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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 Code

11 - Combustible Solids

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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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
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.
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
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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