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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“In part due to dopamine metabolism by endogenous enzymes such as monoamine oxidases (MAO) or by autooxidation that can yield H2O2 and dopamine-quinones, the neurons in the SN are especially vulnerable to oxidative stress (57, 58, 129, 133).”
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“…can directly injure nigrostriatal dopaminergic neurons via oxidization of dopamine, creating reactive oxygen species (ROS), and dopamine quinones that damage lipid membranes, proteins, DNA, and mitochondria (Berman and Hastings, 1999; Graham, 1978; Miyazaki and Asanuma, 2009; Stokes et al., 1999).”
Background
Human Class Mu Glutathione Transferases, in Particular Isoenzyme M2-2, Catalyze Detoxication of the Dopamine Metabolite Aminochrome
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“Also, like the neurotoxin 6-hydroxydopamine, dopamine and related o-catechols are unstable molecules that can oxidize in the presence of transition metals to form reactive oxygen species (ROS) and quinones that may modify proteins, lipids, and nucleic acids (41, 42).”
Background
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“Chemically, DA contains a catechol structure that can spontaneously oxidize in vitro or via an enzyme-catalyzed reaction in vivo to form reactive oxygen species (ROS) and quinones (Graham, 1978).”
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“The generation of o-quinones from these molecules during metabolism produces reactive species capable of arylating cellular nucleophiles (Graham, 1978; Graham et al., 1978; Khan et al., 2001) Thus, metabolic intermediates in the dopaminergic pathway are capable of both arylation and inducing oxidative stress (Scheme 2…”
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“…underlying Parkinson’s disease may involve the oxidation of dopamine to the o-quinone aminochrome (Foppoli et al., 1997; Galzigna et al., 2000; Graham, 1978; Hastings, 1995; Hawley et al., 1967; Paris et al., 2001; Rabinovic et al., 2000; SeguraAguilar, 1996; Segura-Aguilar and Lind, 1989;…”
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“NM, a product of catecholamine degradation, is of particular interest because it 1) possesses harmful properties (Graham, 1978; Jellinger, 1999); 2) is concentrated within nigrostriatal neurons during aging (Zecca et al. 2002); and 3) appears to be capable of enhancing MPTP toxicity (D’Amato et…”
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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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