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3868-31-3,MFCD00216136
Catalog No.:AA00BYD1

3868-31-3 | 8-HYDROXYGUANOSINE

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1mg
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5mg
98%
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10mg
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$224.00   $157.00
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25mg
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50mg
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100mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BYD1
Chemical Name:
8-HYDROXYGUANOSINE
CAS Number:
3868-31-3
Molecular Formula:
C10H13N5O6
Molecular Weight:
299.2401
MDL Number:
MFCD00216136
SMILES:
OCC1OC(C(C1O)O)n1c(=O)[nH]c2c1nc(N)[nH]c2=O
Properties
Properties
 
Form:
Solid  
MP:
>200°C (dec.)  
Storage:
Room Temperature;  

Computed Properties
 
Complexity:
574  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
6  
Rotatable Bond Count:
2  
XLogP3:
-3.6  

Downstream Synthesis Route

[1]JournalofMedicinalChemistry,1985,vol.28,p.1194-1198

Literature

Title: 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.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20170801

Title: 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.

Journal: Free radical research 20120901

Title: 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.

Journal: Free radical biology & medicine 20120501

Title: RNA modifications by oxidation: a novel disease mechanism?

Journal: Free radical biology & medicine 20120415

Title: Lifetimes and reaction pathways of guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions.

Journal: Journal of the American Chemical Society 20120314

Title: Oxidative damage to guanine nucleosides following combination chemotherapy with 5-fluorouracil and oxaliplatin.

Journal: Cancer chemotherapy and pharmacology 20120201

Title: 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.

Journal: Experimental gerontology 20120101

Title: Accumulation of exogenous amyloid-beta peptide in hippocampal mitochondria causes their dysfunction: a protective role for melatonin.

Journal: Oxidative medicine and cellular longevity 20120101

Title: Structure of a Nudix hydrolase (MutT) in the Mg(2+)-bound state from Bartonella henselae, the bacterium responsible for cat scratch fever.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20110901

Title: Genetic and environmental influences on oxidative damage assessed in elderly Danish twins.

Journal: Free radical biology & medicine 20110601

Title: Characterization of 2'-deoxyguanosine oxidation products observed in the Fenton-like system Cu(II)/H2O2/reductant in nucleoside and oligodeoxynucleotide contexts.

Journal: Organic & biomolecular chemistry 20110507

Title: 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.

Journal: Diabetes care 20110501

Title: 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.

Journal: Toxicology and applied pharmacology 20110415

Title: Reference ranges of urinary biomarkers of oxidized guanine in (2'-deoxy)ribonucleotides and nucleic acids.

Journal: Free radical biology & medicine 20110115

Title: NAD(P)H: quinone oxidoreductase 1 deficiency conjoint with marginal vitamin C deficiency causes cigarette smoke induced myelodysplastic syndromes.

Journal: PloS one 20110101

Title: Association between urinary excretion of cortisol and markers of oxidatively damaged DNA and RNA in humans.

Journal: PloS one 20110101

Title: Use of specific chemical reagents for detection of modified nucleotides in RNA.

Journal: Journal of nucleic acids 20110101

Title: Calpain and PARP activation during photoreceptor cell death in P23H and S334ter rhodopsin mutant rats.

Journal: PloS one 20110101

Title: Pathogenic triad in COPD: oxidative stress, protease-antiprotease imbalance, and inflammation.

Journal: International journal of chronic obstructive pulmonary disease 20110101

Title: Intestinal metaplasia -the effect of Acid on the gastric mucosa and gastric carcinogenesis-.

Journal: Journal of toxicologic pathology 20100901

Title: Oxidative damage to DNA and lipids as biomarkers of exposure to air pollution.

Journal: Environmental health perspectives 20100801

Title: A nuclear family A DNA polymerase from Entamoeba histolytica bypasses thymine glycol.

Journal: PLoS neglected tropical diseases 20100801

Title: 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.

Journal: Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals 20100501

Title: Occupational exposure to low levels of benzene: Biomarkers of exposure and nucleic acid oxidation and their modulation by polymorphic xenobiotic metabolizing enzymes.

Journal: Toxicology letters 20100401

Title: Hydrogen sulfide induces oxidative damage to RNA and DNA in a sulfide-tolerant marine invertebrate.

Journal: Physiological and biochemical zoology : PBZ 20100101

Title: Urinary excretion of biomarkers of oxidatively damaged DNA and RNA in hereditary hemochromatosis.

Journal: Free radical biology & medicine 20091015

Title: Biomarkers of nucleic acid oxidation, polymorphism in, and expression of, hOGG1 gene in styrene-exposed workers.

