A notable exception is acetaminophen hepatotoxicity, which is associated with the formation of a well-characterized and highly reactive intermediate metabolite, N-acetyl-p-benzoquinone imine. (nih.gov)
The key mechanism in APAP induced hepatotoxicity is the CYP450 catalyzed formation of the reactive metabolite, N-acetyl-p-benzoquinone imine which depletes hepatic glutathione and accumulates to cause excessive cellular oxidative stress. (tufts.edu)
For instance, N -acetyl- p -benzoquinone imine (NAPQI) protein adducts trigger mitochondrial oxidative/nitrosative stress during hepatocyte necrosis , danger-associated molecular patterns (DAMPs) are released to elicit sterile inflammation , and certain growth factors contribute to liver regeneration. (zju.edu.cn)
For instance, the molar dose fraction of APAP converted to the oxidative metabolite N-acetyl-p-benzoquinone imine increases during pregnancy. (oullins-patriote.com)
Paracetamol overdose is associated with major side effects such as liver damage through its metabolite N-acetyl-p-benzoquinone Imine. (ac.ke)
Unfortunately, when taken excessively, this drug can cause acute liver failure, through the formation of its reactive metabolite, N-acetyl p-benzoquinone imine (NAPQI). (hepato-neuro.ca)
One in particular, N -acetyl- p -benzoquinone imine, is usually broken down in the liver by the antioxidant glutathione, which conjugates with the compound and renders it safe. (rsc.org)
Only about 5% is oxidised to the highly reactive toxic metabolite, N-acetyl-p-benzoquinone imine (NAPQI), which can be detoxified by hepatic glutathione(GSH). (paganz.org)
Excessive accumulation of reactive metabolite, N-acetyl-p-benzoquinone-imine (NAPQI) increases oxidative stress in tissues, leading to centrilobular necrosis after exceeding the glutathione (GSH) threshold. (upm.edu.my)
An FMN-dependent monooxygenase, encoded by the sadA gene, was shown to catalyze ipso-substitution of sulfonamides, initiating their fragmentation to 4-benzoquinone-imine, sulfite and the moiety previously attached to the sulfo group. (kit.edu)
While 4-benzoquinone-imine serves as the source of carbon and energy, the mostly heterocyclic moiety was shown to remain a dead-end metabolite in culture supernatants. (kit.edu)
Jessica Monson will speak on 'N-Acetyl-p-benzoquinone Imine, the Toxic Metabolite of Acetaminophen, is a Topoisomerase II Poison,' and Steven Enke will speak on 'Single and Mixed Oxide-Supported Nickel Catalysts for the Catalytic Partial Oxidation Reforming of Gasoline' at this tomorrow's Chemistry Seminar. (stthomas.edu)
Because acetaminophen is hepatotoxic (liver toxic), and in cases of acetaminophen overdose (which is potentially fatal), NAC is the treatment of choice to minimize the liver damage caused by the acetaminophen metabolite N-acetyl-p-benzoquinone imine. (naturescomplement.com)
When there is an overdosage, the conjugation in the liver becomes saturated, and excess APAP is oxidatively metabolized by the cytochrome P enzymes to a reactive metabolite, N-acetyl-p-benzoquinone-imine (NAPOI). (medicalisland.net)
Acetaminophen's reactive metabolite N-acetyl-p-benzoquinone imine (NAPQI) can cause a potentially fatal, hepatic necrosis through the process of lipid peroxidation if acetaminophen is overdosed (more than 4g daily). (marcelcastellano.com)
Toxicity of acetaminophen may cause autism by overloading the defective sulfation pathway catalyzed by phenolsulfotransferase, which is deficient in autism, leading to overproduction of the toxic metabolite N-acetyl-p-benzoquinone imine (NAPQI). (drkeithsown.com)
Benzene metabolites5
Certain benzene metabolites, including benzoquinone (BQ), are genotoxic and mutagenic. (rti.org)
Relationship between the oxidation potential of benzene metabolites and their inhibitory effect on DNA synthesis in L5178YS cells. (aspetjournals.org)
In vitro effects of benzene metabolites on mouse bone marrow stromal cells. (cdc.gov)
The authors conclude that benzene metabolites are toxic to mouse bone marrow stromal cells in-vitro. (cdc.gov)
There was a really interesting study back in 2007, where researchers found that benzene metabolites including catachol, hydroquinone, 1,2,4-benzenetriol and 1,4-benzoquinone triggered cytokine release from red blood cells. (annierubin.com)
Acetaminophen1
To investigate the effects of acetaminophen on circulating bile acid profiles, metabolites were extracted from human serum samples from patients with APAP-related acute liver failure and healthy controls. (hepato-neuro.ca)
