
• Merickel A, Rosandich P, Peter D, Edwards, RH. Identification of residues involved in substrate recognition by a vesicular monoamine transporter. J Biol Chem. 1995;270:25798–25804.
  PubMed CAS Google Scholar
• Merickel A, Kaback HR, Edwards RH. Charged residues in transmembrane domains II and XI of a vesicular monoamine transporter form a charge pair that promotes high affinity substrate recognition. J Biol Chem. 1997;272:5403–5408.
  PubMed CAS Google Scholar
• Peter D, Vu T, Edwards RH. Chimeric vesicular monoamine transporters identify structural domains that influence substrate affinity and sensitivity to tetrabenazine. J Biol Chem. 1996;271:2979–2986.
  PubMed CAS Google Scholar
• Finn JP, III, Edwards RH. Individual residues contribute to multiple differences in ligand recognition between vesicular monoamine transporters 1 and 2. J Biol Chem. 1997;272:16301–16307.
  PubMed CAS Google Scholar
• Sievert MK, Ruoho AE. Peptide mapping of the [125I]iodoazidok etanserin and [125I]2-N-[(3′-iodo-4′-azidophenyl)propionyl]tetrabenazine binding sites for the synaptic vesicle monoamine transporter. J Biol Chem. 1997;272:26049–26055.
  PubMed CAS Google Scholar
• Thiriot DS, Ruoho AE. Mutagenesis and derivatization of human vesicle monoamine transporter 2 (VMAT2) cysteines identifies transporter domains involved in tetrabenazine binding and substrate transport. J Biol Chem. 2001;276:27304–27315.
  PubMed CAS Google Scholar
• Thiriot DS, Sievert MK, Ruoho AE. Identification of human vesicle monoamine transporter (VMAT2) lumenal cysteines that form an intramolecular disulfide bond. Biochemistry. 2002;41: 6346–6353.
  PubMed CAS Google Scholar