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H5653

Sigma-Aldrich

8-Hydroxy-2′-deoxyguanosine

≥98% (TLC), DNA damage biomaker

Synonym(s):

8-Oxo-7,8-dihydro-2′-deoxyguanosine, 8-Oxo-dG

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O5
CAS Number:
88847-89-6
Molecular Weight:
283.24
MDL number:
MFCD00210311
UNSPSC Code:
12352200
PubChem Substance ID:
24895702
NACRES:
NA.77

product name

8-Hydroxy-2′-deoxyguanosine, ≥98% (TLC)

Quality Level

200

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).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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.
Rachel Yong et al.
PloS one, 8(8), e73428-e73428 (2013-08-31)
NADPH oxidase 4 (Nox4) is reported to be the major source of reactive oxygen species (ROS) in the kidneys during the early stages of diabetic nephropathy. It has been shown to mediate TGFβ1-induced differentiation of cardiac fibroblasts into myofibroblasts. Despite
Effects of the Phosphodiesterase-5 (PDE-5) Inhibitors, Avanafil and Zaprinast, on Bone Remodeling and Oxidative Damage in a Rat Model of Glucocorticoid-Induced Osteoporosis
Huyut Z, et al.
Medical Science Monitor Basic Research, 24(1), 47-47 (2018)
Liang Cui et al.
Chemical research in toxicology, 26(2), 195-202 (2012-11-13)
Oxidative damage to DNA has many origins, including irradiation, inflammation, and oxidative stress, but the chemistries are not the same. The most oxidizable base in DNA is 2-deoxyguanosine (dG), and the primary oxidation products are 8-oxodG and 2-amino-imidazolone. The latter
Measuring oxidative DNA damage with 8-hydroxy-2?-deoxyguanosine levels in patients with laryngeal cancer
Mazlumoglu M R, et al.
The Annals of Otology, Rhinology, and Laryngology, 126(2), 103-109 (2017)
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