Acrylamide biotransformation and exposure biomarkers (Homo sapiens)

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1DNAKidney and Urinary TractAA-GSHGlutathioneCYP2E1Acrylamide (AA)N7-GA-GuanineValineAAMAAA-ValGlycidamide (GA)GAMAGA-ValN3-GA-AdenosineGA-GSHLiverGenotoxicity and carcinogenicityUrinary biomarkersBlood biomarkers


Description

Acrylamide (AA) is absorbed from the gastrointestinal tract and is converted to toxic glycidamide (GA) by cytochrome P450 2E1. Both AA and GA are coupled with glutathione (GSH) in the liver to form conjugates that are metabolized in the kidney and urinary tract to form modified merbapturic acids (AAMA and GAMA) that serve as biomarkers for AA in urine. Meanwhile, haemoglobin adducts are formed in the blood, including AA-Valine and GA-Valine. Genotoxic and carcinogenic activity is mediated by GA and the formation of DNA adducts with guanine and adenosine.

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Bibliography

  1. Rietjens IMCM, Dussort P, Günther H, Hanlon P, Honda H, Mally A, O'Hagan S, Scholz G, Seidel A, Swenberg J, Teeguarden J, Eisenbrand G; ''Exposure assessment of process-related contaminants in food by biomarker monitoring.''; Arch Toxicol, 2018 PubMed Europe PMC Scholia

History

View all...
CompareRevisionActionTimeUserComment
117644view11:41, 22 May 2021EweitzModified title
96528view08:54, 17 March 2018EgonwReplaced secondary ChEBI identifiers with primary identifiers.
96526view00:27, 17 March 2018AlexanderPicoOntology Term : 'phase I biotransformation pathway via cytochrome P450' added !
96525view00:26, 17 March 2018AlexanderPicoOntology Term : 'glutathione conjugates processing - the mercapturic acid pathway' added !
96524view00:25, 17 March 2018AlexanderPicoOntology Term : 'classic metabolic pathway' added !
96523view00:25, 17 March 2018AlexanderPicoOntology Term : 'hepatocyte' added !
96522view00:24, 17 March 2018AlexanderPicoOntology Term : 'kidney cell' added !
96521view00:23, 17 March 2018AlexanderPicoNew pathway

External references

DataNodes

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NameTypeDatabase referenceComment
AA-GSHMetabolite
AA-ValMetabolite29332409 (Chemspider)
AAMAMetabolite138886 (Chemspider)
Acrylamide (AA)MetaboliteCHEBI:28619 (ChEBI)
CYP2E1GeneProduct1571 (Entrez Gene)
GA-GSHMetabolite
GA-ValMetabolite28573496 (Chemspider)
GAMAMetabolite57262168 (Chemspider)
GlutathioneMetaboliteCHEBI:16856 (ChEBI)
Glycidamide (GA)Metabolite91550 (PubChem-compound)
N3-GA-AdenosineMetabolite
N7-GA-GuanineMetabolite
ValineMetaboliteCHEBI:16414 (ChEBI)

Annotated Interactions

No annotated interactions

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