Interactions of cathinone NPS with human transporters and receptors in transfected cells

Current Topics in Behavioral Neurosciences

Volumn 32, Issue , 2017, Pages 49-72

  Simmler, Linda D ^a   Liechti, Matthias E ^a  

^a UNIVERSITY HOSPITAL BASEL   (Switzerland)

Author keywords

Cathinones; Efflux; Heterologous expression systems; In vitro; New psychoactive substances; Pharmacology; Transporters; Uptake

Indexed keywords

AMINOINDANE DERIVATIVE; BENZOFURAN DERIVATIVE; BENZYLPIPERAZINE DERIVATIVE; CARRIER PROTEINS AND BINDING PROTEINS; CATHINONE; COCAINE; CYCLIC AMP; DOPAMINE 1 RECEPTOR; DOPAMINE 2 RECEPTOR; DOPAMINE 3 RECEPTOR; DOPAMINE TRANSPORTER; G PROTEIN COUPLED RECEPTOR; LYSERGIDE; METHAMPHETAMINE; MIDOMAFETAMINE; MONOAMINE; NEUROTRANSMITTER; PSYCHEDELIC AGENT; PSYCHOTROPIC AGENT; RECEPTOR; SEROTONIN 2A RECEPTOR; SEROTONIN TRANSPORTER; TRANSPORTER; UNCLASSIFIED DRUG; VESICULAR MONOAMINE TRANSPORTER; ADRENERGIC RECEPTOR AFFECTING AGENT; ALKALOID; CENTRAL STIMULANT AGENT; DOPAMINE; DOPAMINE UPTAKE INHIBITOR; NORADRENALIN; NORADRENALIN TRANSPORTER; SEROTONIN; SEROTONIN UPTAKE INHIBITOR;

BINDING AFFINITY; BINDING SITE; DRUG RECEPTOR BINDING; DRUG TRANSPORT; EXPERIMENTAL SEROTONIN SYNDROME; GENETIC TRANSFECTION; HUMAN; IC50; METABOLITE; NEUROTRANSMISSION; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; SYNAPTIC MEMBRANE; ANTAGONISTS AND INHIBITORS; DRUG EFFECTS; IN VITRO STUDY; METABOLISM;

ADRENERGIC UPTAKE INHIBITORS; ALKALOIDS; CENTRAL NERVOUS SYSTEM STIMULANTS; DOPAMINE; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; DOPAMINE UPTAKE INHIBITORS; HUMANS; IN VITRO TECHNIQUES; NOREPINEPHRINE; NOREPINEPHRINE PLASMA MEMBRANE TRANSPORT PROTEINS; SEROTONIN; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS; SEROTONIN UPTAKE INHIBITORS;

EID: 85017508714     PISSN: 18663370     EISSN: 18663389     Source Type: Book Series    
DOI: 10.1007/7854_2016_20     Document Type: Chapter

References (91)

