Home Other Building Blocks 8-HYDROXYGUANOSINE

8-HYDROXYGUANOSINE

CAS No.:
3868-31-3
Catalog Number:
AG00BYFT
Molecular Formula:
C10H13N5O6
Molecular Weight:
299.2401
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$96
- +
5mg
99%
1 week
United States
$161
- +
10mg
99%
1 week
United States
$237
- +
50mg
99%
1 week
United States
$578
- +
100mg
99%
1 week
United States
$960
- +
Product Description
Catalog Number:
AG00BYFT
Chemical Name:
8-HYDROXYGUANOSINE
CAS Number:
3868-31-3
Molecular Formula:
C10H13N5O6
Molecular Weight:
299.2401
MDL Number:
MFCD00216136
IUPAC Name:
2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,7-dihydropurine-6,8-dione
InChI:
InChI=1S/C10H13N5O6/c11-9-13-6-3(7(19)14-9)12-10(20)15(6)8-5(18)4(17)2(1-16)21-8/h2,4-5,8,16-18H,1H2,(H,12,20)(H3,11,13,14,19)/t2-,4-,5-,8-/m1/s1
InChI Key:
FPGSEBKFEJEOSA-UMMCILCDSA-N
SMILES:
OCC1OC(C(C1O)O)n1c(=O)[nH]c2c1nc(N)[nH]c2=O
Properties
Complexity:
574  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
299.087g/mol
Formal Charge:
0
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0
Molecular Weight:
299.243g/mol
Monoisotopic Mass:
299.087g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
170A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.6  
Literature
Title Journal
Experimental evidence of oxidative stress in patients with l-2-hydroxyglutaric aciduria and that l-carnitine attenuates in vitro DNA damage caused by d-2-hydroxyglutaric and l-2-hydroxyglutaric acids. Toxicology in vitro : an international journal published in association with BIBRA 20170801
Oxidative damage of DNA, RNA and their metabolites in leukocytes, plasma and urine of Macaca mulatta: 8-oxoguanosine in urine is a useful marker for aging. Free radical research 20120901
Age-dependent increases in the oxidative damage of DNA, RNA, and their metabolites in normal and senescence-accelerated mice analyzed by LC-MS/MS: urinary 8-oxoguanosine as a novel biomarker of aging. Free radical biology & medicine 20120501
RNA modifications by oxidation: a novel disease mechanism? Free radical biology & medicine 20120415
Lifetimes and reaction pathways of guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions. Journal of the American Chemical Society 20120314
Oxidative damage to guanine nucleosides following combination chemotherapy with 5-fluorouracil and oxaliplatin. Cancer chemotherapy and pharmacology 20120201
Long-term perturbation of muscle iron homeostasis following hindlimb suspension in old rats is associated with high levels of oxidative stress and impaired recovery from atrophy. Experimental gerontology 20120101
Accumulation of exogenous amyloid-beta peptide in hippocampal mitochondria causes their dysfunction: a protective role for melatonin. Oxidative medicine and cellular longevity 20120101
Structure of a Nudix hydrolase (MutT) in the Mg(2+)-bound state from Bartonella henselae, the bacterium responsible for cat scratch fever. Acta crystallographica. Section F, Structural biology and crystallization communications 20110901
Genetic and environmental influences on oxidative damage assessed in elderly Danish twins. Free radical biology & medicine 20110601
Characterization of 2'-deoxyguanosine oxidation products observed in the Fenton-like system Cu(II)/H2O2/reductant in nucleoside and oligodeoxynucleotide contexts. Organic & biomolecular chemistry 20110507
Long-term effects of Irbesartan treatment and smoking on nucleic acid oxidation in patients with type 2 diabetes and microalbuminuria: an Irbesartan in patients with type 2 diabetes and Microalbuminuria (IRMA 2) substudy. Diabetes care 20110501
Carcinogenic heavy metals, As3+ and Cr6+, increase affinity of nuclear mono-ubiquitinated annexin A1 for DNA containing 8-oxo-guanosine, and promote translesion DNA synthesis. Toxicology and applied pharmacology 20110415
Reference ranges of urinary biomarkers of oxidized guanine in (2'-deoxy)ribonucleotides and nucleic acids. Free radical biology & medicine 20110115
NAD(P)H: quinone oxidoreductase 1 deficiency conjoint with marginal vitamin C deficiency causes cigarette smoke induced myelodysplastic syndromes. PloS one 20110101
Association between urinary excretion of cortisol and markers of oxidatively damaged DNA and RNA in humans. PloS one 20110101
Use of specific chemical reagents for detection of modified nucleotides in RNA. Journal of nucleic acids 20110101
Calpain and PARP activation during photoreceptor cell death in P23H and S334ter rhodopsin mutant rats. PloS one 20110101
Pathogenic triad in COPD: oxidative stress, protease-antiprotease imbalance, and inflammation. International journal of chronic obstructive pulmonary disease 20110101
Intestinal metaplasia -the effect of Acid on the gastric mucosa and gastric carcinogenesis-. Journal of toxicologic pathology 20100901
Oxidative damage to DNA and lipids as biomarkers of exposure to air pollution. Environmental health perspectives 20100801
A nuclear family A DNA polymerase from Entamoeba histolytica bypasses thymine glycol. PLoS neglected tropical diseases 20100801
