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Volumn 11, Issue 9, 2011, Pages 1103-1127

Design, synthesis and interaction at the vesicular monoamine transporter-2 of lobeline analogs: Potential pharmacotherapies for the treatment of psychostimulant abuse

Author keywords

Computational modeling; Lobeline; Lobeline analogs; Psychostimulant abuse; Vesicular monoamine transporter 2 (VMAT2)

Indexed keywords

ETHYLENE; HYDROXYL GROUP; KETONE; LIGAND; LOBELINE; METHYL GROUP; PIPERIDINE; PYRROLIDINE DERIVATIVE; TROPANE DERIVATIVE; VESICULAR MONOAMINE TRANSPORTER 2;

EID: 79954513618     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802611795371332     Document Type: Article
Times cited : (14)

References (108)
  • 1
    • 0029896966 scopus 로고    scopus 로고
    • Distinct pharmacological properties and distribution in neurons and endocrine cells of isoforms of the human vesicular monoamine transporter
    • Erickson, J. D.; Schafer, M. K.; Bonner, T. I.; Eiden, L. E.; Weihe E. Distinct pharmacological properties and distribution in neurons and endocrine cells of isoforms of the human vesicular monoamine transporter. Proc. Natl. Acad. Sci., 1996, 93, 5166-5171.
    • (1996) Proc. Natl. Acad. Sci. , vol.93 , pp. 5166-5171
    • Erickson, J.D.1    Schafer, M.K.2    Bonner, T.I.3    Eiden, L.E.4    Weihe, E.5
  • 2
    • 0027424072 scopus 로고
    • Functional identification and molecular cloning of a human brain vesicle monoamine transporter
    • Erickson, J. D.; Eiden, L. Functional identification and molecular cloning of a human brain vesicle monoamine transporter. J. Neurochem., 1993, 61, 2314-2317.
    • (1993) J. Neurochem. , vol.61 , pp. 2314-2317
    • Erickson, J.D.1    Eiden, L.2
  • 3
    • 0026458380 scopus 로고
    • Expression cloning of a reserpine-sensitive vesicular monoamine transporter
    • Erickson, J. D.; Eiden, L. E; Hoffman, B. J. Expression cloning of a reserpine-sensitive vesicular monoamine transporter. Proc. Natl. Acad. Sci., 1992, 89, 10993-10997.
    • (1992) Proc. Natl. Acad. Sci. , vol.89 , pp. 10993-10997
    • Erickson, J.D.1    Eiden, L.E.2    Hoffman, B.J.3
  • 4
    • 33751242500 scopus 로고    scopus 로고
    • Vesicular monoamine transporter-2: Role as a novel target for drug development
    • Zheng, G.; Dwoskin, L. P.; Crooks, P. A. Vesicular monoamine transporter-2: Role as a novel target for drug development. AAPS J., 2006, 4(8), E682-E692.
    • (2006) AAPS J. , vol.4 , Issue.8
    • Zheng, G.1    Dwoskin, L.P.2    Crooks, P.A.3
  • 5
    • 0028263975 scopus 로고
    • The chromaffin granule and synaptic vesicle amine transporters differ in substrate recognition and sensitivity to inhibitors
    • Peter, D.; Jimenez, J.; Liu, Y.; Kim, J.; Edwards, R. H. The chromaffin granule and synaptic vesicle amine transporters differ in substrate recognition and sensitivity to inhibitors. J. Biol. Chem., 1994, 269, 7231-7237.
    • (1994) J. Biol. Chem. , vol.269 , pp. 7231-7237
    • Peter, D.1    Jimenez, J.2    Liu, Y.3    Kim, J.4    Edwards, R.H.5
  • 7
    • 0028508560 scopus 로고
    • Localization of vesicular monoamine transporter isoforms (VMAT1 and VMAT2) to endocrine cells and neurons in rat
    • Weihe, E., Schafer M. K.; Erickson J. D.; Eiden L. E. al. Localization of vesicular monoamine transporter isoforms (VMAT1 and VMAT2) to endocrine cells and neurons in rat. J. Mol. Neurosci., 1994, 5, 149-164.
    • (1994) J. Mol. Neurosci. , vol.5 , pp. 149-164
    • Weihe E.Schafer, M.K.1    Erickson, J.D.2    Eiden, L.E.3
  • 10
    • 0027955777 scopus 로고
    • Schuldiner, SCloning and functional expression of a tetrabenazine sensitive vesicular monoamine transporter from bovine chromaffin granules
    • Howell, M.; Shirvan, A.; Stern-Bach, Y.; Steiner-Mordoch, S.; Strasser, J.E.; Dean, G.E.; Schuldiner, SCloning and functional expression of a tetrabenazine sensitive vesicular monoamine transporter from bovine chromaffin granules. FEBS Lett., 1994, 338, 16-22.
    • (1994) FEBS Lett. , vol.338 , pp. 16-22
    • Howell, M.1    Shirvan, A.2    Stern-Bach, Y.3    Steiner-Mordoch, S.4    Strasser, J.E.5    Dean, G.E.6
  • 12
    • 0032505028 scopus 로고    scopus 로고
    • Ontogeny of vesicular monoamine transporter mRNAs VMAT1 and VMAT2, II. Expression in neural crest derivatives and their target sites in the rat
    • Hansson, S. R.; Mezey, E; Hoffman, B. J. Ontogeny of vesicular monoamine transporter mRNAs VMAT1 and VMAT2, II. Expression in neural crest derivatives and their target sites in the rat. Dev. Brain Res., 1998, 110, 159-174.
    • (1998) Dev. Brain Res. , vol.110 , pp. 159-174
    • Hansson, S.R.1    Mezey, E.2    Hoffman, B.J.3
  • 13
    • 0017344836 scopus 로고
    • Effect of neuroleptics and other drugs on monoamine uptake by membranes of adrenal chromaffin granules
    • Pletscher, A. Effect of neuroleptics and other drugs on monoamine uptake by membranes of adrenal chromaffin granules. Br. J. Pharmacol., 1977, 59, 419-424.