Reactive2
This Review highlights new developments regarding the potential role of reactive metabolites, mitochondrial toxicity, host immune-response pathways and biliary transporters in the etiopathogenesis of DILI. (nih.gov)
Characterization of the S-(2,5-dihydroxyphenyl)cysteine adduct provides evidence that p-benzoquinone is formed as a reactive metabolite of benzene. (aacrjournals.org)
Glutathione3
glutathione stores in the liver detoxify this metabolite. (msdmanuals.com)
In an overdose, however, there's simply not enough glutathione to cope, and the metabolite is instead free to interact with liver proteins, causing extensive damage. (rsc.org)
Cells were exposed to benzene, phenol, catechol, hydroquinone, p-benzoquinone, or 1,2,4-benzenetriol over the range of 1.0 X 10(-7) to 1.0 X 10(-2) M for 30 min, and the rate of DNA synthesis was measured at various times after chemical washout. (aspetjournals.org)
Benzoquinone was the most potent inhibitor of DNA synthesis, followed by hydroquinone, benzenetriol, catechol, and phenol with ED50 values of 5 X 10(-6), 1 X 10(-5), 1.8 X 10(-4), 2.5 X 10(-4), and 8.0 X 10(-4), respectively. (aspetjournals.org)
Bone marrow cell suspensions were prepared from male B6C3F1-mice and cultured with hydroquinone (123319), benzoquinone (106514), catechol (120809), phenol (108952), and 1,2,4-benzenetriol (533733) at concentrations from 0.0000015 to formed in the presence of these metabolites was determined and compared with values from untreated stromal cell cultures. (cdc.gov)
Hydroquinone and benzoquinone had dose related effects. (cdc.gov)
Hydroquinone completely inhibited cell growth at concentrations above 0.0000125mole, and benzoquinone had the same effect at a concentration of 0.00005mol. (cdc.gov)
In the simultaneous culture system, stromal cell exposure to hydroquinone and benzoquinone produced dose dependent decreases in granulocyte monocyte colonies. (cdc.gov)
Hydroquinone, and its mercapturic acid pathway metabolites, cause renal proximal tubular cell necrosis and nephrocarcinogenicity in rats. (elsevierpure.com)
Biological effects resulting from the Cu/Zn-superoxide dismutase-accelerated oxidation of the benzene metabolite 1,4-hydroquinone. (shengsci.com)
Cu/Zn-superoxide dismutase (SOD)-accelerated oxidation of the benzene metabolite 1,4-hydroquinone (HQ) results in the enhanced formation of semiquinone anion radicals, electrophilic 1,4-benzoquinone (BQ), and H202. (shengsci.com)
Electrophilic2
Common among these 10 interactions of organic compounds, their power to detect excess cancer agents is the electrophilic nature of or their metabolites, with DNA and R 1 risk at particular sites. (who.int)
The adverse effects of HQ and its thioether metabolites are in part a consequence of their oxidation to the corresponding electrophilic 1,4-benzoquinones (BQ). (elsevierpure.com)
Oxidation4
The ease of oxidation of these metabolites correlated with their ED50 values for inhibition of DNA synthesis (r = 0.997). (aspetjournals.org)
This suggests that oxidation of phenol or one of its metabolites may be necessary for production of the species involved in inhibition of DNA synthesis. (aspetjournals.org)
The structures of several previously reported metabolites were confirmed, the identities of four new metabolites were determined, pathways of oxidation were investigated, and quantitative data were obtained for several of the products. (aspetjournals.org)
Additional metabolites were produced by oxidation of BHT-BzOH to the corresponding benzaldehyde and benzoic acid derivatives. (aspetjournals.org)
Pathways2
Labeling of Trypanosoma brucei cell cultures with 50% uniformly 13C-labeled glucose demonstrated incorporation of glucose-derived carbon into 187 of 588 putatively identified metabolites in diverse pathways including carbohydrate, nucleotide, lipid, and amino acid metabolism. (acs.org)
Labeling patterns confirmed the metabolic pathways responsible for the biosynthesis of many detected metabolites, and labeling was detected in unexpected metabolites, including two higher sugar phosphates annotated as octulose phosphate and nonulose phosphate. (acs.org)
Toxicity1
The direct toxicity of benzene could be distinguished from that of its metabolites since bioactivation of benzene in L5178YS cells was not observed. (aspetjournals.org)
Polyphenols1
It is a product of microbial transformation of dietary polyphenols and endogenous metabolites such as dopamine, phenylalanine, tyrosine, and tryptophan. (healthmatters.io)
