Cited by 1,126melanin and skin pigmentationParkinson's Disease Mechanisms and TreatmentsBioactive Compounds and Antitumor Agents

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Oxidative Pathways for Catecholamines in the Genesis of Neuromelanin and Cytotoxic Quinones

GRAHAM, DOYLE G.·1978·Molecular Pharmacology

DOI 10.1016/s0026-895x(25)13535-9

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Concepts of Scientific Integrative Medicine Applied to the Physiology and Pathophysiology of Catecholamine Systems
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“…sequestration of catecholamines that leak passively from the vesicles into the cytosol would result also in buildup of catecholamines in the cytosol, where they are “autotoxic” because of spontaneous oxidation to quinones (148) and chromes (287) and because of enzymatic oxidation to aldehydes (31).”
Review on the interactions between dopamine metabolites and α-Synuclein in causing Parkinson's disease
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1-(Pyridin-2-ylmethyl)-2-(3-(1-(pyridin-2-ylmethyl)benzimidazol-2-yl) propyl) benzimidazole and its copper(II) complex as a new fluorescent sensor for dopamine (4-(2-aminoethyl)benzene-1,2-diol)
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l-DOPA-induced 6-hydroxydopamine production in the striata of rodents is sensitive to the degree of denervation
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Methamphetamine mimics the neurochemical profile of aging in rats and impairs recognition memory
Melo, P., Magalhães, A., Alves, C. J., Ferreira, M. A., de Sousa, L., Summavielle, T., & Moradas‐Ferreira, P. (2012) · NeuroToxicology · doi:10.1016/j.neuro.2012.03.002 · Cited by 29
“Oxidation of DA produces H2O2 via monoamino oxidase A (MAO-A) (Capela et al., 2009 and Graham, 1978) leading to a decrease number of DATs (Fleckenstein et al., 1997 and Metzger et al., 2000).”
Background
Dopamine Selectively Sensitizes Dopaminergic Neurons to Rotenone-Induced Apoptosis
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“What is then the cause of DA-induced toxicity? That DA neurons may already be at an increased state of oxidative stress due to autooxidation of cytoplasmic DA into DA-quinones and enzymatic metabolism of DA yielding H2O2 has been recognized for at least three decades [5].”
Background
Extracellular norepinephrine reduces neuronal uptake of norepinephrine by oxidative stress in PC12 cells.
Mao, W.-K., Qin, F.-Z., Iwai, C., Vulapalli, R., Keng, P., & Liang, C.-S. (2004) · American Journal of Physiology. Heart and Circulatory Physiology · doi:10.1152/ajpheart.01168.2003 · Cited by 36
“However, it is known that free radicals are formed after autooxidation of NE to NE-orthoquinone and hydroquinone (19, 42), which can be enhanced by transition ions such as Cu(2) and Fe(2) .”
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Dopamine Prevents Nitration of Tyrosine Hydroxylase by Peroxynitrite and Nitrogen Dioxide
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Differential sensitivity to hydrogen peroxide of dopaminergic and noradrenergic neurotransmission in rat brain slices
Langeveld, C. H., Schepens, E., Stoof, J. C., Bast, A., & Drukarch, B. (1995) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(95)00014-o · Cited by 29
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“If not secreted, dopamine could be auto-oxidized or deaminated by monoamine oxidase (MAO), during which several cytotoxic molecules, including dopamine– quinone species (SQ), OH, and H2O2 are generated (Graham, 1978; Maker et al., 1981).”
Background
The separation and quantification of aminochromes using high-pressure liquid chromatography with electrochemical detection
Ochs, S. D., Westfall, T. C., & Macarthur, H. (2004) · Journal of Neuroscience Methods · doi:10.1016/j.jneumeth.2004.08.010 · Cited by 28
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Cytotoxicity of dopamine-derived tetrahydroisoquinolines on melanoma cells
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Characterization of reduced and oxidized dopamine and 3,4-dihydrophenylacetic acid, on brain mitochondrial electron transport chain activities
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“In the current study, DA was monitored at 480 nm [8] and DOPAC at 400 nm [24] and standard curves made from tyrosinase-mediated fully oxidized DA and DOPAC solutions were used to quantify the desired quinone concentration at the time of exposure (Insets to Figs.”
Cytoprotective role of taurine in a renal epithelial cell culture model
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Absence of neurotoxicity of chronic L-DOPA in 6-hydroxydopaminelesioned rats
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Hypochlorite converts cysteinyl-dopamine into a cytotoxic product: A possible factor in Parkinson's Disease
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“Auto- and enzymatic oxidation of L-DOPA can lead to the production of various reactive oxygen species such as superoxide or hydrogen peroxide and to the production of semiquinones and quinones (Graham, 1978; Bindoli et al., 1992).”
The effect of vitamin E addition to acute neuroleptic treatment on the emergence of extrapyramidal side effects in schizophrenic patients: An open label study
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“Furthermore, ethanol-induced overactivity of catecholaminergic neurons may enhance the auto-oxidation of catecholamines, producing oxygen free radicals and semiquinones, which may eventually lead to neuronal death (Graham, 1978).”
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Methylparaben protects 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y cells and improved behavioral impairments in mouse model of Parkinson's disease
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“…with molecular O2) to form several potentially cytotoxic species, including DA-semiquinone, DA-hydroquinone, DA-o-quinone, DA-p-quinone, and dopaminochrome (Bindoli et al., 1999; Graham, 1978; Segura-Aguilar, 1999; Senoh et al., 1959a; Senoh and Witkop, 1959a, 1959b; Sulzer and Zecca, 1999).”
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Neuromelanin in the Human Brain: A Review and Atlas of Pigmented Cells in the Substantia Nigra