    • (1977) Br. J. Pharmacol. , vol.59 , pp. 419-424
    • Pletscher, A.1
  • 14
    • 0021288772 scopus 로고
    • Reserpine binding to bovine chromaffin granule membranes
    • Darchen, F.; Scherman, D; Henry, J. P. Reserpine binding to bovine chromaffin granule membranes. Mol. Pharmacol., 1984, 25, 113-122.
    • (1984) Mol. Pharmacol. , vol.25 , pp. 113-122
    • Darchen, F.1    Scherman, D.2    Henry, J.P.3
  • 15
    • 0024402663 scopus 로고
    • Radioligands of the vesicular monoamine transporter and their use as markers of monoamine storage vesicles
    • Scherman, D.; Henry, J. P. Radioligands of the vesicular monoamine transporter and their use as markers of monoamine storage vesicles. Biochem. Pharmacol., 1989, 38, 2395-2404.
    • (1989) Biochem. Pharmacol. , vol.38 , pp. 2395-2404
    • Scherman, D.1    Henry, J.P.2
  • 16
    • 0024402663 scopus 로고
    • Radioligands of the vesicular monoamine transporter and their use as markers of monoamine storage vesicles
    • Henry, J. P.; Scherman, D. Radioligands of the vesicular monoamine transporter and their use as markers of monoamine storage vesicles. Biochem. Pharmacol., 1989, 38, 2395-2404.
    • (1989) Biochem. Pharmacol. , vol.38 , pp. 2395-2404
    • Henry, J.P.1    Scherman, D.2
  • 18
    • 0032104581 scopus 로고    scopus 로고
    • Neurotransmitter transporters as molecular targets for addictive drugs
    • Amara, S. G.; Sonders, M. S. Neurotransmitter transporters as molecular targets for addictive drugs. Drug Alcohol Depend., 1998, 51, 87-96.
    • (1998) Drug Alcohol Depend. , vol.51 , pp. 87-96
    • Amara, S.G.1    Sonders, M.S.2
  • 19
    • 0023426876 scopus 로고
    • A psychostimulant theory of addiction
    • Wise, R. A.; Bozarth, M. A. A psychostimulant theory of addiction. Psychol. Rev., 1987, 94, 469-492.
    • (1987) Psychol. Rev. , vol.94 , pp. 469-492
    • Wise, R.A.1    Bozarth, M.A.2
  • 20
    • 0026759536 scopus 로고
    • Neural mechanisms of drug reinforcement
    • Koob, G. F. Neural mechanisms of drug reinforcement. Ann. N Y Acad. Sci., 1992, 654, 171-191.
    • (1992) Ann. N Y Acad. Sci. , vol.654 , pp. 171-191
    • Koob, G.F.1
  • 21
    • 0242721911 scopus 로고    scopus 로고
    • Impact of psychostimulants on vesicular monoamine transporter function
    • Fleckenstein, A. E.; Hanson, G. R. Impact of psychostimulants on vesicular monoamine transporter function. Eur. J. Pharmacol., 2003, 479, 283-289.
    • (2003) Eur. J. Pharmacol. , vol.479 , pp. 283-289
    • Fleckenstein, A.E.1    Hanson, G.R.2
  • 22
    • 33646637279 scopus 로고    scopus 로고
    • Role of monoamine transporters in mediating psychostimulant effects
    • Riddle, E. L.; Fleckenstein, A. E.; Hanson, G. R. Role of monoamine transporters in mediating psychostimulant effects. AAPS J., 2005, 7, E847-E851.
    • (2005) AAPS J. , vol.7
    • Riddle, E.L.1    Fleckenstein, A.E.2    Hanson, G.R.3
  • 23
    • 0035122979 scopus 로고    scopus 로고
    • Regulation of the vesicular monoamine transporter-2: A novel mechanism for cocaine and other psychostimulants
    • Brown, J. M.; Hanson, G. R.; Fleckenstein, A. E. Regulation of the vesicular monoamine transporter-2: A novel mechanism for cocaine and other psychostimulants. J. Pharmacol. Exp. Ther., 2001, 296, 762-767.
    • (2001) J. Pharmacol. Exp. Ther. , vol.296 , pp. 762-767
    • Brown, J.M.1    Hanson, G.R.2    Fleckenstein, A.E.3
  • 24
    • 0027395913 scopus 로고
    • Amphetamine and other weak bases act to promote reverse transport of dopamine in ventral midbrain neurons
    • Sulzer, D.; Maidment, N. T.; Rayport, S. Amphetamine and other weak bases act to promote reverse transport of dopamine in ventral midbrain neurons. J. Neurochem., 1993, 60, 527-535.
    • (1993) J. Neurochem. , vol.60 , pp. 527-535
    • Sulzer, D.1    Maidment, N.T.2    Rayport, S.3
  • 25
    • 0029032794 scopus 로고
    • Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport
    • Sulzer, D.; Chem, T. K.; Lau, Y. Y.; 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.
    • (1995) J. Neurosci. , vol.15 , pp. 4102-4108
    • Sulzer, D.1    Chem, T.K.2    Lau, Y.Y.3    Kristensen, H.4    Rayport, S.5    Ewing, A.6
  • 26
    • 0023872141 scopus 로고
    • Accumulation of biological amines into chromaffin granules: A model for hormone and neurotransmitter transport
    • Johnson, R. G. Accumulation of biological amines into chromaffin granules: A model for hormone and neurotransmitter transport. Physiol. Rev., 1988, 68, 232-307.
    • (1988) Physiol. Rev. , vol.68 , pp. 232-307
    • Johnson, R.G.1
  • 27
    • 0025647857 scopus 로고
    • Amphetamine and other psychostimulants reduce pH gradients in midbrain dopaminergic neurons and chromaffin granules: A mechanism of action
    • 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.