1. EMCDDA (2015). European Drug Report 2015. Luxembourg: European Monitoring Centre for Drugs and Drug Addiction (EMCDDA)
2. Liechti M (2015) Novel psychoactive substances (designer drugs): overview and pharmacology of modulators of monoamine signaling. Swiss Med Wkly 145:w14043
3. Rickli A, Hoener MC, Liechti ME (2015) Monoamine transporter and receptor interaction profiles of novel psychoactive substances: para-halogenated amphetamines and pyrovalerone cathinones. Eur Neuropsychopharmacol 25:365-376
4. Simmler L, Buser T, Donzelli M, Schramm Y, Dieu LH, Huwyler J et al (2013) Pharmacological characterization of designer cathinones in vitro. Br J Pharmacol 168:458-470
5. Simmler LD, Rickli A, Hoener MC, Liechti ME (2014) Monoamine transporter and receptor interaction profiles of a new series of designer cathinones. Neuropharmacology 79:152-160
6. Baumann MH, Ayestas MA Jr, Partilla JS, Sink JR, Shulgin AT, Daley PF et al (2012) The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue. Neuropsychopharmacology 37:1192-1203
7. Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M et al (2013) Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive’bath salts’ products. Neuropsychopharmacology 38:552-562
8. Iversen L, Gibbons S, Treble R, Setola V, Huang XP, Roth BL (2013) Neurochemical profiles of some novel psychoactive substances. Eur J Pharmacol 700:147-151
9. Ramamoorthy S, Bauman AL, Moore KR, Han H, Yang-Feng T, Chang AS et al (1993) Antidepressant- and cocaine-sensitive human serotonin transporter: molecular cloning, expression, and chromosomal localization. Proc Natl Acad Sci U S A 90:2542-2546
10. Revel FG, Moreau JL, Gainetdinov RR, Bradaia A, Sotnikova TD, Mory R et al (2011) TAAR1 activation modulates monoaminergic neurotransmission, preventing hyperdopaminergic and hypoglutamatergic activity. Proc Natl Acad Sci U S A 108:8485-8490
11. Tatsumi M, Groshan K, Blakely RD, Richelson E (1997) Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol 340:249-258
12. Groskreutz D, Schenborn ET (1997) Reporter systems. Methods Mol Biol 63:11-30
13. Chaudhary S, Pak JE, Gruswitz F, Sharma V, Stroud RM (2012) Overexpressing human membrane proteins in stably transfected and clonal human embryonic kidney 293S cells. Nat Protoc 7:453-466
14. Henry LK, Field JR, Adkins EM, Parnas ML, Vaughan RA, Zou MF et al (2006) Tyr-95 and Ile-172 in transmembrane segments 1 and 3 of human serotonin transporters interact to establish high affinity recognition of antidepressants. J Biol Chem 281:2012-2023
15. Ran FA, Hsu PD, Wright J, Agarwala V, Scott DA, Zhang F (2013) Genome engineering using the CRISPR-Cas9 system. Nat Protoc 8:2281-2308
16. Chamba A, Holder MJ, Barnes NM, Gordon J (2008) Characterisation of the endogenous human peripheral serotonin transporter SLC6A4 reveals surface expression without N-glycosylation. J Neuroimmunol 204:75-84
17. Marazziti D, Mandillo S, Di Pietro C, Golini E, Matteoni R, Tocchini-Valentini GP (2007) GPR37 associates with the dopamine transporter to modulate dopamine uptake and behavioral responses to dopaminergic drugs. Proc Natl Acad Sci U S A 104:9846-9851
18. Maguire JJ, Kuc RE, Davenport AP (2012) Radioligand binding assays and their analysis. Methods Mol Biol 897:31-77
19. Zhang R, Xie X (2012) Tools for GPCR drug discovery. Acta Pharmacol Sin 33:372-384
20. Tate CG (2012) A crystal clear solution for determining G-protein-coupled receptor structures. Trends Biochem Sci 37:343-352
21. Burlingham BT, Widlanski TS (2003) An intuitive look at the relationship of K-i and IC50: A more general use for the Dixon plot. J Chem Educ 80:214-218
22. Cheng Y, 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
23. Bang-Andersen B, Ruhland T, Jorgensen M, Smith G, Frederiksen K, Jensen KG et al (2011) Discovery of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine (Lu AA21004): a novel multimodal compound for the treatment of major depressive disorder. J Med Chem 54:3206-3221
24. Mazei-Robison MS, Bowton E, Holy M, Schmudermaier M, Freissmuth M, Sitte HH et al (2008) Anomalous dopamine release associated with a human dopamine transporter coding variant. J Neurosci 28:7040-7046
25. Prasad HC, Zhu CB, McCauley JL, Samuvel DJ, Ramamoorthy S, Shelton RC et al (2005) Human serotonin transporter variants display altered sensitivity to protein kinase G and p38 mitogen-activated protein kinase. Proc Natl Acad Sci U S A 102:11545-11550
