139307-94-1
Chemical Structure
8-Oxo-dGTP
Synonym(s): 8-Oxo-Deoxyguanosine triphosphate
- CAS No.: 139307-94-1
- Formula:C10H16N5O14P3
- Molecular Weight:523.18
IUPAC Name: ((2R,3S,5R)-5-(2-amino-8-hydroxy-6-oxo-1,6-dihydro-9H-purin-9-yl)-3-hydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
InChIKey: BUZOGVVQWCXXDP-VPENINKCSA-N
SMILES: O[C@H]1C[C@H](N2C(N=C(N)NC3=O)=C3N=C2O)O[C@@H]1COP(OP(OP(O)(O)=O)(O)=O)(O)=O
Biological Activity: 8-Oxo-dGTP (8-Oxo-Deoxyguanosine triphosphate) is an oxidized guanine nucleotide formed by ROS-mediated oxidative modification of dGTP, and it also serves as a key substrate for 8-oxo-dGTP pyrophosphohydrolases (such as hMTH1 and E. coli MutT). 8-Oxo-dGTP acts as a DNA mutagen, inserts into nascent DNA and pairs with adenine and cytosine, inducing A:T to C:G transversion mutations. Furthermore, 8-Oxo-dGTP causes oxidative DNA base modification, strand breakage and S-phase arrest, and ultimately triggers AIF-mediated apoptosis and promotes spontaneous carcinogenesis in mth1-deficient mice. Accumulation of 8-Oxo-dGTP in cells induces genomic instability, but it exhibits a tumor-suppressive effect that reduces tumor incidence in mouse models instead. 8-Oxo-dGTP is widely used in studies related to spontaneous carcinogenesis, Parkinson's disease, Alzheimer's disease, heart failure and tumor mechanisms[1][2][3][4].
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8-Oxo-dGTP | 8-Oxo-dGTP (8-Oxo-Deoxyguanosine triphosphate) is an oxidized guanine nucleotide formed by ROS-mediated oxidative modification of dGTP, and it also serves as a key substrate for 8-oxo-dGTP pyrophosphohydrolases (such as hMTH1 and E. coli MutT). 8-Oxo-dGTP acts as a DNA mutagen, inserts into nascent DNA and pairs with adenine and cytosine, inducing A:T to C:G transversion mutations. Furthermore, 8-Oxo-dGTP causes oxidative DNA base modification, strand breakage and S-phase arrest, and ultimately triggers AIF-mediated apoptosis and promotes spontaneous carcinogenesis in mth1-deficient mice. Accumulation of 8-Oxo-dGTP in cells induces genomic instability, but it exhibits a tumor-suppressive effect that reduces tumor incidence in mouse models instead. 8-Oxo-dGTP is widely used in studies related to spontaneous carcinogenesis, Parkinson's disease, Alzheimer's disease, heart failure and tumor mechanisms. | |||||||||||||||||||||
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References
- [1]. Sakai Y, et al. A molecular basis for the selective recognition of 2-hydroxy-dATP and 8-oxo-dGTP by human MTH1. J Biol Chem. 2002;277(10):8579-8587. [Content Brief]
- [2]. Bialkowski K, et al. A novel assay of 8-oxo-2′-deoxyguanosine 5′-triphosphate pyrophosphohydrolase (8-oxo-dGTPase) activity in cultured cells and its use for evaluation of cadmium (II) inhibition of this activity[J]. Nucleic acids research, 1998, 26(13): 3194-3201.
- [3]. Tsutsui H, et al. 8-oxo-dGTPase, which prevents oxidative stress-induced DNA damage, increases in the mitochondria from failing hearts. Circulation. 2001;104(24):2883-2885. [Content Brief]
- [4]. Li J, et al. 8-oxo-dGTP curbs tumor development via S phase arrest and AIF-mediated apoptosis. Free Radic Biol Med. 2023;196:53-64. [Content Brief]
