8-OXO-2'-DEOXYGUANOSINE Chemical Properties

Melting point:

217-220°C

Density 

2.25±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in DMSO (up to 10 mg/ml).

form 

White to off-white solid.

pka

7.86±0.20(Predicted)

color 

Off-white

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.

InChI

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)/t3-,4+,5+/m0/s1

InChIKey

HCAJQHYUCKICQH-VPENINKCSA-N

SMILES

OC[C@H]1O[C@@H](N2C3=C(C(NC(=N3)N)=O)NC2=O)C[C@@H]1O

Safety Information

Safety Statements 

24/25

WGK Germany 

3

RTECS 

MF8782675

HS Code 

29349990

8-OXO-2'-DEOXYGUANOSINE Usage And Synthesis

Description

8-Oxo-2′-deoxyguanosine (88847-89-6) is a useful marker for DNA damage via a variety of oxidative processes.1?It is a critical biomarker for oxidative stress and carcinogenesis.2,3

Chemical Properties

White Crystalline Solid

Uses

A marker compound indicative of DNA damage associated with mutagenesis and carcinogenesis. Can induce differentiation of Friend murine erythroleukemia cells in vitro.

Uses

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

Definition

ChEBI: Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.

Biochem/physiol Actions

A marker compound typically indicative of DNA damage associated with mutagenesis and carcinogenesis

References

[1] K B BECKMAN  B N A. Oxidative decay of DNA.[J]. The Journal of Biological Chemistry, 1997, 272 32: 19633-19636. DOI:10.1074/jbc.272.32.19633
[2] ROBERTA ANDREOLI. 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.[J]. Biomarkers, 2010, 15 3: 221-231. DOI:10.3109/13547500903434501
[3] PAOLA MANINI . Biomarkers of nucleic acid oxidation, polymorphism in, and expression of, hOGG1 gene in styrene-exposed workers[J]. Toxicology letters, 2009, 190 1: Pages 41-47. DOI:10.1016/j.toxlet.2009.06.862

8-OXO-2'-DEOXYGUANOSINE(88847-89-6)Related Product Information

• 8-OXO-2'-DEOXYGUANOSINE
• Loxoribine
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• Guanine
• Purine
• 7-propyl-8-oxoguanosine
• 8-HYDROXYGUANOSINE
• 5'-O-(4,4'-DIMETHOXYTRITYL)-N2-ISOBUTYRYL-8-OXO-2'-DEOXYGUANOSINE, 3'-[(2-CYANOETHYL)-(N,N-DIISOPROPYL)]PHOSPHORAMIDITE
• 8-ALLYLOXY-3'-O-[(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINO]-5'-O-(4,4'-DIMETHOXYTRITYL)-N2-[(DIMETHYLAMINO)METHYLIDINE]-2'-DEOXYGUANOSINE
• 8-ALLYLOXY-N2-ISOBUTYRYL-2'-DEOXYGUANOSINE
• 8-ALLYLOXY-2'-DEOXYGUANOSINE
• Tri-O-acetyl-8-(allyloxy)guanosine
• 5'-O-(DIMETHOXYTRITYL)-8-HYDROXY-N2-ISOBUTRYL-2'-DEOXYGUANOSINE
• 8-BENZYLOXY-N2-ISOBUTYRYL-2'-DEOXYGUANOSINE
• 8-HYDROXY-N2-ISOBUTRYL-2'-DEOXYGUANOSINE
• 8-ALLYLOXY-N2-(DMF)-2'-DEOXYGUANOSINE
• 8-Benzyloxy-2'-deoxy-D-guanosine
• 8-(Allyloxy)guanosine