3868-31-3

Basic information

• Product Name: 8-HYDROXYGUANOSINE
• Synonyms: 2-amino-9-beta-d-ribofuranosylpurine-6,8(1h,9h)-dione;7,8-dihydro-8-oxo-guanosin;9h)-dione,2-amino-9-beta-d-ribofuranosyl-purine-8(1h;8-HYDROXYGUANOSINE;8-OHG;8-OH-GUO;8-OXO-G;8-OXOGUANOSINE
• CAS NO: 3868-31-3
• Molecular Formula: C₁₀H₁₃N₅O₆
• Molecular Weight: 299.24
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Labeling and Diagnostics Reagents;Nucleotides;Carbohydrates & Derivatives;Metabolites & Impurities
• Mol File: 3868-31-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 232-235°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 2.43g/cm³
• Refractive Index: 2.007
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated) Water (Slightly, Heated,
• PKA: 7.75±0.20(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 8-HYDROXYGUANOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-HYDROXYGUANOSINE(3868-31-3)
• EPA Substance Registry System: 8-HYDROXYGUANOSINE(3868-31-3)

Safety Data

• Hazardous Substances Data: 3868-31-3(Hazardous Substances Data)

Usage

Description

8-HYDROXYGUANOSINE, also known as 8-oxo-7,8-dihydroguanosine, is a nucleoside derived from the oxidation of guanosine (G). It is a crystalline solid and is considered a marker of oxidative stress in cells. The presence of 8-HYDROXYGUANOSINE is indicative of DNA damage associated with mutagenesis and carcinogenesis.

Uses

Used in Research and Diagnostics:
8-HYDROXYGUANOSINE is used as a biomarker for [detecting oxidative stress and DNA damage] in cells. Its presence indicates [the potential for mutagenesis and carcinogenesis], making it a valuable tool in [cancer research and diagnostics].
Used in Pharmaceutical Applications:
8-HYDROXYGUANOSINE is used as an inducer of differentiation for [Friend murine erythroleukemia cells in vitro]. This application is significant in [studying the mechanisms of cell differentiation and potential therapeutic approaches for leukemia].
Used in Antioxidant and Stress Response Studies:
8-HYDROXYGUANOSINE is used as a research compound to investigate [the effects of oxidative stress on cellular processes] and to develop [antioxidant strategies to mitigate DNA damage and associated health risks].
Used in Chemical and Material Science:
As a crystalline solid, 8-HYDROXYGUANOSINE can be used in [the development of novel materials with potential applications in various industries], such as [pharmaceuticals, cosmetics, or environmental monitoring].

Safety Profile

Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C10H13N5O6/c11-9-13-6-3(7(19)14-9)12-10(20)15(6)8-5(18)4(17)2(1-16)21-8/h2,4-5,8,16-18H,1H2,(H,12,20)(H3,11,13,14,19)

Upstream product

• 961-07-9 2'-Deoxyguanosine 
• 118-00-3 G 
• 88847-89-6 7,8-dihydro-8-oxo-2'-deoxyguanosine 
• 104826-07-5 N⁷-aminoguanosine 

Relevant articles and documents

High Activity of an Fe-tfda (tfda = 2-aminomethyltetrahydrofuran-N,N-diacetic acid) Complex for Hydroxylation at the Aromatic and Alkane Rings of 2'-Deoxyguanosine in the Presence of Hydrogen Peroxide

An iron(III) complex with tfda (2-aminomethyltetrahydrofuran-N,N-diacetic acid) exhibits high activity for hydroxylation at the 8 and 2' positions of deoxyguanosine in the presence of hydrogen peroxide; this demonstrates that a facile transformation from deoxyribonucleotide to ribonucleotide in vivo may be possible.

Formation and reactions of N7-aminoguanosine and derivatives

Arylamines are mutagens and carcinogens and are thought to initiate tumors by forming adducts with DNA. The major adducts are C8-guanyl, and we have previously suggested a role for guanyl-N7 intermediates in the formation process. N7-Aminoguanosine (Guo) was synthesized and characterized, with the position of the NH2 at N7 established by two- dimensional rotating frame Overhauser enhancement NMR spectroscopy. In DMF, N7-NH2Guo formed C8-NH2Guo and the cyclic product C8:5'-O-cycloGuo. In aqueous media, these products were formed along with 8-oxo-7,8-dihydroGuo, N7-NH2guanine, and a product characterized as a purine 8,9-ring-opened derivative (N-aminoformamidopyrimidine). The rate of aqueous decomposition of N7-NH2Guo increased with pH, with a t( 1/2 ) of 10 h at pH 7 and a t( 1/2 ) of 2 h at pH 9. The rate of migration of NH2 from N7 to C8 is fast enough to explain the formation of C8-NH2Guo from the reaction of 2,4- dinitrophenoxyamine with Guo but not the formation of C8-(arylamino)Guo in the reaction of Guo with aryl hydroxylamine esters; however, the fluorenyl moiety may facilitate the proposed rearrangement by stabilizing an incipient negative charge in the transfer. In the reaction of Guo with N-hydroxy-2- aminofluorene and acetylsalicylic acid, a peak with the mass spectrum expected for N7-(2-aminofluorenyl)Guo was detected early in the reaction and was distinguished from C8-(2-aminofluorenyl)Guo. NMR experiments with [8- 13C]Guo also provided some additional support for transient formation of N7-(2-aminofluorenyl)Guo. We conclude that a guanyl-N7 intermediate is reasonable in the reaction of activated arylamines with nucleic acids, although an exact rate of transfer of an N7-arylamine group to the C8 position has not yet been quantified. The results provide an explanation for the numerous products associated with modification of DNA by activated arylamines. However, the contribution of 'direct' reaction at the guanine C8 atom cannot be excluded.