Role of cytochrome P450 2E1 in protein nitration and ubiquitin-mediated degradation during acetaminophen toxicity

Abdelmegeed, Mohamed A.; Moon, Kwan-Hoon; Chen, Chi; Gonzalez, Frank J.; Song, Byoung-Joon

doi:10.1016/j.bcp.2009.07.016

Cited by 82Drug-Induced Hepatotoxicity and ProtectionPharmacogenetics and Drug MetabolismRedox biology and oxidative stress

Role of cytochrome P450 2E1 in protein nitration and ubiquitin-mediated degradation during acetaminophen toxicity

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Abdelmegeed, Mohamed A., Moon, Kwan-Hoon, Chen, Chi, Gonzalez, Frank J., Song, Byoung-Joon·2010·Biochemical Pharmacology

DOI 10.1016/j.bcp.2009.07.016PMC PMC2784150

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Abstract

It is well established that following a toxic dose of acetaminophen (APAP), nitrotyrosine protein adducts (3-NT), a hallmark of peroxynitrite production, were colocalized with necrotic hepatic centrilobular regions where cytochrome P450 2E1 (CYP2E1) is highly expressed, suggesting that 3-NT formation may be essential in APAP-mediated toxicity. This study was aimed at investigating the relationship between CYP2E1 and nitration (3-NT formation) followed by ubiquitin-mediated degradation of proteins in wild-type and Cyp2e1-null mice exposed to APAP (200 and 400mg/kg) for 4 and 24h. Markedly increased centrilobular liver necrosis and 3-NT formation were only observed in APAP-exposed wild-type mice in a dose- and time-dependent manner, confirming an important role for CYP2E1 in APAP biotransformation and toxicity. However, the pattern of 3-NT protein adducts, not accompanied by concurrent activation of nitric oxide synthase (NOS), was similar to that of protein ubiquitination. Immunoblot analysis further revealed that immunoprecipitated nitrated proteins were ubiquitinated in APAP-exposed wild-type mice, confirming the fact that nitrated proteins are more susceptible than the native proteins for ubiquitin-dependent degradation, resulting in shorter half-lives. For instance, cytosolic superoxide dismutase (SOD1) levels were clearly decreased and immunoprecipitated SOD1 was nitrated and ubiquitinated, likely leading to its accelerated degradation in APAP-exposed wild-type mice. These data suggest that CYP2E1 appears to play a key role in 3-NT formation, protein degradation, and liver damage, which is independent of NOS, and that decreased levels of many proteins in the wild-type mice (compared with Cyp2e1-null mice) likely contribute to APAP-related toxicity.

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Formation of adduct proteins can prolong protein half-lives and accumulate as aggregated proteins; AA adduct formation and ubiquitin conjugation may compete for common lysine residues, so when lysine residues are occupied by reactive acetaldehyde, lipid aldehydes, AGEs, or AA, adducts persist and may aggregate due to lack of free lysine for ubiquitin conjugation and proteolysis.
“The formation of adduct proteins can prolong protein half-lives and accumulate as aggregated proteins.”
From Advanced glycation end products (AGEs) and other adducts in aging-related diseases and alcohol-mediated tissue injury (2021) · cites this paper as [185]
CYP2E1, one of the main enzymes involved in APAP metabolism, seems to play a critical role in APAP-induced protein nitration and liver injury.
“CYP2E1, one of the main enzymes involved in APAP metabolism, seems to play a critical role in APAP-induced protein nitration and liver injury [93].”
From Mitochondrial dysfunction and tissue injury by alcohol, high fat, nonalcoholic substances and pathological conditions through post-translational protein modifications (2014) · cites this paper as [93]

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Authors: Abdelmegeed, M. A., Moon, K.-H., Chen, C., Gonzalez, F. J., & Song, B.-J.
Affiliations: National Institute on Alcohol Abuse and Alcoholism (US)
National Institutes of Health (US)
Corresponding author: Song, Byoung-Joon
ORCID: Abdelmegeed, Mohamed A.
Chen, Chi
Gonzalez, Frank J.
Song, Byoung-Joon
Venue: Biochemical Pharmacology
Publisher: Elsevier BV
Published: 2010-01
Volume: 79
Issue: 1
Pages: 57-66
ISSN: 0006-2952 (ISSN-L)
DOI: 10.1016/j.bcp.2009.07.016
PMC: PMC2784150
OpenAlex: W2093491167
Cited by: 81
References: 61
Citations by year: 2025: 5 · 2024: 3 · 2023: 2 · 2022: 5 · 2021: 3 · 2020: 4 · 2019: 4 · 2018: 5 · 2017: 4 · 2016: 11 · 2015: 4 · 2014: 4 · 2013: 10 · 2012: 9
FWCI: 5.05
Type: journal article
Language: en
Open access: green
www.ncbi.nlm.nih.gov
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
Locations: Biochemical Pharmacology (publishedVersion)
PubMed (publishedVersion)
Europe PMC (PubMed Central) (acceptedVersion)
PubMed Central (acceptedVersion)
Funders: National Institutes of Health (Z99‐AA999999)
National Institute on Alcohol Abuse and Alcoholism (Z01AA000036)
Topics: Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Drug-Induced Hepatotoxicity and Protection
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
Keywords: CYP2E1, acetaminophen toxicity, protein nitration, nitrotyrosine, ubiquitin-mediated proteolysis, superoxide dismutase 1, peroxynitrite, liver necrosis, nitric oxide synthase, drug metabolism
MeSH terms: Acetaminophen, Animals, Female, Male, Nitrates, Proteins, Mice, Knockout, Cytochrome P-450 CYP2E1, Ubiquitin, Mice

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Role of cytochrome P450 2E1 in protein nitration and ubiquitin-mediated degradation during acetaminophen toxicity

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