Bakuchiol analogs inhibit monoamine transporters and regulate monoaminergic functions

Biochemical Pharmacology

Volumn 75, Issue 9, 2008, Pages 1835-1847

  Zhao, Gang ^a,b   Zang, Shao Yun ^a   Zheng, Xiang Wei ^b   Zhang, Xiao Hua ^b   Guo, Li He ^a,b  

^a Cell Star Bio Technologies Co Limited   (China)

^b INSTITUTE OF BIOCHEMISTRY AND CELL BIOLOGY   (China)

Author keywords

Bakuchiol analogs; Dopamine transporter; Monoamine transporter; Norepinephrine transporter; Reuptake inhibitor

Indexed keywords

1 [2 (BENZHYDRYLOXY)ETHYL] 4 (3 PHENYLPROPYL)PIPERAZINE; 1 METHYL 4 PHENYLPYRIDINIUM; AMFEBUTAMONE; BAKUCHIOL; DELTA1,3 HYDROXYBAKUCHIOL; DELTA3,2 HYDROXYBAKUCHIOL; DOPAMINE TRANSPORTER; NORADRENALIN TRANSPORTER; RESERPINE; SEROTONIN TRANSPORTER; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; C57BL 6 MOUSE; CELL CULTURE; CHO CELL; COCAINE DEPENDENCE; CONTROLLED STUDY; CULTURE MEDIUM; DEPRESSION; DOPAMINERGIC TRANSMISSION; DRUG EFFECT; DRUG EFFICACY; DRUG ISOLATION; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; FRUIT; IC 50; MALE; MOUSE; NEUROTRANSMISSION; NONHUMAN; PARKINSON DISEASE; PLACE PREFERENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; PSORALEA; SCORING SYSTEM;

ANIMALS; BIOGENIC MONOAMINES; CELL SURVIVAL; CHO CELLS; CONDITIONING, CLASSICAL; CRICETINAE; CRICETULUS; FRUIT; HUMANS; MALE; MICE; MICE, INBRED C57BL; MOTOR ACTIVITY; NEUROTRANSMITTER TRANSPORT PROTEINS; PHENOLS; PLANT EXTRACTS; PSORALEA; RATS; RATS, SPRAGUE-DAWLEY; SYNAPTOSOMES; TRANSFECTION;

EID: 41949120721     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2008.01.014     Document Type: Article

References (46)

