Mercapturic acid

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Mercapturic acids are condensation products formed from the coupling of cysteine with aromatic compounds. [1] They are formed as conjugates in the liver and are excreted in the urine. [1] [2]

Mercapturic acids are formed as part of xenobiotic metabolism. A glutathione S-transferase first conjugates the foreign compound to glutathione, forming an adduct. The adduct is then converted to the mercapturic acid: the γ-glutamate and glycine residues in the glutathione molecule are removed by gamma-glutamyl transpeptidase and dipeptidases. In the final step, the cystine residue in the conjugate is acetylated. The mercapturic acid is then excreted. [3]

Levels of mercapturic acids in urine may be used as an indicator of exposure to, e.g., ethylene dibromide, [4] acrylamide, and terbuthylazine. [5]

Etymology

The name mercapturic acid is a combination of mercapturic and acid. The latter indicates that the compound is an acid. The former is a compound word consisting of the stem mercaptur-, coming from mercaptan, and the suffix -ic, meaning "having the character of". In sum, the name mercapturic acid means "an acid with mercaptan character/nature". [6]

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References

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  3. Boyland E, Chasseaud LF (1969). The Role of Glutathione and Glutathione S-Transferases in Mercapturic Acid Biosynthesis. Advances in Enzymology and Related Areas of Molecular Biology. Vol. 32. pp. 173–219. doi:10.1002/9780470122778.ch5. ISBN   978-0-470-64961-9. PMID   4892500.
  4. Kim DH, Guengerich FP (November 1989). "Excretion of the mercapturic acid S-[2-(N7-guanyl)ethyl]-N-acetylcysteine in urine following administration of ethylene dibromide to rats". Cancer Res. 49 (21): 5843–7. PMID   2790795.
  5. Mercadante R, Polledri E, Fustinoni S (July 2012). "Determination of terbuthylazine and desethylterbuthylazine in human urine and hair samples by eletrospray ionization-liquid chromatography/triple quadrupole mass spectrometry". Analytical and Bioanalytical Chemistry. 404 (3): 875–86. doi:10.1007/s00216-012-6184-3. PMID   22752446. S2CID   2087135.
  6. "Definition of IC". www.merriam-webster.com. 2024-03-26. Retrieved 2024-04-27.