26. Prosser RA, Stowie A, Amicarelli M, Nackenoff AG, Blakely RD, Glass JD (2014) Cocaine modulates mammalian circadian clock timing by decreasing serotonin transport in the SCN. Neuroscience 275:184-193
27. Thompson BJ, Jessen T, Henry LK, Field JR, Gamble KL, Gresch PJ et al (2011) Transgenic elimination of high-affinity antidepressant and cocaine sensitivity in the presynaptic serotonin transporter. Proc Natl Acad Sci U S A 108:3785-3790
28. Mergy MA, Gowrishankar R, Gresch PJ, Gantz SC, Williams J, Davis GL et al (2014) The rare DAT coding variant Val559 perturbs DA neuron function, changes behavior, and alters in vivo responses to psychostimulants. Proc Natl Acad Sci U S A 111:E4779-E4788
29. Barker EL, Blakely RD (1996) Identification of a single amino acid, phenylalanine 586, that is responsible for high affinity interactions of tricyclic antidepressants with the human serotonin transporter. Mol Pharmacol 50:957-965
30. Wilhelm BG, Mandad S, Truckenbrodt S, Krohnert K, Schafer C, Rammner B et al (2014) Composition of isolated synaptic boutons reveals the amounts of vesicle trafficking proteins. Science 344:1023-1028
31. Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI et al (2001) Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin. Synapse 39:32-41
32. Rothman RB, Lewis B, Dersch C, Xu H, Radesca L, de Costa BR et al (1993) Identification of a GBR12935 homolog, LR1111, which is over 4,000-fold selective for the dopamine transporter, relative to serotonin and norepinephrine transporters. Synapse 14:34-39
33. de la Torre R, Farre M, Ortuno J, Mas M, Brenneisen R, Roset PN et al (2000) Non-linear pharmacokinetics of MDMA (‘ecstasy’) in humans. Br J Clin Pharmacol 49:104-109
34. Mueller DM, Rentsch KM (2012) Generation of metabolites by an automated online metabolism method using human liver microsomes with subsequent identification by LC-MS(n), and metabolism of 11 cathinones. Anal Bioanal Chem 402:2141-2151
35. Rickli A, Kopf S, Hoener MC, Liechti ME (2015) Pharmacological profile of novel psychoactive benzofurans. Br J Pharmacol 172:3412-3425
36. Torok M, Huwyler J, Drewe J, Gutmann H, Fricker G (1998) Transport of the beta-lactam antibiotic benzylpenicillin and the dipeptide glycylsarcosine by brain capillary endothelial cells in vitro. Drug Metab Dispos 26:1144-1148
37. Ukairo OT, Ramanujapuram S, Surratt CK (2007) Fluctuation of the dopamine uptake inhibition potency of cocaine, but not amphetamine, at mammalian cells expressing the dopamine transporter. Brain Res 1131:68-76
38. Hilber B, Scholze P, Dorostkar MM, Sandtner W, Holy M, Boehm S et al (2005) Serotonin-transporter mediated efflux: a pharmacological analysis of amphetamines and non-amphetamines. Neuropharmacology 49:811-819
39. Khoshbouei H, Wang H, Lechleiter JD, Javitch JA, Galli A (2003) Amphetamine-induced dopamine efflux. A voltage-sensitive and intracellular Na+-dependent mechanism. J Biol Chem 278:12070-12077
40. Verrico CD, Miller GM, Madras BK (2007) MDMA (Ecstasy) and human dopamine, norepinephrine, and serotonin transporters: implications for MDMA-induced neurotoxicity and treatment. Psychopharmacology (Berl) 189:489-503
41. Hysek CM, Simmler LD, Nicola VG, Vischer N, Donzelli M, Krahenbuhl S et al (2012) Duloxetine inhibits effects of MDMA (“Ecstasy”) in vitro and in humans in a randomized placebo-controlled laboratory study. PLoS One 7, e36476
42. Scholze P, Zwach J, Kattinger A, Pifl C, Singer EA, Sitte HH (2000) Transporter-mediated release: a superfusion study on human embryonic kidney cells stably expressing the human serotonin transporter. J Pharmacol Exp Ther 293:870-878
43. Pifl C, Drobny H, Reither H, Hornykiewicz O, 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
44. Raiteri M, Angelini F, Levi G (1974) A simple apparatus for studying the release of neurotransmitters from synaptosomes. Eur J Pharmacol 25:411-414
45. Johnson RA, Eshleman AJ, Meyers T, Neve KA, Janowsky A (1998) [3H]substrate- and cell-specific effects of uptake inhibitors on human dopamine and serotonin transporter-mediated efflux. Synapse 30:97-106
46. Marcusson JO, Backstrom IT, Ross SB (1986) Single-site model of the neuronal 5-hydroxytryptamine uptake and imipramine-binding site. Mol Pharmacol 30:121-128
