Date published: 2025-10-20

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N7-(2-Carbamoyl-2-hydroxyethyl)guanine (CAS 163734-06-3)

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Alternate Names:
N7-GA-Gua; 2-Amino-1,6-dihydro-α-hydroxy-6-oxo-7H-purine-7-propanamide
Application:
N7-(2-Carbamoyl-2-hydroxyethyl)guanine is a DNA adduct of glycidamide
CAS Number:
163734-06-3
Molecular Weight:
238.30
Molecular Formula:
C8H10N6O3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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N7-(2-Carbamoyl-2-hydroxyethyl)guanine exerts its effect by specifically binding to enzymes responsible for DNA and RNA synthesis, as well as protein synthesis, leading to their inhibition. This binding occurs at the active site of these enzymes, effectively impeding their catalytic activity in carrying out their respective reactions. Additionally, N7-(2-Carbamoyl-2-hydroxyethyl)guanine also binds to the active site of enzymes involved in transcription and translation, effectively hindering their ability to perform their respective functions.


N7-(2-Carbamoyl-2-hydroxyethyl)guanine (CAS 163734-06-3) References

  1. DNA adduct formation from acrylamide via conversion to glycidamide in adult and neonatal mice.  |  Gamboa da Costa, G., et al. 2003. Chem Res Toxicol. 16: 1328-37. PMID: 14565774
  2. DNA damage and DNA adduct formation in rat tissues following oral administration of acrylamide.  |  Manière, I., et al. 2005. Mutat Res. 580: 119-29. PMID: 15668114
  3. DNA adducts: mass spectrometry methods and future prospects.  |  Farmer, PB., et al. 2005. Toxicol Appl Pharmacol. 207: 293-301. PMID: 15990134
  4. Genotoxicity of acrylamide and glycidamide in human lymphoblastoid TK6 cells.  |  Koyama, N., et al. 2006. Mutat Res. 603: 151-8. PMID: 16387526
  5. Cytogenetic damage induced by acrylamide and glycidamide in mammalian cells: correlation with specific glycidamide-DNA adducts.  |  Martins, C., et al. 2007. Toxicol Sci. 95: 383-90. PMID: 17088317
  6. DNA adduct formation and induction of micronuclei and mutations in B6C3F1/Tk mice treated neonatally with acrylamide or glycidamide.  |  Von Tungeln, LS., et al. 2009. Int J Cancer. 124: 2006-15. PMID: 19123476
  7. Tumorigenicity of acrylamide and its metabolite glycidamide in the neonatal mouse bioassay.  |  Von Tungeln, LS., et al. 2012. Int J Cancer. 131: 2008-15. PMID: 22336951
  8. Toxicokinetics of acrylamide in primary rat hepatocytes: coupling to glutathione is faster than conversion to glycidamide.  |  Watzek, N., et al. 2013. Arch Toxicol. 87: 1545-56. PMID: 23568512
  9. Biomarker analysis of hemoglobin adducts of acrylamide and glycidamide enantiomers for mid-term internal exposure assessment by isotope dilution ultra-high performance liquid chromatography tandem mass spectrometry.  |  Zhang, Y., et al. 2018. Talanta. 178: 825-833. PMID: 29136901
  10. Feasibility of using urinary N7-(2-carbamoyl-2-hydroxyethyl) Guanine as a biomarker for acrylamide exposed workers.  |  Huang, YF., et al. 2018. J Expo Sci Environ Epidemiol. 28: 589-598. PMID: 29463903
  11. Changes of metabolites of acrylamide and glycidamide in acrylamide-exposed rats pretreated with blueberry anthocyanins extract.  |  Wang, P., et al. 2019. Food Chem. 274: 611-619. PMID: 30372986
  12. Interaction of Acrylamide, Acrolein, and 5-Hydroxymethylfurfural with Amino Acids and DNA.  |  Ou, J., et al. 2020. J Agric Food Chem. 68: 5039-5048. PMID: 32275416
  13. Analysis of N7-(2-carbamoyl-2-hydroxyethyl)guanine in dried blood spot after food exposure by Ultra High Performance Liquid Chromatography-Tandem Mass Spectrometry.  |  Harahap, Y., et al. 2022. BMC Chem. 16: 83. PMID: 36324163

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

N7-(2-Carbamoyl-2-hydroxyethyl)guanine, 5 mg

sc-212352
5 mg
$393.00