    • (1990) Neuron. , vol.5 , pp. 797-808
    • Sulzer, D.1    Rayport, S.2
  • 29
    • 0031458923 scopus 로고    scopus 로고
    • Knockout of the vesicular monoamine transporter 2 gene results in neonatal death and supersensitivity to cocaine and amphetamine
    • Wang, Y.; Gainetdinov, R. R.; Fumagalli, F.; Xu, F.; Jones, S. R.; Bock, C. B.; Miller, G. W.; Wightman, R. M.; Caron, M. G. Knockout of the vesicular monoamine transporter 2 gene results in neonatal death and supersensitivity to cocaine and amphetamine. Neuron, 1997, 19, 1285-1296.
    • (1997) Neuron , vol.19 , pp. 1285-1296
    • Wang, Y.1    Gainetdinov, R.R.2    Fumagalli, F.3    Xu, F.4    Jones, S.R.5    Bock, C.B.6    Miller, G.W.7    Wightman, R.M.8    Caron, M.G.9
  • 30
    • 0037081792 scopus 로고    scopus 로고
    • A Novel mechanism of action and potential use for lobeline as a treatment for psychostimulant abuse
    • Dwoskin, L. P.; Crooks, P. A. A Novel mechanism of action and potential use for lobeline as a treatment for psychostimulant abuse. Biochem. Pharmacol., 2002, 63, 89-98.
    • (2002) Biochem. Pharmacol. , vol.63 , pp. 89-98
    • Dwoskin, L.P.1    Crooks, P.A.2
  • 31
    • 0030038198 scopus 로고    scopus 로고
    • Chimeric vesicular monoamine transporters identify structural domains that influence substrate affinity and sensitivity to tetrabenazine
    • Peter, D.; Vu, T.; Edwards, R. H. Chimeric vesicular monoamine transporters identify structural domains that influence substrate affinity and sensitivity to tetrabenazine. J. Biol. Chem., 1996, 271, 2979-2986.
    • (1996) J. Biol. Chem. , vol.271 , pp. 2979-2986
    • Peter, D.1    Vu, T.2    Edwards, R.H.3
  • 33
    • 0028845359 scopus 로고
    • Identification of residues involved in substrate recognition by a vesicular monoamine transporter
    • Merickel, A.; Rosandich, P.; Peter, D.; Edwards, R. H. Identification of residues involved in substrate recognition by a vesicular monoamine transporter. J. Biol. Chem., 1995, 270, 25798-25804.
    • (1995) J. Biol. Chem. , vol.270 , pp. 25798-25804
    • Merickel, A.1    Rosandich, P.2    Peter, D.3    Edwards, R.H.4
  • 34
    • 0031054527 scopus 로고    scopus 로고
    • Charged residues in transmembrane domains II and XI of a vesicular monoamine transporter form a chard pair that promotes high affinity substrate recognition
    • Merickel, A.; Kaback, H. R.; Edwards, R. H. Charged residues in transmembrane domains II and XI of a vesicular monoamine transporter form a chard pair that promotes high affinity substrate recognition. J. Biol. Chem., 1997, 272, 5403-5408.
    • (1997) J. Biol. Chem. , vol.272 , pp. 5403-5408
    • Merickel, A.1    Kaback, H.R.2    Edwards, R.H.3
  • 35
    • 0030611051 scopus 로고    scopus 로고
    • 125I]2-N-[(3'-iodo-4'-azidophenyl) propionyl]tetrabenazine binding sites for the synaptic vesicle monoamine transporter
    • 125I]2-N-[(3'-iodo-4'-azidophenyl) propionyl]tetrabenazine binding sites for the synaptic vesicle monoamine transporter. J. Biol. Chem., 1997, 272, 26049-26055.
    • (1997) J. Biol. Chem. , vol.272 , pp. 26049-26055
    • Sievert, M.K.1    Ruoho, A.E.2
  • 36
    • 0035920208 scopus 로고    scopus 로고
    • Mutagenesis and deriviatization of human vesicle monoamine transporter 2 (VMAT2) cysteines identifies transporter domains involved in tetrabenazine binding and substrate transport
    • Thiriot, D. S.; Ruoho, A. E. Mutagenesis and deriviatization 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.
    • (2001) J. Biol. Chem. , vol.276 , pp. 27304-27315
    • Thiriot, D.S.1    Ruoho, A.E.2
  • 37
    • 3042665547 scopus 로고    scopus 로고
    • Structural conservation in the major facilitator superfamily as revealed by comparative modeling
    • Vardy, E.; Arkin, I. T.; Gottschalk, K. E.; Kaback, H. R.; Schuldiner, S. Structural conservation in the major facilitator superfamily as revealed by comparative modeling. Protein Sci., 2004, 13, 1982-1840.
    • (2004) Protein Sci. , vol.13 , pp. 1982-1840
    • Vardy, E.1    Arkin, I.T.2    Gottschalk, K.E.3    Kaback, H.R.4    Schuldiner, S.5
  • 38
    • 77951171061 scopus 로고    scopus 로고
    • Directed evolution reveals hidden properties of VMAT, a neurotransmitter transporter
    • Gros, Y.; Schuldiner, S. Directed evolution reveals hidden properties of VMAT, a neurotransmitter transporter. J. Biol. Chem., 2010, 285, 5076-5084.
    • (2010) J. Biol. Chem. , vol.285 , pp. 5076-5084
    • Gros, Y.1    Schuldiner, S.2
  • 40
    • 4644296823 scopus 로고    scopus 로고
    • History, chemistry and biology of alkaloids from Lobelia inflata
    • Felpin, F. X.; Lebreton, J. History, chemistry and biology of alkaloids from Lobelia inflata. Tetrahedron, 2004, 60, 10127-10153.