47. Nelson PJ, Rudnick G (1979) Coupling between platelet 5-hydroxytryptamine and potassium transport. J Biol Chem 254:10084-10089
48. Talvenheimo J, Nelson PJ, Rudnick G (1979) Mechanism of imipramine inhibition of platelet 5-hydroxytryptamine transport. J Biol Chem 254:4631-4635
49. Eshleman AJ, Carmolli M, Cumbay M, Martens CR, Neve KA, Janowsky A (1999) Characteristics of drug interactions with recombinant biogenic amine transporters expressed in the same cell type. J Pharmacol Exp Ther 289:877-885
50. Rothman RB, Ayestas MA, Dersch CM, Baumann MH (1999) Aminorex, fenfluramine, and chlorphentermine are serotonin transporter substrates. Implications for primary pulmonary hypertension. Circulation 100:869-875
51. Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (2015) Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs). Neuropharmacology 99:546-553
52. Kalueff AV, Olivier JD, Nonkes LJ, Homberg JR (2010) Conserved role for the serotonin transporter gene in rat and mouse neurobehavioral endophenotypes. Neurosci Biobehav Rev 34:373-386
53. Viggiano D, Ruocco LA, Sadile AG (2003) Dopamine phenotype and behaviour in animal models: in relation to attention deficit hyperactivity disorder. Neurosci Biobehav Rev 27:623-637
54. Xu F, Gainetdinov RR, Wetsel WC, Jones SR, Bohn LM, Miller GW et al (2000) Mice lacking the norepinephrine transporter are supersensitive to psychostimulants. Nat Neurosci 3:465-471
55. Sora I, Hall FS, Andrews AM, Itokawa M, Li XF, Wei HB et al (2001) Molecular mechanisms of cocaine reward: combined dopamine and serotonin transporter knockouts eliminate cocaine place preference. Proc Natl Acad Sci U S A 98:5300-5305
56. O’Neill B, Tilley MR, Han DD, Thirtamara-Rajamani K, Hill ER, Bishop GA et al (2014) Behavior of knock-in mice with a cocaine-insensitive dopamine transporter after virogenetic restoration of cocaine sensitivity in the striatum. Neuropharmacology 79:626-633
57. Brown MT, Bellone C, Mameli M, Labouebe G, Bocklisch C, Balland B et al (2010) Drug-driven AMPA receptor redistribution mimicked by selective dopamine neuron stimulation. PLoS One 5:e15870
58. Hysek CM, Simmler LD, Ineichen M, Grouzmann E, Hoener MC, Brenneisen R et al (2011) The norepinephrine transporter inhibitor reboxetine reduces stimulant effects of MDMA (“ecstasy”) in humans. Clin Pharmacol Ther 90:246-255
59. Hysek CM, Simmler LD, Schillinger N, Meyer N, Schmid Y, Donzelli M et al (2014) Pharmacokinetic and pharmacodynamic effects of methylphenidate and MDMA administered alone or in combination. Int J Neuropsychopharmacol 17:371-381
60. Liechti ME, Baumann C, Gamma A, Vollenweider FX (2000) Acute psychological effects of 3,4-methylenedioxymethamphetamine (MDMA, “Ecstasy”) are attenuated by the serotonin uptake inhibitor citalopram. Neuropsychopharmacology 22:513-521
61. Schmid Y, Hysek CM, Simmler LD, Crockett MJ, Quednow BB, Liechti ME (2014) Differential effects of MDMA and methylphenidate on social cognition. J Psychopharmacol 28:847-856
62. Schmid Y, Rickli A, Schaffner A, Duthaler U, Grouzmann E, Hysek CM et al (2015) Interactions between bupropion and 3,4-methylenedioxymethamphetamine in healthy subjects. J Pharmacol Exp Ther 353:102-111
63. Hysek C, Schmid Y, Rickli A, Simmler L, Donzelli M, Grouzmann E et al (2012) Carvedilol inhibits the cardiostimulant and thermogenic effects of MDMA in humans. Br J Pharmacol 166:2277-2288
64. Hysek CM, Fink AE, Simmler LD, Donzelli M, Grouzmann E, Liechti ME (2013) alpha(1)-Adrenergic receptors contribute to the acute effects of 3,4-methylenedioxymethamphetamine in humans. J Clin Psychopharmacol 33:658-666
65. Hysek CM, Domes G, Liechti ME (2012) MDMA enhances “mind reading” of positive emotions and impairs “mind reading” of negative emotions. Psychopharmacology (Berl) 222:293-302
66. Howell LL, Wilcox KM (2002) Functional imaging and neurochemical correlates of stimulant self-administration in primates. Psychopharmacology (Berl) 163:352-361
67. Derungs A, Schietzel S, Meyer MR, Maurer HH, Krahenbuhl S, Liechti ME (2011) Sympathomimetic toxicity in a case of analytically confirmed recreational use of naphyrone (naphthylpyrovalerone). Clin Toxicol (Phila) 49:691-693