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Reduction reactivity of catecholamines and their ability to promote a Fenton reaction
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Dopamine Metabolism and Reactive Oxygen Species Production
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“The toxicity induced by l-DOPA treatment is similar to that induced by oxidation of DA: l-DOPA can also auto-oxidize and form reactive quinones that will contribute to an increase in oxidative stress [58].”
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Behavioral effects of intra-nigral microinjections of manganese chloride: Interaction with nitric oxide
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The role of metals in the enzymatic and nonenzymatic oxidation of epinephrine
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Modulation of Chemokine Production in Lung Microvascular Endothelial Cells by Dopamine Is Mediated via an Oxidative Mechanism
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Production of melanin pigments by cytochrome c/H2O2 system
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Quinoprotein Adducts Accumulate in the Substantia Nigra of Aged Rats and Correlate with Dopamine-Induced Toxicity in SH-SY5Y Cells
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“Notably, the DAQ-cysteinyl adduct was formed when DAQ was incubated with glutathione [10], tyrosine hydroxylase [29, 30], and several mitochondrial proteins [32, 33], suggesting a potential contribution of quinoprotein adduct formation to these DAQ caused alterations.”
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Role of Protein Damage Inflicted by Dopamine Metabolites in Parkinson’s Disease: Evidence, Tools, and Outlook
Hurben, A. K., & Tretyakova, N. Y. (2022) · Chemical Research in Toxicology · doi:10.1021/acs.chemrestox.2c00193 · Cited by 25
Involvement of antioxidant enzymes in Parkinson’s disease
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Computational analysis of determinants of dopamine (DA) dysfunction in DA nerve terminals
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Correlation of axon size and myelin occupancy in rats prenatally exposed to methamphetamine
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“Dopamine reacts with molecular oxygen to form reactive oxygen species, such as superoxide, hydroxyl free radicals and hydrogen peroxide (Graham, 1978).”
Glial loss of the metallo β-lactamase domain containing protein, SWIP-10, induces age- and glutamate-signaling dependent, dopamine neuron degeneration
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Nonsteroidal anti-inflammatory drugs in Parkinson’s disease: possible involvement of quinone formation
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“In neuro-pigmentation, neuromelanin is formed by nonenzymatic autoxidation of cytoplasmic DA to DA-quinone that subsequently cyclizes and oxidatively polymerizes [20,21].”
Background
Exposure to Far Infrared Ray Protects Methamphetamine-Induced Behavioral Sensitization in Glutathione Peroxidase-1 Knockout Mice via Attenuating Mitochondrial Burdens and Dopamine D1 Receptor Activation
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Aldose reductase deficiency leads to oxidative stress-induced dopaminergic neuronal loss and autophagic abnormality in an animal model of Parkinson's disease
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“Furthermore, the reduction in GSH levels could be related to high GSH consumption as well as binding of levodopa derived quinones to the remaining GSH molecules [53].”
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Catecholamine Analogs as Potential Antitumor Agents
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Catecholamine melanins. Structural changes induced by copper ions
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Possible actions of cannabidiol in obsessive-compulsive disorder by targeting the WNT/β-catenin pathway
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Methamphetamine causes depletion of glutathione and an increase in oxidized glutathione in the rat striatum and prefrontal cortex
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“DA reacts with molecular oxygen to form quinones and semiquinones (Graham, 1978).”
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Oxidative metabolism of dopamine: A colour reaction from human midbrain analysed by mass spectrometry
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“These experiments, and those of others [23,24], have demonstrated that the process of melanogenesis of catecholamines can be closely monitored in its early stages by the formation of an absorbance peak at 480 nm.”
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Role of nitroso radicals as drug targets in circulatory shock
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Authors: GRAHAM, D. G.
Affiliations: Duke Medical Center (US)
Corresponding author: GRAHAM, DOYLE G.
Venue: Molecular Pharmacology
Publisher: Elsevier BV
Published: 1978-07
Volume: 14
Issue: 4
Pages: 633-643
ISSN: 0026-895X (ISSN-L)
DOI: 10.1016/s0026-895x(25)13535-9
OpenAlex: W2211987820
Cited by: 1,126
References: 0
Citations by year: 2026: 11 · 2025: 12 · 2024: 6 · 2023: 11 · 2022: 13 · 2021: 20 · 2020: 23 · 2019: 26 · 2018: 29 · 2017: 30 · 2016: 26 · 2015: 29 · 2014: 26 · 2013: 26 · 2012: 49
FWCI: 1.86
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
Locations: Molecular Pharmacology (publishedVersion)
PubMed (publishedVersion)
PubMed
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Cell Biology › melanin and skin pigmentation
Health Sciences › Medicine › Clinical Neurology › Parkinson's Disease Mechanisms and Treatments
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Bioactive Compounds and Antitumor Agents
Keywords: catecholamines, autoxidation, periodate oxidation, 6-hydroxydopamine, dopamine, norepinephrine, epinephrine, aminochrome, adrenochrome, o-quinones, p-quinones, cyclization, tautomerism, neuromelanin
MeSH terms: Catecholamines, Dopamine, Epinephrine, Hydroxydopamines, Melanins, Norepinephrine, Oxidation-Reduction, Quinones, Monophenol Monooxygenase

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Oxidative Pathways for Catecholamines in the Genesis of Neuromelanin and Cytotoxic Quinones

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