Tyrosine1
Tyrosine and p -benzoquinone were the dominant metabolites in all of the secretions, accounting for approximately 11.29% of emissions, with the portion in the solid phase being generally higher than that in the liquid phase. (frontiersin.org)
Secondary2
Unfortunately, somewhat less effort has been devoted to the characterization or understanding of non-essential or secondary metabolism and non-essential metabolites, partly due to their much higher number, and greater structural complexity, compared to primary metabolites. (biomedcentral.com)
The natural quinone, hydroxydietrichequinone (3-heptadec-8-enyl-2-hydroxy-5-methoxy-[1,4]benzoquinone) is a secondary metabolite of Cyperus javanicus. (lookformedical.com)
Precursor1
The combination of high-resolution LC-MS-based untargeted metabolomics with stable isotope tracing provides a global overview of the cellular fate of precursor metabolites. (acs.org)
Pathway1
Furthermore BioTransformer was able to reproduce 100% of the transformations and metabolites predicted by the EAWAG pathway prediction system. (biomedcentral.com)
Adducts1
The present study was aimed at the characterization of the major adducts formed by reaction of the metabolites of [14C]benzene with rat hemoglobin in vivo. (aacrjournals.org)
Cytochrome1
We now report that BQ and 2-(7V-acetylcystein-S-yl)benzoquinone (NAC-BQ) preferentially bind to solvent-exposed lysine-rich regions within cytochrome c. (elsevierpure.com)
Vitro1
The effects of benzene (71432) metabolites on bone marrow stromal cells were investigated in-vitro. (cdc.gov)
Bone1
Stromal cells exposed to metabolites at these same concentrations were also cultured simultaneously with fresh bone marrow cells in agar to measure the effect on the ability of stromal cells to support growth of granulocyte monocyte colony forming cells. (cdc.gov)
Quantification2
This methodology enables detection of putative metabolites from biological samples and simultaneous quantification of the pattern and extent of isotope labeling. (acs.org)
strain BR1 Sulfonamide removal rate of the sludges will be determined by quantification of sulfonamides and dead-end metabolites in influent and effluent of the wastewater treatment plants. (kit.edu)
Amino1
Over the past 100 years, considerable effort has gone into determining the precise molecular details of primary metabolism-i.e. the metabolic processes associated with the production and breakdown of essential metabolites (e.g. lipids, amino acids, and steroids) [ 1 ]. (biomedcentral.com)
Biological1
In the proposed project, we will evaluate whether the identified dead-end metabolites can also be linked to biological sulfonamide degradation. (kit.edu)
Production1
N-acetylcysteine blocks the production of toxic metabolites and hence acts as an antidote. (medicalisland.net)
Previously1
Using mass spectrometry data obtained from a rat experimental study with epicatechin supplementation, BioTransformer was also able to correctly identify 39 previously reported epicatechin metabolites via its metabolism identification tool, and suggest 28 potential metabolites, 17 of which matched nine monoisotopic masses for which no evidence of a previous report could be found. (biomedcentral.com)
Activity3
The liquid phase shared a number of metabolites with the solid phase, but the emission types and amounts were significantly different in the two phases, resulting in differences in external immunological activity. (frontiersin.org)
This hypothesis was further demonstrated by the antimicrobial activity of p -benzoquinone. (frontiersin.org)
4-hydroxybenzoic acid is the common metabolite of all parabens, structurally related benzoic acid (without the OH group) and has potential endocrine activity. (healthmatters.io)
Principal1
Quantitative data demonstrate that BHT-BzOH is the principal metabolite in rat liver and lung microsomes. (aspetjournals.org)
Effects1
The effects of benzene and its metabolites on the rate of DNA synthesis were measured in the mouse lymphoma cell line, L5178YS. (aspetjournals.org)
Mouse1
Mouse lung, however, produced more quinone relative to other metabolites than mouse liver. (aspetjournals.org)
Products1
Non-essential metabolites include metabolites generated through the activation, detoxification and elimination of metabolic by-products or xenobiotics. (biomedcentral.com)
Identification1
A major challenge in biotechnology and biomanufacturing is the identification of a set of biomarkers for perturbations and metabolites of interest. (pnnl.gov)