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A7154

Sigma-Aldrich

Adenosine, periodate oxidized

≥93%

Sinónimos:

ADOX, Adenosine-2′,3′-dialdehyde

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About This Item

Fórmula empírica (notación de Hill):
C10H11N5O4
Número de CAS:
34240-05-6
Peso molecular:
265.23
MDL number:
MFCD00056960
UNSPSC Code:
41106305
PubChem Substance ID:
24891180
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

assay

≥93%

form

powder

solubility

0.2 M HCl: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

SMILES string

Nc1ncnc2n(cnc12)C(OC(CO)C=O)C=O

InChI

1S/C10H11N5O4/c11-9-8-10(13-4-12-9)15(5-14-8)7(3-18)19-6(1-16)2-17/h1,3-7,17H,2H2,(H2,11,12,13)

InChI key

ILMNSCQOSGKTNZ-UHFFFAOYSA-N

Application

Adenosine, periodate oxidized has been used:
  • as a methylarginine transferase inhibitor in the human embryonic kidney (HEK)-293 T cells
  • as a methylase inhibitor in H4 neuroglioma
  • as a broad inhibitor of S-adenosylmethionine (AdoMet)-dependent methyltransferases in mouse embryo fibroblast NIH3T3 cells

Biochem/physiol Actions

Adenosine, periodate oxidized (Adox) is a protein arginine methyltransferases (PRMTs) inhibitor. It also inhibits the enzyme S-adenosylhomocysteine hydrolase and induces apoptosis. Its inhibitory effect on histone methyltransferases prevents histone methylation. Adox also elicits intrinsic cytotoxic properties.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000380921
0000380922
0000380922
0000380921
SLCK3756

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Jessica A Sipkens et al.
Atherosclerosis, 221(1), 48-54 (2011-12-30)
We have previously shown that homocysteine (Hcy) induces phosphatidylserine (PS) exposure, apoptosis and necrosis in human endothelial cells. Since it has been suggested that S-adenosylhomocysteine (SAH) is the main causative factor in Hcy-induced pathogenesis of cardiovascular disease, we evaluate here
Malin Hultberg et al.
Clinical biochemistry, 39(2), 160-163 (2005-12-07)
The metabolism of homocysteine is influenced by several dietary factors, including folate, cobalamin and possibly also the intake of polyhydroxylated phenolic compounds (polyphenols), which were shown to increase plasma homocysteine (tHcy) concentration. In order to reveal the cause of the
Rita Castro et al.
Journal of molecular medicine (Berlin, Germany), 83(10), 831-836 (2005-06-25)
Hyperhomocysteinemia is a risk factor for atherosclerosis and vascular disease; however, the mechanism underlying this association remains poorly understood. Increased levels of intracellular S-adenosylhomocysteine (AdoHcy), secondary to homocysteine-mediated reversal of the AdoHcy hydrolase reaction, have been associated with reduced DNA
Ivon J M van der Linden et al.
Birth defects research. Part A, Clinical and molecular teratology, 82(10), 676-683 (2008-10-22)
An impaired DNA methylation has been suggested to underlie the complex etiology of neural tube defects (NTDs). Previously, we have demonstrated that inhibition of methylation by periodate oxidized adenosine (Adox) results in a widening of the anterior neuropore (ANP) in
Francois H T Duong et al.
Hepatology (Baltimore, Md.), 43(4), 796-806 (2006-03-25)
Hepatitis C virus (HCV) infection is an important cause of chronic liver disease. Standard therapy, pegylated interferon alpha (pegIFNalpha) combined with ribavirin, results in a sustained response rate in approximately half of patients. The cause of treatment failure in the
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