1. Torres G.E. The dopamine transporter proteome. J Neurochem 97 suppl. 1 (2006) 3-10
2. Gainetdinov R.R., and Caron M.G. Monoamine transporters: from genes to behavior. Annu Rev Pharmacol Toxicol 43 (2003) 261-284
3. Hersch S.M., Yi H., Heilman C.J., Edwards R.H., and Levey A.I. Subcellular locallization and molecular topology of dopamine transporter in the striatum and substantia nigra. J Comp Neurol 388 (1997) 211-227
4. - neurotransmitter transporters. J Neurochem 71 (1998) 1785-1803
5. Miller G.W., Gaintedinov R.R., Levey A.I., and Caron M.G. Dopamine transporters and neuronal injury. Trends Pharmacol Sci 20 (1999) 424-429
6. Greengard P. The neurobiology of slow synaptic transmission. Science 294 (2001) 1024-1030
7. +-induced dopaminergic nigrostriatal injury in rat. J Neurochem 80 (2002) 365-374
8. Berretta N., Freestone P.S., Guatteo E., de Castro D., Geracitano R., Bernardi G., et al. Acute effects of 6-hydroxydopamine on dopaminergic neurons of the rat substantia nigra pars compacta in vitro. Neurotoxicology 26 (2005) 869-881
9. Kuter K., Smialowska M., Wieronska J., Zieba B., Wardas J., Pietraszek M., et al. Toxic influence of subchronic paraquat administration on dopaminergic neurons in rats. Brain Res 1155 (2007) 196-207
10. Jayanthi L.D., and Ramamoorthy S. Regulation of monoamine transporters: influence of psychostimulants and therapeutic antidepressants. AAP 7 (2005) E728-E738
11. Howell L.L., and Kimmel H.L. Monoamine transporters and psychostimulant addiction. Biochem Pharmacol 75 (2008) 196-217
12. Amara S.G., and Sonders M.S. Neurotransmitter transporters as molecular targets for addictive drugs. Drug Alcohol Depend 51 (1998) 87-96
13. Schroeter S., Apparsundaram S., Wiley R.G., Miner L.H., Sesack S.R., and Blakely R.D. Immunolocalization of the cocaine- and antidepressant-sensitive l-norepinephrine transporter. J Comp Neurol 420 (2000) 211-232
14. Zhao G., Li S., Qin G.W., Fei J., and Guo L.H. Inhibitive effects of Fructus Psoraleae extract on dopamine transporter and noradrenaline transporter. J Ethnopharmacol 112 (2007) 498-506
15. Xu L.F., Chu W.J., Qing X.Y., Li S., Wang X.S., Qing G.W., et al. Protopine inhibits serotonin transporter and noradrenaline transporter and has the antidepressant-like effect in mice models. Neuropharmacology 50 (2006) 934-940
16. Kokoshka J.M., Metzger R.R., Wilkins D.G., Gibb J.W., Hanson G.R., and Fleckenstein A.E. Methamphetamine treatment rapidly inhibits serotonin, but not glutamate, transporters in rat brain. Brain Res 799 (1998) 78-83
17. Maldonado R., Saiardi A., Valverde O., Samad T.A., Roques B.P., and Borrelli E. Absence of opiate rewarding effects in mice lacking dopamine D2 receptors. Nature 388 (1997) 586-589
18. Schonn J.S., Desnos C., Henry J.P., and Darchen F. Transmitter uptake and release in PC12 cells overexpressing plasma membrane monoamine transporters. J Neurochem 84 (2003) 669-677
19. Scholze P., Nørregaard L., Singer E.A., Freissmuth M., Gether U., and Sitte H.H. The role of zinc ions in reverse transport mediated by monoamine transporters. J Biol Chem 277 (2002) 21505-21513
20. Becker D.E. Drug therapy in dental practice: general principles: part 2. Pharmacodynamic considerations. Anesth Prog 54 (2007) 19-23
21. Oates J.A. The science of drug therapy. In: Brunton L.L., Lazo J.S., and Parker K.L. (Eds). Goodman and Gilman's the pharmacological basis of therapeutics. 11th ed. (2006), McGraw-Hill, New York 117-136
22. Ding J., Shi J., Cui D., Xu L., Duan S., Guo L., et al. Development of peptidic dopamine transporter inhibitors via aromatic modification-mediated conformational restriction. J Med Chem 49 (2006) 4048-4051
23. Stuber G.D., Roitman M.F., Phillips P.E., Carelli R.M., and Wightman R.M. Rapid dopamine signaling in the nucleus accumbens during contingent and noncontingent cocaine administration. Neuropsychopharmacology 30 (2005) 853-863
24. Kawai H., Makino Y., Hirobe M., and Ohta S. Novel endogenous 1,2,3,4-tetrahydroisoquinoline derivatives: uptake by dopamine transporter and activity to induce parkinsonism. J Neurochem 70 (1998) 745-751
25. Storch A., Hwang Y.I., Gearhart D.A., Beach J.W., Neafsey E.J., Collins M.A., et al. Dopamine transporter-mediated cytotoxicity of β-carbolinium derivatives related to Parkinson's disease: relationship to transporter-dependent uptake. J Neurochem 89 (2004) 685-694
