Home Other Building Blocks 2'-deoxy-7,8-dihydro-8-oxoadenosine

2'-deoxy-7,8-dihydro-8-oxoadenosine

CAS No.:
62471-63-0
Catalog Number:
AG00EEQA
Molecular Formula:
Molecular Weight:
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Product Description
Catalog Number:
AG00EEQA
Chemical Name:
2'-deoxy-7,8-dihydro-8-oxoadenosine
CAS Number:
62471-63-0
MDL Number:
MFCD03788704
IUPAC Name:
6-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-purin-8-one
InChI:
InChI=1S/C10H13N5O4/c11-8-7-9(13-3-12-8)15(10(18)14-7)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H,14,18)(H2,11,12,13)/t4-,5+,6+/m0/s1
InChI Key:
NDWAUKFSFFRGLF-KVQBGUIXSA-N
Properties
Complexity:
370  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
267.097g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
267.245g/mol
Monoisotopic Mass:
267.097g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
134A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.5  
Literature
Title Journal
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8-Oxo-7,8-dihydrodeoxyadenosine: the first example of a native DNA lesion that stabilizes human telomeric G-quadruplex DNA. Biochemical and biophysical research communications 20120518
Catechol metabolites of zeranol and 17β-estradiol: a comparative in vitro study on the induction of oxidative DNA damage and methylation by catechol-O-methyltransferase. Toxicology letters 20120405
Harmonising measurements of 8-oxo-7,8-dihydro-2'-deoxyguanosine in cellular DNA and urine. Free radical research 20120401
The mutagenic potential of 8-oxoG/single strand break-containing clusters depends on their relative positions. Mutation research 20120401
Biomarker analysis for prostate cancer diagnosis using LC-MS and CE-MS. Bioanalysis 20110901
Effect of surgical stress on nuclear and mitochondrial DNA from healthy sections of colon and rectum of patients with colorectal cancer. Journal of biosciences 20110601
Divergent effects of oxidatively induced modification to the C8 of 2'-deoxyadenosine on transcription factor binding: 8,5'(S)-cyclo-2'-deoxyadenosine inhibits the binding of multiple sequence specific transcription factors, while 8-oxo-2'-deoxyadenosine increases binding of CREB and NF-kappa B to DNA. Environmental and molecular mutagenesis 20110501
Aberrations in one-carbon metabolism induce oxidative DNA damage in sporadic breast cancer. Molecular and cellular biochemistry 20110301
Radical chemistry of 8-oxo-7,8-dihydro-2'-deoxyadenosine and 8-oxo-7,8-dihydro-2'-deoxyguanosine: a pulse radiolysis study. The journal of physical chemistry. B 20101216
Sulfur mustard analog induces oxidative stress and activates signaling cascades in the skin of SKH-1 hairless mice. Free radical biology & medicine 20091201
Elevated level of 8-oxo-7,8-dihydro-2'-deoxyguanosine in leukocytes of BRCA1 mutation carriers compared to healthy controls. International journal of cancer 20091101
Simultaneous determination of 8-oxo-2'-deoxyguanosine and 8-oxo-2'-deoxyadenosine in DNA using online column-switching liquid chromatography/tandem mass spectrometry. Rapid communications in mass spectrometry : RCM 20090101
Inhibition of Rac and Rac-linked functions by 8-oxo-2'-deoxyguanosine in murine macrophages. Free radical research 20090101
Determination of 8-hydroxy-2'deoxyguanosine in urine using HPLC with electrochemical detection. Arhiv za higijenu rada i toksikologiju 20081201
Analysis of urinary 8-oxo-7,8-dihydro-purine-2'-deoxyribonucleosides by LC-MS/MS and improved ELISA. Free radical research 20081001
Efficient removal of formamidopyrimidines by 8-oxoguanine glycosylases. Biochemistry 20080122
Studies on the replication of the ring opened formamidopyrimidine, Fapy.dG in Escherichia coli. Biochemistry 20070904
The in vivo antioxidant action and the reduction of oxidative stress by boysenberry extract is dependent on base diet constituents in rats. Journal of medicinal food 20070601
Activity of OGG1 variants in the repair of pro-oxidant-induced 8-oxo-2'-deoxyguanosine. DNA repair 20061108
Recognition of oxidatively modified bases within the biotin-binding site of avidin. Journal of molecular biology 20060317
The mechanism of guanine specific photooxidation in the presence of berberine and palmatine: activation of photosensitized singlet oxygen generation through DNA-binding interaction. Chemical research in toxicology 20051001
Nitrative and oxidative DNA damage in oral lichen planus in relation to human oral carcinogenesis. Cancer science 20050901
Structure-activity relationship of phosmidosine: importance of the 7,8-dihydro-8-oxoadenosine residue for antitumor activity. Bioorganic & medicinal chemistry 20041001
Oxidative DNA damage induced by benz[a]anthracene metabolites via redox cycles of quinone and unique non-quinone. Chemical research in toxicology 20031101
Oxidative stress in lung epithelial cells from patients with idiopathic interstitial pneumonias. The European respiratory journal 20030201
Metal-mediated DNA damage induced by curcumin in the presence of human cytochrome P450 isozymes. Archives of biochemistry and biophysics 20020915
Base pairing properties of 8-oxo-7,8-dihydroadenosine in cDNA synthesis by reverse transcriptases. Bioorganic & medicinal chemistry letters 20020805
Urinary excretion of 8-oxo-7, 8-dihydro-2'-deoxyguanosine as a predictor of the development of diabetic nephropathy. Diabetologia 20020601
A comparative photomechanistic study (spin trapping, EPR spectroscopy, transient kinetics, photoproducts) of nucleoside oxidation (dG and 8-oxodG) by triplet-excited acetophenones and by the radicals generated from alpha-oxy-substituted derivatives through Norrish-type I cleavage. Journal of the American Chemical Society 20020417
Protective effect of phytic acid on oxidative DNA damage with reference to cancer chemoprevention. Biochemical and biophysical research communications 20011102
Photobleaching of asymmetric cyanines used for fluorescence imaging of single DNA molecules. Journal of the American Chemical Society 20010822
Measurement of 8-oxo-2'-deoxyguanosine and 8-oxo-2'-deoxyadenosine in DNA and human urine by high performance liquid chromatography-electrospray tandem mass spectrometry. Free radical biology & medicine 20010401
Properties