    • (2004) Tetrahedron , vol.60 , pp. 10127-10153
    • Felpin, F.X.1    Lebreton, J.2
  • 41
    • 2042546624 scopus 로고
    • Alkaloids of the Lobelia plant. I. (Preliminary Communication.)
    • Wieland, H. Alkaloids of the Lobelia plant. I. (Preliminary Communication.). Ber. Dtsch. Chem. Ges., 1921, 54B, 1784-1788.
    • (1921) Ber. Dtsch. Chem. Ges. , vol.54 B , pp. 1784-1788
    • Wieland, H.1
  • 43
    • 84978566068 scopus 로고
    • Lobelia alkaloids. Iii. Constitution of the Lobelia alkaloids
    • Wieland, H.; Dragendorff, O. Lobelia alkaloids. Iii. Constitution of the Lobelia alkaloids. Liebigs Ann. Chem., 1929, 473, 83-101.
    • (1929) Liebigs Ann. Chem. , vol.473 , pp. 83-101
    • Wieland, H.1    Dragendorff, O.2
  • 44
    • 84882395728 scopus 로고
    • Lobelia Alkaloids. Iv. Synthesis of Lobelia alkaloids
    • Wieland, H.; Drishaus, I. Lobelia Alkaloids. Iv. Synthesis of Lobelia alkaloids. Liebigs Ann. Chem., 1929, 473, 102-118.
    • (1929) Liebigs Ann. Chem. , vol.473 , pp. 102-118
    • Wieland, H.1    Drishaus, I.2
  • 45
    • 34548190264 scopus 로고
    • Lobelia alkaloids. V. Several bases accompanying lobeline and the reciprocal relations of the Lobelia alkaloids
    • Wieland, H.; Koschara, W.; Dane, E. Lobelia alkaloids. V. Several bases accompanying lobeline and the reciprocal relations of the Lobelia alkaloids. Liebigs Ann. Chem., 1929, 473, 118-126.
    • (1929) Liebigs Ann. Chem. , vol.473 , pp. 118-126
    • Wieland, H.1    Koschara, W.2    Dane, E.3
  • 47
    • 84978549411 scopus 로고
    • Syntheses and transformations of natural products under physiological conditions (model experiments on the question of the biogenesis of natural products). Iv. Syntheses of tropinone, pseudopelletierine, lobelanine and related qlkaloids under physiological conditions
    • Schopf, C.; Lehmann, G. Syntheses and transformations of natural products under physiological conditions (model experiments on the question of the biogenesis of natural products). Iv. Syntheses of tropinone, pseudopelletierine, lobelanine and related qlkaloids under physiological conditions. Liebigs Ann. Chem., 1935, 518, 1-37.
    • (1935) Liebigs Ann. Chem. , vol.518 , pp. 1-37
    • Schopf, C.1    Lehmann, G.2
  • 48
    • 84944192557 scopus 로고
    • Absolute configuration of (-)-lobeline and of its reduction products
    • Schoepf, C.; Mueller, E. Absolute configuration of (-)-lobeline and of its reduction products. Liebigs Ann. Chem., 1965, 687, 241-250.
    • (1965) Liebigs Ann. Chem. , vol.687 , pp. 241-250
    • Schoepf, C.1    Mueller, E.2
  • 49
    • 0242705214 scopus 로고    scopus 로고
    • Enantioselective access to Lobelia alkaloids
    • Compere, D.; Marazano, C.; Das, B. C. Enantioselective access to Lobelia alkaloids. J. Org. Chem., 1999, 64, 4528-4532.
    • (1999) J. Org. Chem. , vol.64 , pp. 4528-4532
    • Compere, D.1    Marazano, C.2    Das, B.C.3
  • 50
    • 0037184884 scopus 로고    scopus 로고
    • A highly stereoselective asymmetric synthesis of (-)-lobeline and (-)-sedamine
    • Felpin, F.-X.; Lebreton, J. A highly stereoselective asymmetric synthesis of (-)-lobeline and (-)-sedamine. J. Org. Chem., 2002, 67, 9192-9199.
    • (2002) J. Org. Chem. , vol.67 , pp. 9192-9199
    • Felpin, F.-X.1    Lebreton, J.2
  • 52
    • 34548153030 scopus 로고    scopus 로고
    • Enantioselective synthesis of lobeline via nonenzymatic desymmetrization
    • Birman, V. B.; Jiang, H.; Li, X. Enantioselective synthesis of lobeline via nonenzymatic desymmetrization. Org. Lett., 2007, 9, 3237-3240.
    • (2007) Org. Lett. , vol.9 , pp. 3237-3240
    • Birman, V.B.1    Jiang, H.2    Li, X.3
  • 53
    • 9344254954 scopus 로고    scopus 로고
    • Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: Application to the synthesis of (-)-sedamine
    • Zheng, G.; Dwoskin, L. P.; Crooks, P. A. Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: Application to the synthesis of (-)-sedamine. J. Org. Chem., 2004, 69, 8514-8517.
    • (2004) J. Org. Chem. , vol.69 , pp. 8514-8517
    • Zheng, G.1    Dwoskin, L.P.2    Crooks, P.A.3
  • 54
    • 0035931033 scopus 로고    scopus 로고
    • Unexpected retro-Michael reaction of (-)-(1's,4as,8ar)-and (+)-(1's,4ar,8as)-4a-ethyl-1-(1-phenylethyl)octahydroquinolin-7-ones
    • Vazquez, E.; Galindo, A.; Gnecco, D.; Bernes, S.; Teran, J. L.; Enriquez, R. G. Unexpected retro-Michael reaction of (-)-(1's,4as,8ar)-and (+)-(1's,4ar,8as)-4a-ethyl-1-(1-phenylethyl)octahydroquinolin-7-ones. Tetrahedron: Asymm., 2001, 12, 3209-3211.
