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1,N6-Ethenoadenine (CAS 13875-63-3)

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Alternate Names:
1H-imidazo[2,1-f]purine
Application:
1,N6-Ethenoadenine is a mutagenic DNA lesion
CAS Number:
13875-63-3
Molecular Weight:
159.15
Molecular Formula:
C7H5N5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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1,N6-Ethenoadenine is a fluorescent analog of adenine that is used in biophysical research to study nucleic acid structure, function, and dynamics. It is incorporated into oligonucleotides to investigate the interactions between DNA or RNA strands and proteins, as well as to visualize conformational changes during processes such as replication and transcription. This compound′s sensitivity to the local environment makes it a useful probe for examining the structural aspects of nucleic acids and their complexes with other biomolecules. In fluorescence spectroscopy, 1,N6-Ethenoadenine provides researchers with a tool for monitoring nucleic acid behavior in real-time, which aids in understanding the mechanisms of molecular recognition. Additionally, its incorporation into nucleic acids has been pivotal in the development of new techniques for studying the folding and unfolding pathways of RNA and DNA.


1,N,[object Object],-Ethenoadenine (CAS 13875-63-3) References

  1. Both purified human 1,N6-ethenoadenine-binding protein and purified human 3-methyladenine-DNA glycosylase act on 1,N6-ethenoadenine and 3-methyladenine.  |  Singer, B., et al. 1992. Proc Natl Acad Sci U S A. 89: 9386-90. PMID: 1409645
  2. Chemical rearrangement and repair pathways of 1,N6-ethenoadenine.  |  Speina, E., et al. 2003. Mutat Res. 531: 205-17. PMID: 14637256
  3. Evidence of complete cellular repair of 1,N6-ethenoadenine, a mutagenic and potential damage for human cancer, revealed by a novel method.  |  Choudhury, S., et al. 2008. Mol Cell Biochem. 313: 19-28. PMID: 18373235
  4. The acidity and proton affinity of the damaged base 1,N6-ethenoadenine in the gas phase versus in solution: intrinsic reactivity and biological implications.  |  Liu, M., et al. 2008. J Org Chem. 73: 5907-14. PMID: 18593189
  5. The role of AlkB protein in repair of 1,N⁶-ethenoadenine in Escherichia coli cells.  |  Maciejewska, AM., et al. 2011. Mutagenesis. 26: 401-6. PMID: 21193516
  6. 1,N6-ethenoadenine and other Fluorescent Nucleobase Analogues as Substrates for Purine-Nucleoside Phosphorylases: Spectroscopic and Kinetic Studies.  |  Wierzchowski, J., et al. 2017. Curr Pharm Des.. PMID: 29022509
  7. Formation of 1,N6-ethenoadenine and 3,N4-ethenocytosine by lipid peroxidation products and nucleic acid bases.  |  el Ghissassi, F., et al. 1995. Chem Res Toxicol. 8: 278-83. PMID: 7766812
  8. 1,N6-ethenoadenine is preferred over 3-methyladenine as substrate by a cloned human N-methylpurine-DNA glycosylase (3-methyladenine-DNA glycosylase).  |  Dosanjh, MK., et al. 1994. Biochemistry. 33: 1624-8. PMID: 8110764
  9. Mutagenic and genotoxic effects of three vinyl chloride-induced DNA lesions: 1,N6-ethenoadenine, 3,N4-ethenocytosine, and 4-amino-5-(imidazol-2-yl)imidazole.  |  Basu, AK., et al. 1993. Biochemistry. 32: 12793-801. PMID: 8251500
  10. 1,N6-ethenoadenine and 3,N4-ethenocytosine are excised by separate human DNA glycosylases.  |  Hang, B., et al. 1996. Carcinogenesis. 17: 155-7. PMID: 8565126
  11. Quantitation of 1,N6-ethenoadenine in rat urine by immunoaffinity extraction combined with liquid chromatography/electrospray ionization mass spectrometry.  |  Yen, TY., et al. 1998. Chem Res Toxicol. 11: 810-5. PMID: 9671544
  12. Detection of 1,N6-ethenoadenine in rat urine after chloroethylene oxide exposure.  |  Holt, S., et al. 1998. Carcinogenesis. 19: 1763-9. PMID: 9806156
  13. DNA adducts of 2,3-epoxy-4-hydroxynonanal: detection of 7-(1', 2'-dihydroxyheptyl)-3H-imidazo[2,1-i]purine and 1,N6-ethenoadenine by gas chromatography/negative ion chemical ionization/mass spectrometry.  |  Chen, HJ., et al. 1998. Chem Res Toxicol. 11: 1474-80. PMID: 9860490

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

1,N6-Ethenoadenine, 1 mg

sc-206264
1 mg
$372.00

1,N6-Ethenoadenine, 2 mg

sc-206264A
2 mg
$576.00

1,N6-Ethenoadenine, 5 mg

sc-206264B
5 mg
$923.00

1,N6-Ethenoadenine, 10 mg

sc-206264C
10 mg
$1433.00

1,N6-Ethenoadenine, 25 mg

sc-206264D
25 mg
$3065.00