Cited by 374Parkinson's Disease Mechanisms and TreatmentsRedox biology and oxidative stressGlutathione Transferases and Polymorphisms

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Conjugates of Catecholamines with Cysteine and GSH in Parkinson's Disease: Possible Mechanisms of Formation Involving Reactive Oxygen Species

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Spencer, Jeremy P. E., Jenner, Peter, Daniel, Susan E., Lees, Andrew J., Marsden, David C., Halliwell, Barry·1998·Journal of Neurochemistry

DOI 10.1046/j.1471-4159.1998.71052112.x

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Abstract

Abstract: Oxidation of l ‐3,4‐dihydroxyphenylalanine ( l ‐DOPA) and dopamine (DA) to generate semiquinones/quinones, oxygen radicals, and other reactive oxygen species may play a role in neuronal cell death in Parkinson's disease (PD). In particular, semiquinones/quinones can form conjugates with thiol compounds such as GSH and cysteine. Exposure of l ‐DOPA, DA, and other catecholamines to a system generating O 2 •− radical led to O 2 •− ‐dependent depletion of added GSH (or cysteine), accompanied by the formation of thiol‐DA or ‐DOPA adducts as detected by HPLC. Superoxide could additionally cause destruction of these adducts. Iron or copper ions could also promote conjugate formation between GSH or cysteine and DA and l ‐DOPA, especially if H 2 O 2 was present. We applied HPLC to measure glutathionyl and cysteinyl conjugates of l ‐DOPA, DA, and 3,4‐dihydroxyphenylacetic acid (DOPAC) in postmortem brain samples from PD patients and normal control subjects. Conjugates were detected in most brain areas examined, but levels were highest in the substantia nigra and putamen. In most regions, adduct levels were lower in PD, but there were significant increases in cysteinyl adducts of l ‐DOPA, DA, and DOPAC in PD substantia nigra, suggesting that acceleration of l ‐DOPA/DA oxidation occurs in PD, although we cannot say if this is a primary feature of the disease or if it is related to therapy with l ‐DOPA. In vitro, conjugate formation could be inhibited by the dithiol dihydrolipoate but not by its oxidised form, lipoic acid.

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Halliwell B. and Gutteridge J. M. C. (1989) Free Radicals in Biol- ogy and Medicine, 2nd edit. Clarendon Press, Oxford.

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Enzymes Involved in Processing Glutathione Conjugates
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BackgroundInfluential
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BackgroundResultInfluential
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BackgroundMethod
Oxidative metabolites of 5-S-cysteinyldopamine inhibit the pyruvate dehydrogenase complex
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“However, 5-S-CyS-DA is easily further oxidized by O2 • (Spencer et al., 1998) and under other oxidizing conditions to o-quinone 1 which undergoes a rapid intramolecular cyclization (condensation) to the bicyclic o-quinone imine 2 (Scheme 1).”
BackgroundInfluential

Authors: Spencer, J. P. E., Jenner, P., Daniel, S. E., Lees, A. J., Marsden, D. C., & Halliwell, B.
Affiliations: University of London (GB)
King's College London (GB)
Parkinson's UK (GB)
Corresponding author: Spencer, Jeremy P. E.
ORCID: Spencer, Jeremy P. E.
Jenner, Peter
Daniel, Susan E.
Lees, Andrew J.
Halliwell, Barry
Venue: Journal of Neurochemistry
Publisher: Wiley
Published: 1998-11
Volume: 71
Issue: 5
Pages: 2112-2122
ISSN: 0022-3042 (ISSN-L)
1471-4159
DOI: 10.1046/j.1471-4159.1998.71052112.x
OpenAlex: W2165866163
Cited by: 373
References: 0
Citations by year: 2026: 4 · 2025: 7 · 2024: 6 · 2023: 9 · 2022: 8 · 2021: 7 · 2020: 8 · 2019: 10 · 2018: 2 · 2017: 11 · 2016: 10 · 2015: 14 · 2014: 15 · 2013: 12 · 2012: 19
FWCI: 12.67
Type: journal article
Language: en
Open access: bronze
doi.org
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor, 1473 d)
Locations: Journal of Neurochemistry (publishedVersion)
PubMed (publishedVersion)
UCL Discovery (University College London) (submittedVersion)
Topics: Health Sciences › Medicine › Clinical Neurology › Parkinson's Disease Mechanisms and Treatments
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Glutathione Transferases and Polymorphisms
Keywords: Parkinson's disease, catecholamines, L-DOPA, dopamine, glutathione conjugates, cysteine conjugates, reactive oxygen species, superoxide, semiquinone, quinones, oxidative stress, neuronal cell death, substantia nigra, putamen, alpha-lipoic acid, postmortem brain
MeSH terms: Aged, Aged, 80 and over, Chromatography, High Pressure Liquid, Copper, Cysteine, Dihydroxyphenylalanine, Dopamine, Glutathione, Humans, Iron, Parkinson Disease, Reference Values, Superoxides, 3,4-Dihydroxyphenylacetic Acid, 8,11,14-Eicosatrienoic Acid, Reactive Oxygen Species, Hypoxanthine, Xanthine

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Conjugates of Catecholamines with Cysteine and GSH in Parkinson's Disease: Possible Mechanisms of Formation Involving Reactive Oxygen Species

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