    • (2001) Tetrahedron: Asymm. , vol.12 , pp. 3209-3211
    • Vazquez, E.1    Galindo, A.2    Gnecco, D.3    Bernes, S.4    Teran, J.L.5    Enriquez, R.G.6
  • 55
    • 22144454646 scopus 로고    scopus 로고
    • Asymmetric synthesis of 2,4,5-trisubstituted piperidines from sulfiniminederived D-amino B-ketoesters. formal synthesis of pseudodistomin B triacetate
    • Davis, F. A.; Zhang, J.; Li, Y.; Xu, H.; DeBrosse, C. Asymmetric synthesis of 2,4,5-trisubstituted piperidines from sulfiniminederived D-amino B-ketoesters. formal synthesis of pseudodistomin B triacetate. J. Org. Chem., 2005, 70, 5413-5419.
    • (2005) J. Org. Chem. , vol.70 , pp. 5413-5419
    • Davis, F.A.1    Zhang, J.2    Li, Y.3    Xu, H.4    DeBrosse, C.5
  • 56
    • 4243589450 scopus 로고    scopus 로고
    • Lobeline: A natural product with high affinity for neuronal nicotinic receptors and a vast potential for use in neurological disorders
    • McCurdy, C. R.; Miller, R. L.; Beach, J. W. Lobeline: A natural product with high affinity for neuronal nicotinic receptors and a vast potential for use in neurological disorders. Biolog. Active Nat. Prod., 2000, 151-162.
    • (2000) Biolog. Active Nat. Prod. , pp. 151-162
    • McCurdy, C.R.1    Miller, R.L.2    Beach, J.W.3
  • 57
    • 0028605864 scopus 로고
    • Comparison of the binding of nicotinic agonists to receptors from human and rat cerebral cortex and from chick brain (alpha(4)beta(2) transfected into mouse fibroblasts with ion-channel activity
    • Court, J. A.; Perry, E. K.; Spurden, D.; Lloyd, S.; Gillespie, J. I.; Whiting, P.; Barlow, R. Comparison of the binding of nicotinic agonists to receptors from human and rat cerebral cortex and from chick brain (alpha(4)beta(2) transfected into mouse fibroblasts with ion-channel activity. Brain Res., 1994, 667, 118-122.
    • (1994) Brain Res. , vol.667 , pp. 118-122
    • Court, J.A.1    Perry, E.K.2    Spurden, D.3    Lloyd, S.4    Gillespie, J.I.5    Whiting, P.6    Barlow, R.7
  • 59
    • 0033539051 scopus 로고    scopus 로고
    • Lobeline: Structure-affinity investigation of nicotinic acetylcholinergic receptor binding
    • Flammia, D.; Dukat, M.; Damaj, M. I.; Martin, B.; Glennon, R. A. Lobeline: Structure-affinity investigation of nicotinic acetylcholinergic receptor binding. J. Med. Chem., 1999, 42, 3726-3731.
    • (1999) J. Med. Chem. , vol.42 , pp. 3726-3731
    • Flammia, D.1    Dukat, M.2    Damaj, M.I.3    Martin, B.4    Glennon, R.A.5
  • 60
    • 4243079826 scopus 로고    scopus 로고
    • Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters
    • Miller, D. K.; Crooks, P. A.; Zheng, G. R.; Grinevich, V. P.; Norrholm, S. D.; Dwoskin, L. P. Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters. J Pharmacol. Exp. Ther., 2004, 310, 1035-1045.
    • (2004) J Pharmacol. Exp. Ther. , vol.310 , pp. 1035-1045
    • Miller, D.K.1    Crooks, P.A.2    Zheng, G.R.3    Grinevich, V.P.4    Norrholm, S.D.5    Dwoskin, L.P.6
  • 62
    • 0013915979 scopus 로고
    • Inhibition of gastric contraction following stimulation of intrathoracic sensory endings
    • Bevan, J. A.; Hughes, T. Inhibition of gastric contraction following stimulation of intrathoracic sensory endings. Arch. Int. Pharmacodyn. Ther., 1966, 161, 334-342.
    • (1966) Arch. Int. Pharmacodyn. Ther. , vol.161 , pp. 334-342
    • Bevan, J.A.1    Hughes, T.2
  • 63
    • 0027232237 scopus 로고
    • Nicotinic receptor agonists exhibit anxiolytic-like effects on the elevated plus-maze test
    • Brioni, J. D.; Oneill, A. B.; Kim, D. J. B.; Decker, M. W. Nicotinic receptor agonists exhibit anxiolytic-like effects on the elevated plus-maze test. Eur. J. Pharmacol., 1993, 238, 1-8.
    • (1993) Eur. J. Pharmacol. , vol.238 , pp. 1-8
    • Brioni, J.D.1    Oneill, A.B.2    Kim, D.J.B.3    Decker, M.W.4
  • 64
    • 0027285805 scopus 로고
    • Effects of lobeline, a nicotinic receptor agonist, on learning and memory
    • Decker, M. W.; Majchrzak, M. J.; Arneric, S. P. Effects of lobeline, a nicotinic receptor agonist, on learning and memory. Pharmacol. Biochem. Behav., 1993, 45, 571-576.
    • (1993) Pharmacol. Biochem. Behav. , vol.45 , pp. 571-576
    • Decker, M.W.1    Majchrzak, M.J.2    Arneric, S.P.3
  • 65
    • 0027952501 scopus 로고
    • Hyperalgesic and analgesic actions of morphine, U50-488, naltrexone, and (-)-lobeline in the rat brainstem
    • Hamann, S. R.; Martin, W. R. Hyperalgesic and analgesic actions of morphine, U50-488, naltrexone, and (-)-lobeline in the rat brainstem. Pharmacol. Biochem. Behav., 1994, 47, 197-201.
