Lobelane Analogues As Novel Ligands for the Vesicular Monoamine Transporter-2

Overview

Journal Bioorg Med Chem

Specialties Biochemistry
Chemistry

Date 2005 May 25

PMID 15911306

Citations 18

Authors

Guangrong Zheng

Linda P Dwoskin

Agripina G Deaciuc

Jun Zhu

Marlon D Jones

Peter A Crooks

Affiliations

Soon will be listed here.

Abstract

A series of lobelane analogues has been synthesized and their structure-activity relationships at the vesicular monoamine transporter-2 (VMAT2) have been evaluated. The most potent analogues in this series were the cis-2,6-piperidino analogues, 25b, 27b, 28b, and 30b, with K(i) values ranging from 430 to 580 nM.

Citing Articles

GZ-793A inhibits the neurochemical effects of methamphetamine via a selective interaction with the vesicular monoamine transporter-2.

Nickell J, Siripurapu K, Horton D, Zheng G, Crooks P, Dwoskin L Eur J Pharmacol. 2016; 795:143-149.

PMID: 27986625 PMC: 7050634. DOI: 10.1016/j.ejphar.2016.12.016.

1,4-Diphenalkylpiperidines: A new scaffold for the design of potent inhibitors of the vesicular monoamine transporter-2.

Nickell J, Culver J, Janganati V, Zheng G, Dwoskin L, Crooks P Bioorg Med Chem Lett. 2016; 26(13):2997-3000.

PMID: 27212067 PMC: 4946565. DOI: 10.1016/j.bmcl.2016.05.025.

Lobelane analogues containing 4-hydroxy and 4-(2-fluoroethoxy) aromatic substituents: Potent and selective inhibitors of [(3)H]dopamine uptake at the vesicular monoamine transporter-2.

Joolakanti S, Nickell J, Janganati V, Zheng G, Dwoskin L, Crooks P Bioorg Med Chem Lett. 2016; 26(10):2422-2427.

PMID: 27080180 PMC: 4977194. DOI: 10.1016/j.bmcl.2016.03.119.

Synthesis of Lobeline, Lobelane and their Analogues. A Review.

Zheng G, Crooks P Org Prep Proced Int. 2016; 47(5):317-337.

PMID: 26858465 PMC: 4743053. DOI: 10.1080/00304948.2015.1066642.

The vesicular monoamine transporter-2: an important pharmacological target for the discovery of novel therapeutics to treat methamphetamine abuse.

Nickell J, Siripurapu K, Vartak A, Crooks P, Dwoskin L Adv Pharmacol. 2014; 69:71-106.

PMID: 24484975 PMC: 4084610. DOI: 10.1016/B978-0-12-420118-7.00002-0.

References

Dwoskin L, Crooks P . A novel mechanism of action and potential use for lobeline as a treatment for psychostimulant abuse. Biochem Pharmacol. 2002; 63(2):89-98. DOI: 10.1016/s0006-2952(01)00899-1. View

Wise R . Brain reward circuitry: insights from unsensed incentives. Neuron. 2002; 36(2):229-40. DOI: 10.1016/s0896-6273(02)00965-0. View

Lee L, Vander Borght T, Sherman P, Frey K, Kilbourn M . In vitro and in vivo studies of benzisoquinoline ligands for the brain synaptic vesicle monoamine transporter. J Med Chem. 1996; 39(1):191-6. DOI: 10.1021/jm950117b. View

Pifl C, Drobny H, Reither H, Hornykiewicz O, Singer E . Mechanism of the dopamine-releasing actions of amphetamine and cocaine: plasmalemmal dopamine transporter versus vesicular monoamine transporter. Mol Pharmacol. 1995; 47(2):368-73. View

Zheng G, Dwoskin L, Crooks P . 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(24):8514-7. PMC: 3597091. DOI: 10.1021/jo048848j. View

Miller D, Crooks P, Zheng G, Grinevich V, Norrholm S, Dwoskin L . Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters. J Pharmacol Exp Ther. 2004; 310(3):1035-45. DOI: 10.1124/jpet.104.068098. View

Lautens M, Yoshida M . Rhodium-catalyzed addition of arylboronic acids to alkynyl aza-heteroaromatic compounds in water. J Org Chem. 2003; 68(3):762-9. DOI: 10.1021/jo0205255. View

Miller D, Harrod S, Green T, Wong M, Bardo M, Dwoskin L . Lobeline attenuates locomotor stimulation induced by repeated nicotine administration in rats. Pharmacol Biochem Behav. 2002; 74(2):279-86. DOI: 10.1016/s0091-3057(02)00996-6. View

Miller D, Crooks P, Dwoskin L . Lobeline inhibits nicotine-evoked [(3)H]dopamine overflow from rat striatal slices and nicotine-evoked (86)Rb(+) efflux from thalamic synaptosomes. Neuropharmacology. 2000; 39(13):2654-62. DOI: 10.1016/s0028-3908(00)00140-4. View

10.

Sulzer D, Chen T, Lau Y, Kristensen H, Rayport S, Ewing A . Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995; 15(5 Pt 2):4102-8. PMC: 6578196. View

11.

Nordahl T, Salo R, Leamon M . Neuropsychological effects of chronic methamphetamine use on neurotransmitters and cognition: a review. J Neuropsychiatry Clin Neurosci. 2003; 15(3):317-25. DOI: 10.1176/jnp.15.3.317. View

12.

Cheng Y, Prusoff W . Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol. 1973; 22(23):3099-108. DOI: 10.1016/0006-2952(73)90196-2. View

13.

Perera R, Wimalasena D, Wimalasena K . Characterization of a series of 3-amino-2-phenylpropene derivatives as novel bovine chromaffin vesicular monoamine transporter inhibitors. J Med Chem. 2003; 46(13):2599-605. DOI: 10.1021/jm030004p. View

14.

Teng L, Crooks P, Sonsalla P, Dwoskin L . 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(3):1432-44. View

15.

Terry Jr A, Williamson R, Gattu M, Beach J, McCurdy C, Sparks J . Lobeline and structurally simplified analogs exhibit differential agonist activity and sensitivity to antagonist blockade when compared to nicotine. Neuropharmacology. 1998; 37(1):93-102. DOI: 10.1016/s0028-3908(97)00142-1. View

16.

Harrod S, Dwoskin L, Green T, Gehrke B, Bardo M . Lobeline does not serve as a reinforcer in rats. Psychopharmacology (Berl). 2002; 165(4):397-404. DOI: 10.1007/s00213-002-1289-6. View

17.

Harrod S, Dwoskin L, Crooks P, Klebaur J, Bardo M . Lobeline attenuates d-methamphetamine self-administration in rats. J Pharmacol Exp Ther. 2001; 298(1):172-9. View

18.

Teng L, Crooks P, Dwoskin L . Lobeline displaces [3H]dihydrotetrabenazine binding and releases [3H]dopamine from rat striatal synaptic vesicles: comparison with d-amphetamine. J Neurochem. 1998; 71(1):258-65. DOI: 10.1046/j.1471-4159.1998.71010258.x. View

19.

Miller D, Crooks P, Teng L, Witkin J, Munzar P, Goldberg S . Lobeline inhibits the neurochemical and behavioral effects of amphetamine. J Pharmacol Exp Ther. 2001; 296(3):1023-34. View

20.

Flammia D, Dukat M, Damaj M, Martin B, Glennon R . Lobeline: structure-affinity investigation of nicotinic acetylcholinergic receptor binding. J Med Chem. 1999; 42(18):3726-31. DOI: 10.1021/jm990286m. View