Quantitative determination of urinary 8-oxo-7,8-dihydro-2'-deoxyguanosine, 8-oxo-7,8-dihydroguanine, 8-oxo-7,8-dihydroguanosine, and their non-oxidized forms: daily concentration profile in healthy volunteers. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals 20100501
Occupational exposure to low levels of benzene: Biomarkers of exposure and nucleic acid oxidation and their modulation by polymorphic xenobiotic metabolizing enzymes. Toxicology letters 20100401
Hydrogen sulfide induces oxidative damage to RNA and DNA in a sulfide-tolerant marine invertebrate. Physiological and biochemical zoology : PBZ 20100101
Urinary excretion of biomarkers of oxidatively damaged DNA and RNA in hereditary hemochromatosis. Free radical biology & medicine 20091015
Biomarkers of nucleic acid oxidation, polymorphism in, and expression of, hOGG1 gene in styrene-exposed workers. Toxicology letters 20091008
Automated method for the direct analysis of 8-oxo-guanosine and 8-oxo-2'-deoxyguanosine in human urine using ultraperformance liquid chromatography and tandem mass spectrometry. Free radical biology & medicine 20090901
Incorporation of 8-hydroxyguanosine (8-oxo-7,8-dihydroguanosine) 5'-triphosphate by bacterial and human RNA polymerases. Free radical biology & medicine 20090615
Coronary intraplaque hemorrhage evokes a novel atheroprotective macrophage phenotype. The American journal of pathology 20090301
Structure of human DNA polymerase kappa inserting dATP opposite an 8-OxoG DNA lesion. PloS one 20090101
Messenger RNA oxidation occurs early in disease pathogenesis and promotes motor neuron degeneration in ALS. PloS one 20080101
Iron accumulation with age, oxidative stress and functional decline. PloS one 20080101
Lack of association of colonic epithelium telomere length and oxidative DNA damage in Type 2 diabetes under good metabolic control. BMC endocrine disorders 20080101
AtNUDX1, an 8-oxo-7,8-dihydro-2'-deoxyguanosine 5'-triphosphate pyrophosphohydrolase, is responsible for eliminating oxidized nucleotides in Arabidopsis. Plant & cell physiology 20071001
Cyclophosphamide-induced apoptosis in COV434 human granulosa cells involves oxidative stress and glutathione depletion. Toxicological sciences : an official journal of the Society of Toxicology 20070701
In vitro ligation of oligodeoxynucleotides containing C8-oxidized purine lesions using bacteriophage T4 DNA ligase. Biochemistry 20070327
Effect of olive oils on biomarkers of oxidative DNA stress in Northern and Southern Europeans. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20070101
A method to determine RNA and DNA oxidation simultaneously by HPLC-ECD: greater RNA than DNA oxidation in rat liver after doxorubicin administration. Biological chemistry 20060101
Hepatic oxidative stress during aging: effects of 8% long-term calorie restriction and lifelong exercise. Antioxidants & redox signaling 20060101
Consequences of low birthweight on urinary excretion of DNA markers of oxidative stress in young men. Scandinavian journal of clinical and laboratory investigation 20060101
A lysine residue in the fingers subdomain of T7 DNA polymerase modulates the miscoding potential of 8-oxo-7,8-dihydroguanosine. Structure (London, England : 1993) 20051101
Characterization of 5-hydroxy-8-oxo-7,8-dihydroguanosine in the photosensitized oxidation of 8-oxo-7,8-dihydroguanosine and its rearrangement to spiroiminodihydantoin. Journal of the American Chemical Society 20041229
DNA . RNA heteroduplex containing 8-oxo-7,8-dihydroguanosine: base pairing, structures, and thermodynamic stability. Journal of biochemistry and molecular biology 20041130
Spermine participates in oxidative damage of guanosine and 8-oxoguanosine leading to deoxyribosylurea formation. Journal of the American Chemical Society 20040811
Photochemical cross-linking of Escherichia coli Fpg protein to DNA duplexes containing phenyl(trifluoromethyl)diazirine groups. European journal of biochemistry 20030701
Use of crosslinking for revealing the DNA phosphate groups forming specific contacts with the E. coli Fpg protein. Biochimie 20030501
Low-temperature photosensitized oxidation of a guanosine derivative and formation of an imidazole ring-opened product. Journal of the American Chemical Society 20020417
Formation of 8-nitroguanosine in cellular RNA as a biomarker of exposure to reactive nitrogen species. Chemico-biological interactions 20020220
The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine. Organic letters 20010906
Characterization of hydantoin products from one-electron oxidation of 8-oxo-7,8-dihydroguanosine in a nucleoside model. Chemical research in toxicology 20010701
Spiroiminodihydantoin is the major product of the 8-oxo-7,8-dihydroguanosine reaction with peroxynitrite in the presence of thiols and guanosine photooxidation by methylene blue. Organic letters 20010405
Increased oxidative DNA damage in mammary tumor cells by continuous epidermal growth factor stimulation. Journal of the National Cancer Institute 20010207
Properties