    • (1994) Pharmacol. Biochem. Behav. , vol.47 , pp. 197-201
    • Hamann, S.R.1    Martin, W.R.2
  • 66
    • 0024455877 scopus 로고
    • Relations between structure and nicotine-like activity-Xray crystal-structure analysis of (-)-cytisine and (-)-lobeline hydrochloride and a comparison with (-)-nicotine and other nicotine-like compounds
    • Barlow, R. B.; Johnson, O. Relations between structure and nicotine-like activity-Xray 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.
    • (1989) Br. J. Pharmacol. , vol.98 , pp. 799-808
    • Barlow, R.B.1    Johnson, O.2
  • 67
    • 0032101052 scopus 로고    scopus 로고
    • Reinforcing effects of nicotinic compounds: Intravenous self-administration in drug-naive mice
    • Rasmussen, T.; Swedberg, M. D. B. Reinforcing effects of nicotinic compounds: Intravenous self-administration in drug-naive mice. Pharmacol. Biochem. Behav., 1998, 60, 567-573.
    • (1998) Pharmacol. Biochem. Behav. , vol.60 , pp. 567-573
    • Rasmussen, T.1    Swedberg, M.D.B.2
  • 69
    • 0023017717 scopus 로고
    • Further studies on nicotine-induced conditioned place preference in the rat
    • Fudala, P. J.; Iwamoto, E. T. Further studies on nicotine-induced conditioned place preference in the rat. Pharmacol. Biochem. Behav., 1986, 25, 1041-1049.
    • (1986) Pharmacol. Biochem. Behav. , vol.25 , pp. 1041-1049
    • Fudala, P.J.1    Iwamoto, E.T.2
  • 70
    • 0028968934 scopus 로고
    • Dissociations between the locomotor stimulant and depressant effects of nicotinic agonists in rats
    • Stolerman, I. P.; Garcha, H. S.; Mirza, N. R. Dissociations between the locomotor stimulant and depressant effects of nicotinic agonists in rats. Psychopharmacology, 1995, 117, 430-437.
    • (1995) Psychopharmacology , vol.117 , pp. 430-437
    • Stolerman, I.P.1    Garcha, H.S.2    Mirza, N.R.3
  • 73
    • 0032440954 scopus 로고    scopus 로고
    • Activation and inhibition of the human alpha 7 nicotinic acetylcholine receptor by agonists
    • Briggs, C. A.; McKenna, D. G. Activation and inhibition of the human alpha 7 nicotinic acetylcholine receptor by agonists. Neuropharmacology, 1998, 37, 1095-1102.
    • (1998) Neuropharmacology , vol.37 , pp. 1095-1102
    • Briggs, C.A.1    McKenna, D.G.2
  • 75
    • 0031595598 scopus 로고    scopus 로고
    • 3H]dopamine from rat striatal synaptic vesicles: Comparison with D-amphetamine
    • 3H]dopamine from rat striatal synaptic vesicles: Comparison with D-amphetamine. J. Neurochem., 1998, 71, 258-265.
    • (1998) J. Neurochem. , vol.71 , pp. 258-265
    • Teng, L.1    Crooks, P.A.2    Dwoskin, L.P.3
  • 76
    • 4243050488 scopus 로고    scopus 로고
    • Effects of methamphetamine and lobeline on vesicular monoamine and dopamine transporter-mediated dopamine release in a cotransfected model system
    • Wilhelm, C. J.; Johnson, R. A.; Lysko, P. G.; Eshleman, A. J.; Janowsky, A. Effects of methamphetamine and lobeline on vesicular monoamine and dopamine transporter-mediated dopamine release in a cotransfected model system. J. Pharmacol. Exp. Ther., 2004, 310, 1142-1151.
    • (2004) J. Pharmacol. Exp. Ther. , vol.310 , pp. 1142-1151
    • Wilhelm, C.J.1    Johnson, R.A.2    Lysko, P.G.3    Eshleman, A.J.4    Janowsky, A.5
  • 77
    • 39749162240 scopus 로고    scopus 로고
    • Lobeline effects on tonic and methamphetamine-induced dopamine release
    • Wilhelm, C. J.; Johnson, R. A.; Eshleman, A. J.; Janowsky, A. Lobeline effects on tonic and methamphetamine-induced dopamine release. Biochem. Pharmacol., 2008, 75, 1411-1415.
    • (2008) Biochem. Pharmacol. , vol.75 , pp. 1411-1415
    • Wilhelm, C.J.1    Johnson, R.A.2    Eshleman, A.J.3    Janowsky, A.4
  • 80
    • 33751269092 scopus 로고    scopus 로고
    • Lobeline attenuates methamphetamine-induced stereotypy in adolescent mice
    • Tatsuta, T.; Kitanaka, N.; Kitanaka, J.; Morita, Y.; Takemura, M. Lobeline attenuates methamphetamine-induced stereotypy in adolescent mice. Neurochem. Res., 2006, 31, 1359-1369.
    • (2006) Neurochem. Res. , vol.31 , pp. 1359-1369
    • Tatsuta, T.1    Kitanaka, N.2    Kitanaka, J.3    Morita, Y.4    Takemura, M.5
  • 81
  • 82
    • 33745945424 scopus 로고    scopus 로고
    • Lobeline augments and inhibits cocaine-induced hyperactivity in rats
    • Polston, J. E.; Cunningham, C. S.; Rodvelt, K. R.; Miller, D. K. Lobeline augments and inhibits cocaine-induced hyperactivity in rats. Life Sci., 2006, 79, 981-990.
    • (2006) Life Sci. , vol.79 , pp. 981-990
    • Polston, J.E.1    Cunningham, C.S.2    Rodvelt, K.R.3    Miller, D.K.4
  • 83
    • 11844260723 scopus 로고    scopus 로고
    • Lobeline attenuates methamphetamine-induced changes in vesicular monoamine transporter 2 immunoreactivity and monoamine depletions in the striatum
    • Eyerman, D. J.; Yamamoto, B. K. Lobeline attenuates methamphetamine-induced changes in vesicular monoamine transporter 2 immunoreactivity and monoamine depletions in the striatum. J. Pharmacol. Exp. Ther., 2005, 312, 160-169.