68. Dolder PC, Schmid Y, Haschke M, Rentsch KM, Liechti ME (2015) Pharmacokinetics and concentration-effect relationship of oral LSD in humans. Int J Neuropsychopharmacol 19
69. Eshleman AJ, Wolfrum KM, Hatfield MG, Johnson RA, Murphy KV, Janowsky A (2013) Substituted methcathinones differ in transporter and receptor interactions. Biochem Pharmacol 85:1803-1815
70. Rosenauer R, Luf A, Holy M, Freissmuth M, Schmid R, Sitte HH (2013) A combined approach using transporter-flux assays and mass spectrometry to examine psychostimulant street drugs of unknown content. ACS Chem Neurosci 4:182-190
71. Ross EA, Reisfield GM, Watson MC, Chronister CW, Goldberger BA (2012) Psychoactive “bath salts” intoxication with methylenedioxypyrovalerone. Am J Med 125:854-858
72. Borek HA, Holstege CP (2012) Hyperthermia and multiorgan failure after abuse of “bath salts” containing 3,4-methylenedioxypyrovalerone. Ann Emerg Med 60:103-105
73. Murray BL, Murphy CM, Beuhler MC (2012) Death following recreational use of designer drug “bath salts” containing 3,4-Methylenedioxypyrovalerone (MDPV). J Med Toxicol 8:69-75
74. Simmler LD, Rickli A, Schramm Y, Hoener MC, Liechti ME (2014) Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives. Biochem Pharmacol 88:237-244
75. Bauer CT, Banks ML, Blough BE, Negus SS (2013) Use of intracranial self-stimulation to evaluate abuse-related and abuse-limiting effects of monoamine releasers in rats. Br J Pharmacol 168:850-862
76. Schindler CW, Thorndike EB, Goldberg SR, Lehner KR, Cozzi NV, Brandt SD et al (2015) Reinforcing and neurochemical effects of the “bath salts” constituents 3,4-methylenedioxypyrovalerone (MDPV) and 3,4-methylenedioxy-N-methylcathinone (methylone) in male rats. Psychopharmacology (Berl)
77. Wee S, Anderson KG, Baumann MH, Rothman RB, Blough BE, Woolverton WL (2005) Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs. J Pharmacol Exp Ther 313:848-854
78. Rothman RB, Baumann MH (2006) Balance between dopamine and serotonin release modulates behavioral effects of amphetamine-type drugs. Ann N Y Acad Sci 1074:245-260
79. Watterson LR, Kufahl PR, Nemirovsky NE, Sewalia K, Grabenauer M, Thomas BF et al (2014) Potent rewarding and reinforcing effects of the synthetic cathinone 3,4-methylenedioxypyrovalerone (MDPV). Addict Biol 19:165-174
80. Watterson LR, Olive MF (2014) Synthetic cathinones and their rewarding and reinforcing effects in rodents. Adv Neurosci 2014:209875
81. Sulzer D, Sonders MS, Poulsen NW, Galli A (2005) Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol 75:406-433
82. Rudnick G, Wall SC (1992) The molecular mechanism of “ecstasy” [3,4-methylenedioxy-methamphetamine (MDMA)]: serotonin transporters are targets for MDMA-induced serotonin release. Proc Natl Acad Sci U S A 89:1817-1821
83. Steinkellner T, Freissmuth M, Sitte HH, Montgomery T (2011) The ugly side of amphetamines: short- and long-term toxicity of 3,4-methylenedioxymethamphetamine (MDMA, ‘Ecstasy’), methamphetamine and D-amphetamine. Biol Chem 392:103-115
84. Hill SL, Thomas SH (2011) Clinical toxicology of newer recreational drugs. Clin Toxicol (Phila) 49:705-719
85. Nichols DE (2004) Hallucinogens. Pharmacol Ther 101:131-181
86. Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB (2014) Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function. Psychopharmacology (Berl) 231:875-888
87. Caine SB, Thomsen M, Gabriel KI, Berkowitz JS, Gold LH, Koob GF et al (2007) Lack of self-administration of cocaine in dopamine D1 receptor knock-out mice. J Neurosci 27:13140-13150
88. Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (2016) In vitro characterization of psychoactive substances at rat, mouse, and human trace amine-associated receptor 1. J Pharmacol Exp Ther. doi:10.1124/jpet.115.229765
89. Jing L, Li JX (2015) Trace amine-associated receptor 1: A promising target for the treatment of psychostimulant addiction. Eur J Pharmacol 761:345-352
90. Achat-Mendes C, Lynch LJ, Sullivan KA, Vallender EJ, Miller GM (2012) Augmentation of methamphetamine-induced behaviors in transgenic mice lacking the trace amine-associated receptor 1. Pharmacol Biochem Behav 101:201-207
91. Di Cara B, Maggio R, Aloisi G, Rivet JM, Lundius EG, Yoshitake T et al (2011) Genetic deletion of trace amine 1 receptors reveals their role in auto-inhibiting the actions of ecstasy (MDMA). J Neurosci 31:16928-16940