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H5653

Sigma-Aldrich

8-Hydroxy-2′-deoxyguanosine

≥98% (TLC)

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Synonym(s):
8-Oxo-7,8-dihydro-2′-deoxyguanosine, 8-Oxo-dG
Empirical Formula (Hill Notation):
C10H13N5O5
CAS Number:
Molecular Weight:
283.24
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (TLC)

storage temp.

2-8°C

SMILES string

O=C1C(NC(N2C3CC(O)C(CO)O3)=O)=C2NC(N)=N1

InChI

1S/C10H13N5O5/c11-9-13-7-6(8(18)14-9)12-10(19)15(7)5-1-3(17)4(2-16)20-5/h3-5,16-17H,1-2H2,(H,12,19)(H3,11,13,14,18)

InChI key

HCAJQHYUCKICQH-UHFFFAOYSA-N

Application

8-Hydroxy-2′-deoxyguanosine has been used:
  • as a standard to analyse the oxidative DNA damage in the placenta of normal and abnormal pregnancies by electrochemical detection
  • as a standard for high performance liquid chromatography (HPLC) with electrochemical detection (ECD) measurement
  • as a standard for HPLC and as a urinary marker of oxidative stress in order to assess the potential antioxidant activity of green coffee bean extract (GCBE) in vivo
  • as a standard for LC/MS/MS analysis

Biochem/physiol Actions

A marker compound typically indicative of DNA damage associated with mutagenesis and carcinogenesis
The levels of 8-hydroxy-2′-deoxyguanosine helps in evaluating oxidative stress and DNA damage in individuals suffering from laryngeal cancer. Hence it serves as a major biomarker of DNA damage, induced by reactive oxygen species (ROS).

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Arif Malik et al.
Drug design, development and therapy, 12, 1431-1443 (2018-06-07)
The present study investigates the hepato- and DNA-protective effects of standardized extracts of Cleome brachycarpa (cabralealactone), Solanum incanum (solasodin), and Salvadora oleioides (salvadorin) in rats. Hepatotoxicity was induced with intraperitoneal injection of carbon tetrachloride (CCl4) (1 mL/kg b.wt.) once a
Aireza Shirpoor et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 84, 698-704 (2016-10-07)
Chronic alcohol ingestion is associated with pronounced detrimental effects on the renal system. In the current study, the protective effect of ginger extract on ethanol-induced damage was evaluated through determining 8-OHdG, cystatin C, glomerular filtration rate, and pathological changes such
Increased blood 8-hydroxy-2-deoxyguanosine levels in methamphetamine users during early abstinence
Huang M C, et al.
The American Journal of Drug and Alcohol Abuse, 44(3), 395-402 (2018)
Elisabeth Müllner et al.
Molecular nutrition & food research, 57(2), 328-338 (2012-11-14)
Type 2 diabetes is a multifactorial disease associated with increased oxidative stress, which may lead to increased DNA damage. The aim of this study was to investigate the effect of a healthy diet on DNA oxidation in diabetics and nondiabetics.
Pan Chen et al.
Life sciences, 232, 116594-116594 (2019-06-25)
Sleep deficiency has been reported to be associated with some oral health problems. Oral ulcers are very common lesions of the oral mucosa, which severely impact patients' quality of life. However, the association between sleep deficiency and the oral ulcer

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