    • (2005) J. Pharmacol. Exp. Ther. , vol.312 , pp. 160-169
    • Eyerman, D.J.1    Yamamoto, B.K.2
  • 84
    • 34248593694 scopus 로고    scopus 로고
    • Lobeline, a potential pharmacotherapy for drug addiction, binds to mu opioid receptors and diminishes the effects of opioid receptor agonists
    • Miller, D. K.; Lever, J. R.; Rodvelt, K. R.; Baskett, J. A.; Will, M. J.; Kracke, G. R. Lobeline, a potential pharmacotherapy for drug addiction, binds to mu opioid receptors and diminishes the effects of opioid receptor agonists. Drug Alcohol Depend., 2007, 89, 282-291.
    • (2007) Drug Alcohol Depend. , vol.89 , pp. 282-291
    • Miller, D.K.1    Lever, J.R.2    Rodvelt, K.R.3    Baskett, J.A.4    Will, M.J.5    Kracke, G.R.6
  • 85
    • 84981837422 scopus 로고
    • Alkaloids. Ix. Mutarotation of lobeline. cis-trans isomers in the Lobelia alkaloid series
    • Ebnöther, A. Alkaloids. Ix. Mutarotation of lobeline. cis-trans isomers in the Lobelia alkaloid series. Helv. Chim. Acta, 1958, 41, 386-396.
    • (1958) Helv. Chim. Acta , vol.41 , pp. 386-396
    • Ebnöther, A.1
  • 87
    • 33747340517 scopus 로고    scopus 로고
    • Des-keto lobeline analogs with increased potency and selectivity at dopamine and serotonin transporters
    • Zheng, G.; Horton, D. B.; Deaciuc, A. G.; Dwoskin, L. P.; Crooks, P. A. Des-keto lobeline analogs with increased potency and selectivity at dopamine and serotonin transporters. Bioorg. Med. Chem. Lett., 2006, 16, 5018-5021.
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 5018-5021
    • Zheng, G.1    Horton, D.B.2    Deaciuc, A.G.3    Dwoskin, L.P.4    Crooks, P.A.5
  • 88
    • 23944519341 scopus 로고    scopus 로고
    • Defunctionalized lobeline analogues: Structureactivity of novel ligands for the vesicular monoamine transporter
    • Zheng, G.; Dwoskin, L. P.; Deaciuc, A. G.; Norrholm, S. D.; Crooks, P. A. Defunctionalized lobeline analogues: Structureactivity of novel ligands for the vesicular monoamine transporter. J. Med. Chem., 2005, 48, 5551-5560.
    • (2005) J. Med. Chem. , vol.48 , pp. 5551-5560
    • Zheng, G.1    Dwoskin, L.P.2    Deaciuc, A.G.3    Norrholm, S.D.4    Crooks, P.A.5
  • 91
  • 92
    • 56349168456 scopus 로고    scopus 로고
    • Synthesis and evaluation of a series of homologues of lobelane at the vesicular monoamine transporter-2
    • Zheng, G.; Dwoskin, L. P.; Deaciuc, A. G.; Crooks, P. A. Synthesis and evaluation of a series of homologues of lobelane at the vesicular monoamine transporter-2. Bioorg. Med. Chem., 2008, 18, 6509-6512.
    • (2008) Bioorg. Med. Chem. , vol.18 , pp. 6509-6512
    • Zheng, G.1    Dwoskin, L.P.2    Deaciuc, A.G.3    Crooks, P.A.4
  • 93
    • 0033583019 scopus 로고    scopus 로고
    • Asymmetric syntheses of 2-substituted and 2,5-disubstituted pyrrolidines from (3s,5r,7ar)-5-(benzotriazol-1-Yl)-3-phenyl[2,1-B]oxazolopyrrolidine
    • Katritzky, A. R.; Cui, X. L.; Yang, B.; Steel, P. J. Asymmetric syntheses of 2-substituted and 2,5-disubstituted pyrrolidines from (3s,5r,7ar)-5-(benzotriazol-1-Yl)-3-phenyl[2,1-B]oxazolopyrrolidine. J. Org. Chem., 1999, 64, 1979-1985.
    • (1999) J. Org. Chem. , vol.64 , pp. 1979-1985
    • Katritzky, A.R.1    Cui, X.L.2    Yang, B.3    Steel, P.J.4
  • 94
    • 72249105289 scopus 로고    scopus 로고
    • Pyrrolidine Analogs of lobeline: Relationship of Affinity for the dihydrotetrabenazine binding site with function of the vesicular monoamine transporter (VMAT2)
    • Varkat, A. P.; Nickell, J. R.; Chagkutip, J.; Dwoskin, L. P.; Crooks, P. A. Pyrrolidine Analogs of lobeline: relationship of Affinity for the dihydrotetrabenazine binding site with function of the vesicular monoamine transporter (VMAT2). J. Med. Chem., 2009, 52, 7878-7882.
    • (2009) J. Med. Chem. , vol.52 , pp. 7878-7882
    • Varkat, A.P.1    Nickell, J.R.2    Chagkutip, J.3    Dwoskin, L.P.4    Crooks, P.A.5
  • 95
    • 24344445278 scopus 로고    scopus 로고
    • Synthesis and evaluation of a series of tropane analogues as novel vesicular monoamine transporter-2 ligands
    • Zheng, G.; Dwoskin, L. P.; Deaciuc, A. G.; Crooks, P. A. Synthesis and evaluation of a series of tropane analogues as novel vesicular monoamine transporter-2 ligands. Bioorg. Med. Chem. Lett., 2005, 15, 4463-4466.
