tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand

Gharavi, Negar; El-Kadi, Ayman O.S.

doi:10.1124/dmd.104.002253

Cited by 87Toxic Organic Pollutants ImpactPharmacogenetics and Drug MetabolismCarcinogens and Genotoxicity Assessment

tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand

Gharavi, Negar, El-Kadi, Ayman O.S.·2005·Drug Metabolism and Disposition

DOI 10.1124/dmd.104.002253

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Abstract

In contrast to the beneficial effects of tert-butylhydroquinone (tBHQ) as a food antioxidant, a number of studies have shown that chronic exposure to tBHQ may induce carcinogenicity. Therefore, we examined the ability of tBHQ to induce the cytochrome P450 1a1 (Cyp1a1), an enzyme known to play an important role in the chemical activation of xenobiotics to carcinogenic derivatives. A significant concentration-dependent increase in Cyp1a1 mRNA, protein, and activity occurred after treatment of murine hepatoma Hepa 1c1c7 cells with tBHQ. The increase in mRNA was apparent 3 h after treatment. The RNA polymerase inhibitor, actinomycin D, completely blocked the Cyp1a1 induction by tBHQ, indicating a requirement of de novo RNA synthesis through transcriptional activation. The protein synthesis inhibitor cycloheximide superinduced the tBHQ-mediated induction of Cyp1a1 mRNA and completely prevented the increase in Cyp1a1 activity, indicating that the induction of enzyme activity by tBHQ is dependent on de novo protein synthesis. In addition, the aryl hydrocarbon receptor (AHR) antagonist, resveratrol, inhibited the increase in Cyp1a1 activity by tBHQ. Gel electrophoretic mobility shift assays showed that tBHQ causes activation or transformation of the AHR in nuclear extracts, indicating that AHR-dependent mechanisms contributed to the Cyp1a1 induction. Similar to murine Hepa 1c1c7 cells, tBHQ caused a concentration-dependent increase in CYP1A1 at the mRNA and activity levels in human HepG2 cells. This is the first demonstration that the phenolic antioxidant, tBHQ, can directly induce Cyp1a1 gene expression in an AHR-dependent manner and may represent a novel mechanism by which tBHQ promotes carcinogenicity.

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tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand. Drug Metab Dispos 2005; 33(3
Gharavi, N., & El‐Kadi, A. O. S. (2016)
Self-citation
REGULATION OF CYP1A1 GENE EXPRESSION BY THE ANTIOXIDANT TERT-BUTYLHYDROQUINONE
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Chemoprotective and Carcinogenic Effects of tert-Butylhydroquinone and Its Metabolites
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Genotoxic polycyclic aromatic hydrocarbon ortho-quinones generated by aldo-keto reductases induce CYP1A1 via nuclear translocation of the aryl hydrocarbon receptor.
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2‐(4′‐Chlorophenyl)benzothiazole is a potent inducer of cytochrome P450IA1 in a human and a mouse cell line
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Authors: Gharavi, N., & El-Kadi, A. O. S.
Affiliations: University of Alberta (CA)
Venue: Drug Metabolism and Disposition
Publisher: Elsevier BV
Published: 2005-03
Volume: 33
Issue: 3
Pages: 365-372
ISSN: 0090-9556 (ISSN-L)
DOI: 10.1124/dmd.104.002253
OpenAlex: W2136785877
Cited by: 87
References: 40
Citations by year: 2026: 1 · 2025: 3 · 2024: 1 · 2023: 3 · 2022: 3 · 2021: 5 · 2020: 3 · 2019: 4 · 2018: 4 · 2017: 10 · 2016: 6 · 2015: 3 · 2014: 6 · 2013: 4 · 2012: 6
FWCI: 2.36
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: Drug Metabolism and Disposition (publishedVersion)
PubMed (publishedVersion)
Topics: Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Toxic Organic Pollutants Impact
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Carcinogens and Genotoxicity Assessment
Keywords: tert-butylhydroquinone, aryl hydrocarbon receptor, CYP1A1 induction, gene expression regulation, hepatoma cells, Hepa1c1c7 cells, HepG2 cells, resveratrol, carcinogenicity, phenolic antioxidants, transcriptional activation, protein synthesis dependence, xenobiotic metabolism
MeSH terms: Animals, Antioxidants, Cell Survival, Enzyme Induction, Hydroquinones, Ligands, RNA, Messenger, Gene Expression Regulation, Enzymologic, Receptors, Aryl Hydrocarbon, Cytochrome P-450 CYP1A1, Cell Line, Tumor, Mice

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tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand

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