26. + opens the mitochondrial permeability transition pore and releases cytochrome c in isolated mitochondria via an oxidative mechanism. Acta Biochim Biophys Sin 1453 (1999) 49-62
27. Vila M., Vukosavic S., Jackson-Lewis V., Neystat M., Jakowec M., and Przedborski S. α-Synuclein up-regulation in substantia nigra dopaminergic neurons following administration of parkinsonian toxin MPTP. J Neurochem 74 (2000) 721-729
28. Desai R.I., Kopajtic T.A., Koffarnus M., Newman A.H., and Katz J.L. Identification of a dopamine transporter ligand that blocks the stimulant effects of cocaine. J Neurosci 25 (2005) 1889-1893
29. Florin S.M., Kuczenski R., and Segal D.S. Effects of reserpine on extracellular caudate dopamine and hippocampus norepinephrine responses to amphetamine and cocaine: mechanistic and behavioral considerations. J Pharmacol Exp Ther 274 (1995) 231-241
30. Marino M.J., Williams Jr. D.L., O'Brien J.A., Valenti O., McDonald T.P., Clements M.K., et al. Allosteric modulation of group III metabotropic glutamate receptor 4: a potential approach to Parkinson's disease treatment. Proc Natl Acad Sci USA 100 (2003) 13668-13673
31. Newton S.M., Lau C., Gurcha S.S., Besra G.S., and Wright C.W. The evaluation of forty-three plant species for in vitro antimycobacterial activities: isolation of active constituents from Psoralea corylifolia and Sanguinaria canadensis. J Ethnopharmacol 79 (2002) 57-67
32. Haraguchi H., Inoue J., Tamura Y., and Mizutani K. Antioxidative components of Psoralea corylifolia (Leguminosae). Phytother Res 16 (2002) 539-544
33. Park E.J., Zhao Y.Z., Kim Y.C., and Sohn D.H. Protective effect of (S)-bakuchiol from Psoralea corylifolia on rat liver injury in vitro and in vivo. Planta Med 71 (2005) 508-513
34. 2-terminal kinase-mediated mitochondrial translocation of Bax in rat liver myofibroblasts. Eur J Pharmacol 559 (2007) 115-123
35. Labbe C., Faini F., Coll J., and Conolly J.D. Bakuchiol derivatives from the leaves of Psoralea glandulosa. Phytochemistry 42 (1996) 1299-1303
36. Matsuda H., Sugimoto S., Morikawa T., Matsuhira K., Mizuguchi E., Nakamura S., et al. Bioactive constituents from Chinese natural medicines: XX. Inhibitors of antigen-induced degranulation in RBL-2H3 cells from the seeds of Psoralea corylifolia. Chem Pharm Bull (Tokyo) 55 (2007) 106-110
37. Torres G.E., Gainetdinov R.R., and Caron M.G. Plasma membrane monoamine transporters: structure, regulation and function. Nat Rev Neurosci 4 (2003) 13-25
38. Adinoff B. Neurobiologic processes in drug reward and addiction. Harv Rev Psychiatry 12 (2004) 305-320
39. Morton D.B., and Bredt D.S. Norepinephrine increases cyclic GMP levels in cerebellar cells from neuronal nitric oxide synthase knockout mice. J Neurochem 71 (1998) 440-443
40. 2C-adrenoceptor density in the cerebral cortex during postnatal life and impairs neocortical long-term potentiation and visuo-spatial performance in rats. J Neurochem 93 (2005) 1099-1109
41. Troadec J.D., Marien M., Darios F., Hartmann A., Ruberg M., Colpaert F., et al. Noradrenaline provides long-term protection to dopaminergic neurons by reducing oxidative stress. J Neurochem 79 (2001) 200-210
42. Laifenfeld D., Klein E., and Ben-Shachar D. Norepinephrine alters the expression of genes involved in neuronal sprouting and differentiation: relevance for major depression and antidepressant mechanisms. J Neurochem 83 (2002) 1054-1064
43. Kalinin S., Gavrilyuk V., Polak P.E., Vasser R., Zhao J., Heneka M.T., et al. Noradrenaline deficiency in brain increases β-amyloid plaque burden in an animal model of Alzheimer's disease. Neurobiol Aging 28 (2007) 1206-1214
44. Archer T., and Fredriksson A. Influence of noradrenaline denervation on MPTP-induced deficits in mice. J Neural Transm 113 (2006) 1119-1129
45. Carboni E., Silvagni A., Vacca C., and Di Chiara G. Cumulative effect of norepinephrine and dopamine carrier blockade on extracellular dopamine increase in the nucleus accumbens shell, bed nucleus of stria terminalis and prefrontal cortex. J Neurochem 96 (2006) 473-481
46. Rommelfanger K.S., Weinshenker D., and Miller G.W. Reduced MPTP toxicity in noradrenaline transporter knockout mice. J Neurochem 91 (2004) 1116-1124