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 4463-4466
    • Zheng, G.1    Dwoskin, L.P.2    Deaciuc, A.G.3    Crooks, P.A.4
  • 98
    • 0033088080 scopus 로고    scopus 로고
    • The utilization of a neural network system in the diagnosis of appendicitis
    • Shah, D. R.; Dev, V. R.; Brown, C. A. The utilization of a neural network system in the diagnosis of appendicitis. M. D. Comput: Comput. Med. Pract., 1999, 16, 65-67.
    • (1999) M. D. Comput: Comput. Med. Pract. , vol.16 , pp. 65-67
    • Shah, D.R.1    Dev, V.R.2    Brown, C.A.3
  • 99
    • 0036254780 scopus 로고    scopus 로고
    • Assessment of nodal involvement and survival analysis in breast cancer patients using image cytometric data: Statistical, neural network and fuzzy approaches
    • Seker, H.; Odetayo, M. O.; Petrovic, D.; Naguib, R. N. G.; Bartoli, C.; Alasio, L.; Lakshmi, M. S.; Sherbet, G. V. Assessment of nodal involvement and survival analysis in breast cancer patients using image cytometric data: statistical, neural network and fuzzy approaches. Anticancer Res., 2002, 22, 433-438.
    • (2002) Anticancer Res. , vol.22 , pp. 433-438
    • Seker, H.1    Odetayo, M.O.2    Petrovic, D.3    Naguib, R.N.G.4    Bartoli, C.5    Alasio, L.6    Lakshmi, M.S.7    Sherbet, G.V.8
  • 100
    • 0036116178 scopus 로고    scopus 로고
    • Applications of artificial neural networks in AIDS research and therapy
    • Sardari, S.; Sardari, D. Applications of artificial neural networks in AIDS research and therapy. Curr. Pharm. Des., 2002, 8, 659-670.
    • (2002) Curr. Pharm. Des. , vol.8 , pp. 659-670
    • Sardari, S.1    Sardari, D.2
  • 102
    • 0038069350 scopus 로고    scopus 로고
    • Neural networks for effect prediction in environmental and health issues using large datasets
    • Kaiser, K. L. E. Neural networks for effect prediction in environmental and health issues using large datasets. Quant. Struct. Act. Relat., 2003, 22, 1-6.
    • (2003) Quant. Struct. Act. Relat. , vol.22 , pp. 1-6
    • Kaiser, K.L.E.1
  • 103
    • 33644974211 scopus 로고    scopus 로고
    • QSAR modeling of mono-and bis-quanternary ammonium salts that act as antagonists at neuronal nicotinic acetylcholine receptors mediating dopamine release
    • Zheng, F.; Bayram, E.; Sumithran, S. P.; Ayers, J. T.; Zhan, C.-G.; Schmitt, J. D.; Dwoskin, L. P.; Crooks, P. A. QSAR modeling of mono-and bis-quanternary ammonium salts that act as antagonists at neuronal nicotinic acetylcholine receptors mediating dopamine release. Bioorg. Med. Chem., 2006, 14, 3017-3037.
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 3017-3037
    • Zheng, F.1    Bayram, E.2    Sumithran, S.P.3    Ayers, J.T.4    Zhan, C.-G.5    Schmitt, J.D.6    Dwoskin, L.P.7    Crooks, P.A.8
  • 105
    • 0030900210 scopus 로고    scopus 로고
    • Neural network modeling for estimation of the aqueous solubility of structurally related drugs
    • Huuskonen, J.; Salo, M.; Taskinen, J. Neural network modeling for estimation of the aqueous solubility of structurally related drugs. J. Pharm. Sci., 1997, 86, 450-454.
    • (1997) J. Pharm. Sci. , vol.86 , pp. 450-454
    • Huuskonen, J.1    Salo, M.2    Taskinen, J.3
  • 106
    • 33646420101 scopus 로고    scopus 로고
    • Statistical learning approach for predicting specific pharmacodynamic, pharmacokinetic, or toxicological properties of pharmaceutical agents
    • Li, H.; Yap, C. W.; Xue, Y.; Li, Z. R.; Ung, C. Y.; Han, L. Y.; Chen, Y. Z. Statistical learning approach for predicting specific pharmacodynamic, pharmacokinetic, or toxicological properties of pharmaceutical agents. Drug Dev. Res., 2005, 66, 245-259.
    • (2005) Drug Dev. Res. , vol.66 , pp. 245-259
    • Li, H.1    Yap, C.W.2    Xue, Y.3    Li, Z.R.4    Ung, C.Y.5    Han, L.Y.6    Chen, Y.Z.7
  • 107
    • 30544446631 scopus 로고    scopus 로고
    • Mapping the dose-effect relationship of orbofiban from sparse data with an artificial neural network
    • Mager, D. E.; Shirey, J. D.; Cox, D.; Fitzgerald, D. J.; Abernethy, D. R. Mapping the dose-effect relationship of orbofiban from sparse data with an artificial neural network. J. Pharm. Sci., 2005, 94, 2475-2486.
    • (2005) J. Pharm. Sci. , vol.94 , pp. 2475-2486
    • Mager, D.E.1    Shirey, J.D.2    Cox, D.3    Fitzgerald, D.J.4    Abernethy, D.R.5
  • 108
    • 33947103708 scopus 로고    scopus 로고
    • Computational neural network analysis of the affinity of lobeline and tetrabenazine analogs for the vesicular monoamine transporter-2
    • Zheng, F.; Zheng, G. R.; Deaciuc, A. G.; Zhan, C.-G.; Dwoskin, L. P.; Crooks, P. A. Computational neural network analysis of the affinity of lobeline and tetrabenazine analogs for the vesicular monoamine transporter-2. Bioorg. Med. Chem., 2007, 15, 2975-2992
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 2975-2992
    • Zheng, F.1    Zheng, G.R.2    Deaciuc, A.G.3    Zhan, C.-G.4    Dwoskin, L.P.5    Crooks, P.A.6


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