CAS 68498-25-9

Ethenodeoxyadenosine

Description:

Ethenodeoxyadenosine, also known as 2'-deoxy-2'-ethenoadenosine, is a modified nucleoside that features an etheno group at the 2' position of the ribose sugar. This compound is characterized by its structural similarity to adenosine, with the addition of the etheno group, which can influence its biological activity and stability. Ethenodeoxyadenosine is often studied in the context of nucleic acid chemistry and molecular biology due to its potential role in the formation of cross-links in DNA, which can affect replication and transcription processes. The presence of the etheno modification can also impact the binding affinity of nucleosides to their respective receptors or enzymes. This compound is of interest in research related to mutagenesis and the development of therapeutic agents, particularly in cancer research, where DNA modifications play a crucial role in the efficacy of certain treatments. Its CAS number, 68498-25-9, is used for identification in chemical databases and regulatory contexts.

Formula: C₁₂H₁₃N₅O₃

InChI: InChI=1/C12H13N5O3/c18-4-8-7(19)3-9(20-8)17-6-14-10-11-13-1-2-16(11)5-15-12(10)17/h1-2,5-9,18-19H,3-4H2

InChI key: InChIKey=XQQIMTUYVDUWKJ-DJLDLDEBSA-N

SMILES: C(O)[C@H]1O[C@@H](N2C3=C(C=4N(C=N3)C=CN4)N=C2)C[C@@H]1O

Synonyms:

• 1,N(6)-Ethenodeoxyadenosine
• 1,N6-Ethenodeoxyadenosine
• 1,N⁶-Etheno-2′-deoxyadenosine
• 1,N⁶-Etheno-dA
• 1,N⁶-Ethenodeoxyadenosine
• 3-(2-Deoxy-beta-D-erythro-pentofuranosyl)-3H-imidazo(2,1-i)purine
• 3-(2-Deoxy-β-<span class="text-smallcaps">D</span>-erythro-pentofuranosyl)-3H-imidazo[2,1-i]purine
• 3-(2-deoxypentofuranosyl)-3H-imidazo[2,1-i]purine
• 3H-Imidazo(2,1-i)purine, 3-(2-deoxy-beta-D-erythro-pentofuranosyl)-
• 3H-Imidazo[2,1-i]purine, 3-(2-deoxy-β-<span class="text-smallcaps">D</span>-erythro-pentofuranosyl)-
• Ccris 2746
• Ethenodeoxyadenosine
• N¹,N⁶-Etheno-2′-deoxyadenosine
• 3-(2-Deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo[2,1-i]purine
• 3H-Imidazo[2,1-i]purine, 3-(2-deoxy-β-D-erythro-pentofuranosyl)-
• 1,N6-Etheno-2′-deoxyadenosine
• 6-(2-Deoxy-β-D-ribofuranosyl)-1,3a,5,6,8-pentaaza-3aH,6H-as-indacene
• 3-(2-Deoxy-β-D-ribofuranosyl)-3H-imidazo[2,1-i]purine
• ETHENO-2'-DEOXYADENOSINE
• N,1-(Ethene-1,2-diyl)-1,6-dihydro-6,N-didehydro-2'-deoxyadenosine
• Etheno-2’-deoxy-β-D-adenosine
• N6-Etheno 2'-deoxyadenosine
• 1,N(sup 6)-etheno-2'-deoxyadenosine
• N
• 3H-Imidazo[2,1-i]purine, 3-(2-deoxy--D-ery)
• 1,N6-Etheno-dA
• N1,N6-Etheno-2'-deoxyadenosine
• ETHENO-2'-DEOXYADENOSINE, MORPURE HPLC PURIFIED, DELIVERED >= 98% PURE WITH HPLC UV CHROMATOGRAM
• N,1-Etheno-2'-deoxyadenosine
• Etheno-2'-deoxy-β-D-adenosine
• -Etheno-2'-deoxyadenosine
• 2ˊ-Deoxy-1,N6-ethenoadenosine
• 6

(2R,3S,5R)-2-(Hydroxymethyl)-5-(3H-imidazo[2,1-i]purin-3-yl)tetrahydrofuran-3-ol

CAS: 68498-25-9

(2R,3S,5R)-2-(Hydroxymethyl)-5-(3H-imidazo[2,1-i]purin-3-yl)tetrahydrofuran-3-ol

Purity: 99%

Molecular weight: 275.27g/mol

Ref: 54-OR1074636

N6-Etheno 2''-deoxyadenosine

CAS: 68498-25-9

Formula: C₁₂H₁₃N₅O₃

Purity: ≥ 98.0% (anhydrous basis)

Color and Shape: White to off-white powder

Molecular weight: 275.26

Ref: 7W-GN5101

Etheno-2’-deoxy-β-D-adenosine

Controlled Product

CAS: 68498-25-9

Stability Hygroscopic
Applications An etheno DNA-adduct of adenosine found in atherosclerotic lesions in aorta smooth muscle cells induced via lipid peroxidation. A biomarker for genotoxicity.
References Nair, J. et al.: Mut. Res. Fund. Mol. Mech. Mutagen., 621, 95 (2007); Meerang, M. et al.: Free Rad. Biol. Med., 44, 1863 (2008); Brink, A. et al.: Mut. Res. Gen. Toxicol. Env. Mutagen., 678, 123 (2009);

Formula: C₁₂H₁₃N₅O₃

Color and Shape: Neat

Molecular weight: 275.26

Ref: TR-E890380

N6-Etheno 2'-deoxyadenosine

CAS: 68498-25-9

N6-Etheno 2'-deoxyadenosine is a nucleoside analogue that inhibits DNA synthesis by binding to the enzyme thymidylate synthase, which catalyzes the conversion of deoxyuridine monophosphate to thymidine monophosphate. This drug has been shown to be genotoxic in vitro and in vivo, as evidenced by its ability to induce chromosomal aberrations in cultured human lymphocytes and disrupt DNA replication in mammalian cells. It also reacts with mismatched base pairs and dna duplexes, leading to their degradation. N6-Etheno 2'-deoxyadenosine binds reversibly to antibodies and can be detected using an analytical method that employs monoclonal antibodies.

Formula: C₁₂H₁₃N₅O₃

Color and Shape: White Off-White Powder

Molecular weight: 275.26 g/mol

Ref: 3D-NE06241

N6-Etheno 2'-deoxyadenosine

CAS: 68498-25-9

N6-Etheno 2'-deoxyadenosine is used as a biomarker to evaluate chronic inflammation and lipid peroxidation in animal or human tissues.

Formula: C₁₂H₁₃N₅O₃

Purity: 98%

Color and Shape: Solid

Molecular weight: 275.26

Ref: TM-T19465

Etheno-2'-deoxy-β-D-adenosine

CAS: 68498-25-9

Formula: C₁₂H₁₃N₅O₃

Molecular weight: 275.26

Ref: ST-EA-CP-E293006