A putative metabolite of serotonin, tryptamine-4,5-dione, is an irreversible inhibitor of tryptophan hydroxylase: Possible relevance to the serotonergic neurotoxicity of methamphetamine

Chemical Research in Toxicology

Volumn 14, Issue 9, 2001, Pages 1184-1192

  Wrona, M Z ^a   Dryhurst, G ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 METHYLENEDIOXYMETHAMPHETAMINE; DRUG METABOLITE; FERROUS ION; METHAMPHETAMINE; NITRIC OXIDE; OXYGENASE INHIBITOR; PEROXYNITRITE; SEROTONIN; SUPEROXIDE; TRYPTAMINE 4,5 DIONE; TRYPTOPHAN HYDROXYLASE; TRYPTOPHAN HYDROXYLASE INHIBITOR; UNCLASSIFIED DRUG;

ANAEROBIC METABOLISM; ANIMAL TISSUE; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; COVALENT BOND; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME INACTIVATION; ENZYME INHIBITION; ENZYME MODIFICATION; MALE; NEUROTOXICITY; NONHUMAN; OXIDATION; RAT; REDUCTION; SEROTONIN METABOLISM;

ANIMALS; BRAIN; CENTRAL NERVOUS SYSTEM STIMULANTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INDOLEQUINONES; MALE; METHAMPHETAMINE; OXIDANTS; OXIDATION-REDUCTION; RATS; RATS, SPRAGUE-DAWLEY; TRYPTAMINES; TRYPTOPHAN HYDROXYLASE;

EID: 0034813505     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx010037c     Document Type: Article

References (66)

