8-Oxo-2’-deoxyguanosine

• CAT Number: R003400
• CAS Number: 88847-89-6
• Molecular Formula: C10H13N5O5
• Molecular Weight: 283.244
• Purity: ≥95%
• Storage: Room temperature
• IUPAC Name: 2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,7-dihydropurine-6,8-dione
• 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: C1C(C(OC1N2C3=C(C(=O)N=C(N3)N)NC2=O)CO)O

​8-Hydroxy-<wbr />2'-deoxyguanosine(cas 88847-89-6) is produced by oxidative damage of DNA by reactive oxygen and nitrogen species, including hydroxyl radical and peroxynitrite. It serves as a measure of oxidative stress in biological systems.

Reference

1. Org Biomol Chem. 2016 Aug 16;14(33):7949-55. doi: 10.1039/c6ob01485b.
Synthetic receptor molecules for selective fluorescence detection of 8-oxo-dGTP in aqueous media.
Fuchi Y(1), Fukuda T(1), Sasaki S(1).
Author information:
(1)Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan. .
A series of 9-hydroxy-1,3-diazaphenoxazine-2-one derivatives were synthesized as fluorescent receptor molecules for 8-oxo-dGTP, which attach the cyclen-zinc complex at the 3-N position as the binding site for the triphosphate and the (2-aryloxycarbonylamino)ethyl group at the 9-O position as the hydrogen bonding site for 8-oxoguanine. Among these molecules, the receptor molecule 5a-Zn constructed of the ethyl linker at 3-N and the (2-benzyloxycarbonyl amino)ethyl group at 9-O displayed the best recognition ability for 8-oxoguanosine triphosphate (8-oxo-dGTP) in aqueous media. The receptor 5a-Zn was also shown to selectively detect 8-oxo-dGTP in a cell lysate solution.

2. Bioorg Med Chem Lett. 2000 Aug 7;10(15):1677-9.
Efficient synthesis of 8-oxo-dGTP: a mutagenic nucleotide.
Nampalli S(1), Kumar S.
Author information:
(1)Amersham Pharmacia Biotech, Piscataway, NJ 08855, USA. An efficient synthesis of mutagenic and oxidative DNA damage product, 8-oxo-dGTP (4) has been achieved in high yield, along with a serendipitous generation of 8-dimsyl-dG (2). In combination with dPTP (5), 8-oxo-dGTP (4) can be formulated into a kit for investigating DNA random mutagenesis.

3. J Biol Chem. 1993 Nov 5;268(31):23524-30.
Cloning and expression of cDNA for a human enzyme that hydrolyzes 8-oxo-dGTP, a mutagenic substrate for DNA synthesis.
Sakumi K(1), Furuichi M, Tsuzuki T, Kakuma T, Kawabata S, Maki H, Sekiguchi M.
Author information:
(1)Medical Institute of Bioregulation, Faculty of Science, Kyushu University, Fukuoka, Japan.
8-Oxoguanine (8-oxo-7, 8-dihydroguanine) is produced in DNA, as well as in nucleotide pools of cells, by active oxygen species normally formed during cellular metabolic processes. 8-Oxoguanine nucleotide can pair with cytosine and adenine nucleotides at almost equal efficiencies, and transversion mutation ensues. Human cells contain enzyme activity, which hydrolyzes 8-oxo-dGTP to 8-oxo-dGMP, and this enzyme is responsible for preventing misincorporation of 8-oxoguanine into DNA. We purified this particular human enzyme to physical homogeneity and determined a partial amino acid sequence. We then cloned the cDNA for human 8-oxo-dGTPase and examined its nucleotide sequence. The human protein comprises 156 amino acid residues and has some sequence homology with the Escherichia coli MutT protein, which has a distinct 8-oxo-dGTPase activity. When the human cDNA was expressed in E. coli mutT- mutant cells, there was a significant amount of 8-oxo-dGTPase activity. In such cells, the frequency of spontaneous mutation was greatly reduced. We propose that the human 8-oxo-dGTPase protects genetic information from the untoward effects of endogenous oxygen radicals.