8-Hydroxyguanine

CAS: 5614-64-2

Ref. 3D-FH10533

Product Information

• Name: 8-Hydroxyguanine
• Synonyms: 2-Amino-6,8-dihydroxypurine2-Amino-6,8-purinediol2-Amino-7,9-dihydro-1H-purine-6,8-dione8-Oxoguanine, 1H-Purine-6,8-dione, 2-amino-7,9-dihydro-, 2-Amino-6,8-purinediol, 2-Amino-7,9-dihydro-1H-purine-6,8-dione, 2-Amino-8-hydroxy-1H-purin-6(7H)-one, 2-Amino-8-hydroxy-6,9-dihydro-1H-purin-6-one, 2-Aminopurin-6,8-diol, 2-Aminopurina-6,8-Diol, 2-Aminopurine-6,8-Diol, 2-amino-3H-purine-6,8-dione, 2-amino-7,9-dihydro-3H-purine-6,8-dione, 7,8-Dihydro-8-oxoguanine, 8-Oxo-7,8-dihydroguanine, 8-Oxoguanine, Nsc 22720, Purine-6,8(1H,9H)-dione, 2-amino-, Purine-6,8-diol, 2-amino-

Description

8-Hydroxyguanine is a purine derivative that is found in DNA. It is a byproduct of oxidative damage to DNA and can cause mutations. 8-Hydroxyguanine binds to the α1 subunit of DNA polymerase, inhibiting the polymerization of nucleotides. This prevents the synthesis of new DNA, resulting in cell death. In humans, 8-hydroxyguanine appears to be repaired at a higher rate than other organisms such as bacteria. A study has shown that human cells are able to repair 8-hydroxyguanine by using an enzyme called O6-alkylguanine transferase (AGT). The AGT protein removes the alkyl group from the guanine base and replaces it with an amino group during repair. This process results in the formation of O6-methylguanine, which can be eliminated by methylation or excreted through urine.

• Brand: Biosynth

Chemical properties

• Molecular weight: 167.13 g/mol
• Formula: C₅H₅N₅O₂
• Purity: Min. 98 Area-%
• Color/Form: White Powder
• InChI: InChI=1S/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12)
• InChI key: InChIKey=CLGFIVUFZRGQRP-UHFFFAOYSA-N
• SMILES: Nc1nc2[nH]c(=O)[nH]c2c(=O)[nH]1