Potential oxidative pathways of brain catecholamines
Abstract
The possibility that catecholamines can be oxidized via aberrant pathways in vivo is open to question, but in vitro oxidation via aerobic manipulations is established. Assuming oxidation does occur, we have examined quantitatively the fast chemical reactions of the initial oxidation products, the o-quinones. The nature and rates of these reactions were studies under the conditions simulating closely those which presumably exist in mammalian brain. The results are in close accord with existing literature and especially support oxidation pathways recently reported in [3H]-norepinephrine binding to particulate cell fractions.
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When iron is present in the cytosol, dopamine can be oxidized into dopamine quinone (DAQ), which is highly reactive and toxic.
“When iron is present in the cytosol (as may occur more frequently with ageing)265,266, dopamine can be oxidized into dopamine quinone (DAQ), which is highly reactive and toxic267,268.”
From Rhythms of life: circadian disruption and brain disorders across the lifespan (2019) · cites this paper as [268]
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“The rate constant of the nucleophilic addition of GSH to DQ has been described to be three orders of magnitude greater than the cyclization reaction, with a rate constant of ~200 s [24].”
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Oxidation of DNA, proteins and lipids by DOPA, protein-bound DOPA, and related catechol(amine)s
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Liu, L., Du, J., Li, S., et al. (2012) · Biosensors and Bioelectronics · doi:10.1016/j.bios.2012.09.061 · Cited by 78 · see citing works
“In addition, the oxidation products of DA can react with ascorbate acid present in sample and regenerate DA that becomes available again for oxidation, which severely limits the accuracy of detection (Ali et al., 2007a; Tse et al., 1976).”
BackgroundNeuromelanin of the Human Substantia Nigra: A Mixed‐Type Melanin
Odh, G., Carstam, R., Paulson, J., Wittbjer, A., Rosengren, E., & Rorsman, H. (1994) · Journal of Neurochemistry · doi:10.1046/j.1471-4159.1994.62052030.x · Cited by 77 · see citing works
Chemical and biochemical control of skin pigmentation with special emphasis on mixed melanogenesis
Wakamatsu, K., Zippin, J. H., & Ito, S. (2021) · Pigment Cell & Melanoma Research · doi:10.1111/pcmr.12970 · Cited by 77 · see citing works
Dopamine-Induced Behavioral Changes and Oxidative Stress in Methamphetamine-Induced Neurotoxicity
Kita, T., Miyazaki, I., Asanuma, M., Takeshima, M., & Wagner, G. C. (2009) · International review of neurobiology · doi:10.1016/s0074-7742(09)88003-3 · Cited by 77 · see citing works
“Dopamine quinones are also generated in the enzymatic oxidation of dopamine by prostaglandin H synthase (cyclooxygenase: COX), lipoxygenase, tyrosinase, and xanthine oxidase (Foppoli, et al., 1997; Graham, 1978; Hastings, 1995; Korytowski et al., 1987; Rosei et al., 1994; Tse et al., 1976).”
BackgroundAsanuma, M., Miyazaki, I., Diaz-Corrales, F. J. J., & Ogawa, N. (2004) · PubMed · doi:10.18926/amo/32105 · Cited by 76 · see citing works
Dopamine voltammetry at overoxidised polyindole electrodes
Ghita, M., & Arrigan, D. W. M. (2004) · Electrochimica Acta · doi:10.1016/j.electacta.2004.05.030 · Cited by 75 · see citing works
Urate in Parkinson’s Disease: More Than a Biomarker?
Chen, X. M., Wu, G.-H., & Schwarzschild, M. A. (2012) · Current Neurology and Neuroscience Reports · doi:10.1007/s11910-012-0282-7 · Cited by 74 · see citing works
- Authors
- Tse, D. C. S., McCreery, R. L., & Adams, R. N.
- ORCID
- McCreery, Richard L.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1976-01
- Volume
- 19
- Issue
- 1
- Pages
- 37-40
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2008158988
- Cited by
- 415
- References
- 0
- Citations by year
- 2026: 2 · 2025: 6 · 2024: 9 · 2023: 4 · 2022: 20 · 2021: 15 · 2020: 6 · 2019: 16 · 2018: 15 · 2017: 11 · 2016: 20 · 2015: 14 · 2014: 10 · 2013: 10 · 2012: 10
- FWCI
- 0.93
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Medicinal Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Physical Sciences › Chemistry › Organic Chemistry › Oxidative Organic Chemistry Reactions
- Keywords
- catecholamines, oxidative metabolism, o-quinones, norepinephrine, brain, in vitro oxidation, reaction kinetics
- MeSH terms
- Ascorbic Acid, Brain, Catecholamines, Cyclization, Dopamine, Electrochemistry, Glutathione, Kinetics, Oxidation-Reduction, Quinones, In Vitro Techniques
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