1. Neurochemical mechanisms of toxicity
2. Neurotoxicity of amphetamines and their metabolites
3. Rapid ATP loss caused by methamphetamine in the mouse striatum: Relationship between energy impairment and dopaminergic neurotoxicity
4. Effects of 2-deoxy-D-glucose on methamphetamine-induced dopamine and serotonin neurotoxicity
5. Rapid and transient inhibition of mitochondrial function following methamphetamine or 3,4-methylenedioxymethamphetamine administration
6. Hyperthermia depletes adenosine triphosphate and decreases glutamate uptake in rat hippocampal slices
7. Evidence for and mechanism of action of neurotoxicity of amphetamine related compounds
8. Benazmide, an inhibitor of poly(ADP-ribose)polymerase, attenuates methamphetamine-induced dopamine neurotoxicity in the C57B1/6N mouse
9. Causes and consequences of the loss of serotonergic presynapses elicited by the consumption of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy") and its cogeners
10. Protection against methamphetamine-induced neurotoxicity to neostriatal dopamine neurons by adenosine receptor activation
11. Methamphetamine rapidly decreases vesicular dopamine uptake
12. Amphetamine derivatives interact with both plasma membrane and secretory vesicle biogenic amine transporters
13. Carrier-mediated release of neurotransmitters
14. The substituted amphetamines 3,4-methylenedioxymethamphetamine, methamphetamine, p-chloroamphetamine and fenfluramine induce 5-hydroxytryptamine release via a common mechanism blocked by fuoxetine and cocaine
15. Release of serotonin induced by 3,4-methylenedioxymethamphetamine (MDMA) and other substituted amphetamines in cultured fetal raphe neurons: Further evidence for calcium-independent mechanisms of release
16. Multiple methamphetamine injections induce marked increases in extracellular dopamine which correlate with subsequent neurotoxicity
17. Effects of a cold environment or age on methamphetamine-induced dopamine release in the caudate putamen of female rats
18. ATP-regulated neuronal catecholamine uptake: A new mechanism
19. Glutamate becomes neurotoxic when intracellular energy levels are reduced
20. NMDA-dependent superoxide production and neurotoxicity
21. NMDA receptor activation produces concurrent generation of nitric oxide and reactive oxygen species: Implications for cell death
22. Characterization of ionotropic glutamate receptor-mediated nitric oxide production in vivo in rats
23. Roles for excitatory amino acids in methamphetamine-induced nigrostriatal dopaminergic toxicity
24. Effect of MK-801 on the decrease in tryptophan hydroxylase induced by methamphetamine and its methylenedioxy analog
25. Attenuation of methamphetamine-induced neurotoxicity in copper/zinc superoxide dismutase transgenic mice
26. Methamphetamine administration causes overexpression of nNOS in the mouse striatum
27. Effects of 7-nitroindazole, an nNOS inhibitor, on methamphetamine-induced dopaminergic and serotonergic neurotoxicity in mice
28. Methamphetamine generates peroxynitrite and produces dopaminergic neurotoxicity in mice: Protective effects of peroxynitrite decomposition catalyst
29. Depression of rat brain tryptophan hydroxylase activity following the acute administration of methylenedioxymethamphetamine
30. In vitro reactivation of rat cortical tryptophan hydroxylase following in vivo inactivation by methylenedioxymethamphetamine
31. Methamphetamine-induced depression of tryptophan hydroxylase: Recovery following acute treatment
32. Acute inactivation of tryptophan hydroxylase by amphetamine analogs involves the oxidation of sulfhydryl sites
33. Depression of rat brain tryptophan hydroxylase following the acute administration of methylenedioxymethamphetamine
34. Molecular mechanism of the inactivation of tryptophan hydroxylase by nitric oxide: Attack on critical sulfhydryls that spare the enzyme iron center
35. Peroxynitrite inactivates tryptophan hydroxylase via sulfhydryl oxidation. Coincident nitration of enzyme tyrosyl residues has minimal impact on catalytic activity
36. Role of dopamine in the neurotoxic effects of methamphetamine
37. Role of endogenous dopamine in the central serotonergic deficits induced by 3,4-methylenedioxyamphetamine
38. Methamphetamine-induced decrease in tryptophan hydroxylase activity: Role of 5-hydroxytryptaminergic transporters
39. Co-administration of MDMA with drugs that protect against MDMA neurotoxicity produces different effects on body temperature in the rat
40. 3H]dopamine release from superfused rat brain slices
41. The monoamine oxidase-B inhibitor L-deprenyl protects against 3,4-methylenedioxymethamphetamine-induced lipid peroxidation and long-term serotonergic deficits
42. Superoxide radicals mediate the biochemical effects of methylenedioxymethamphetamine (MDMA): Evidence from using CuZn-superoxide dismutase transgenic mice
43. Role of brain nitric oxide in (±)3,4-methylenedioxymethamphetamine (MDMA)-induced neurotoxicity in rats
44. Conjugates of catecholamines with cysteine and GSH in Parkinson's disease. Possible mechanisms of formation involving reactive oxygen species
45. Inhibition of peroxynitrite-mediated oxidation of dopamine by flavonoid and phenolic antioxidants and their structural relationships
46. Dopamine inactivates tryptophan hydroxylase and forms a redox-cycling quinoprotein: Possible endogenous toxin to serotonin neurons
47. Role of hypothermia in the mechanism of protection against serotonergic toxicity. II. Experiments with methamphetamine, p-chloroamphetamine, fen-fluramine, dizocilpine and dextromethorphan
48. Small changes in ambient temperature cause large changes in 3,4-methylenedioxymethamphetamine (MDMA)-induced serotonin neurotoxicity and core body temperature in the rat
49. Co-administration of MDMA with drugs that protect against MDMA neurotoxicity produces different effects on body temperature in the rat
50. Oxidation of serotonin by superoxide radical: Implications to neurodegenerative brain disorders
51. 7-S-Glutathionyl-tryptamine-4,5-dione: A possible aberrant metabolite of serotonin
52. Synthesis and reactivity of the putative neurotoxin tryptamine-4,5-dione
53. Tryptamine-4,5-dione: Properties and reactions with glutathione
54. Activation of tryptophan hydroxylase by adenosine triphosphate, magnesium, and calcium
55. Reaction of protein sulfhydryl groups with Ellman's reagent
56. Fitting curves to data using nonlinear regression: A practical and nonmathematical review
57. Sequence of two mRNAs encoding active rat tryptophan hydroxylase
58. Differential compartmentalization of brain ascorbate and glutathione between neurons and gila
59. Immunocytochemical evidence for methamphetamine-induced serotonergic axon loss in the rat brain
60. Biochemical and histological evidence that methylenedioxymethamphetamine (MDMA) is toxic to neurons in the rat brain
61. Screening of thiol compounds: Depolarization-induced release of glutathione and cysteine from rat brain slices
62. Rapid and specific efflux of glutathione before hepatocyte injury induced by hypoxia
63. Methamphetamine neurotoxicity and striatal glutamate release: Comparison with 3,4-methylenedioxymethamphetamine
64. Rat striatal levels of the antioxidant glutathione are decreased following binge administration of methamphetamine
65. Tryptamine-4,5-dione, a putative endotoxic metabolite of the superoxide-mediated oxidation of serotonin, is a mitochondrial toxin: Possible implications in neurodegenerative brain disorders