Journal: Toxicology letters 20091008

Title: 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.

Journal: Free radical biology & medicine 20090901

Title: Incorporation of 8-hydroxyguanosine (8-oxo-7,8-dihydroguanosine) 5'-triphosphate by bacterial and human RNA polymerases.

Journal: Free radical biology & medicine 20090615

Title: Coronary intraplaque hemorrhage evokes a novel atheroprotective macrophage phenotype.

Journal: The American journal of pathology 20090301

Title: Structure of human DNA polymerase kappa inserting dATP opposite an 8-OxoG DNA lesion.

Journal: PloS one 20090101

Title: Messenger RNA oxidation occurs early in disease pathogenesis and promotes motor neuron degeneration in ALS.

Journal: PloS one 20080101

Title: Iron accumulation with age, oxidative stress and functional decline.

Journal: PloS one 20080101

Title: Lack of association of colonic epithelium telomere length and oxidative DNA damage in Type 2 diabetes under good metabolic control.

Journal: BMC endocrine disorders 20080101

Title: AtNUDX1, an 8-oxo-7,8-dihydro-2'-deoxyguanosine 5'-triphosphate pyrophosphohydrolase, is responsible for eliminating oxidized nucleotides in Arabidopsis.

Journal: Plant & cell physiology 20071001

Title: Cyclophosphamide-induced apoptosis in COV434 human granulosa cells involves oxidative stress and glutathione depletion.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20070701

Title: In vitro ligation of oligodeoxynucleotides containing C8-oxidized purine lesions using bacteriophage T4 DNA ligase.

Journal: Biochemistry 20070327

Title: Effect of olive oils on biomarkers of oxidative DNA stress in Northern and Southern Europeans.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20070101

Title: A method to determine RNA and DNA oxidation simultaneously by HPLC-ECD: greater RNA than DNA oxidation in rat liver after doxorubicin administration.

Journal: Biological chemistry 20060101

Title: Hepatic oxidative stress during aging: effects of 8% long-term calorie restriction and lifelong exercise.

Journal: Antioxidants & redox signaling 20060101

Title: Consequences of low birthweight on urinary excretion of DNA markers of oxidative stress in young men.

Journal: Scandinavian journal of clinical and laboratory investigation 20060101

Title: A lysine residue in the fingers subdomain of T7 DNA polymerase modulates the miscoding potential of 8-oxo-7,8-dihydroguanosine.

Journal: Structure (London, England : 1993) 20051101

Title: 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: Journal of the American Chemical Society 20041229

Title: DNA . RNA heteroduplex containing 8-oxo-7,8-dihydroguanosine: base pairing, structures, and thermodynamic stability.

Journal: Journal of biochemistry and molecular biology 20041130

Title: Spermine participates in oxidative damage of guanosine and 8-oxoguanosine leading to deoxyribosylurea formation.

Journal: Journal of the American Chemical Society 20040811

Title: Photochemical cross-linking of Escherichia coli Fpg protein to DNA duplexes containing phenyl(trifluoromethyl)diazirine groups.

Journal: European journal of biochemistry 20030701

Title: Use of crosslinking for revealing the DNA phosphate groups forming specific contacts with the E. coli Fpg protein.

Journal: Biochimie 20030501

Title: Low-temperature photosensitized oxidation of a guanosine derivative and formation of an imidazole ring-opened product.

Journal: Journal of the American Chemical Society 20020417

Title: Formation of 8-nitroguanosine in cellular RNA as a biomarker of exposure to reactive nitrogen species.

Journal: Chemico-biological interactions 20020220

Title: The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine.

Journal: Organic letters 20010906

Title: Characterization of hydantoin products from one-electron oxidation of 8-oxo-7,8-dihydroguanosine in a nucleoside model.

Journal: Chemical research in toxicology 20010701

Title: 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.

Journal: Organic letters 20010405

Title: Increased oxidative DNA damage in mammary tumor cells by continuous epidermal growth factor stimulation.

Journal: Journal of the National Cancer Institute 20010207

Title: Fiala ES, et al. Oxidative DNA and RNA damage in the livers of Sprague-Dawley rats treated with the hepatocarcinogen 2-nitropropane. Cancer Res. 1989 Oct 15;49(20):5518-22.

Title: Abe T, et al. Remarkable increase in the concentration of 8-hydroxyguanosine in cerebrospinal fluid from patients with Alzheimer's disease. J Neurosci Res. 2002 Nov 1;70(3):447-50.

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Tags:3868-31-3 Molecular Formula|3868-31-3 MDL|3868-31-3 SMILES|3868-31-3 8-HYDROXYGUANOSINE