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8-Oxo-dG

Alias: 8 Oxo dG; 8-OHdG; 88847-89-6; 8-Hydroxy-2'-deoxyguanosine; 8-Oxo-2'-deoxyguanosine; 8-Oxo-dG; 8-Hydroxydeoxyguanosine; 8-Oxo-7,8-dihydro-2'-deoxyguanosine; 2'-deoxy-8-oxoguanosine; 8-Oxo-7-hydrodeoxyguanosine; 8 OHdG; 8-Oxo-dG
Cat No.:V6418 Purity: ≥98%
8-Hydroxy-2'-deoxyguanosine is a key biomarker of oxidative stress and carcinogenesis.
8-Oxo-dG
8-Oxo-dG Chemical Structure CAS No.: 88847-89-6
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of 8-Oxo-dG:

  • 8-Hydroxy-2'-deoxyguanosine-15N5
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
8-Hydroxy-2'-deoxyguanosine is a key biomarker of oxidative stress and carcinogenesis.
Biological Activity I Assay Protocols (From Reference)
Targets
Endogenous Metabolite
ln Vitro
8-Hydroxy-2'-deoxyguanosine (8-OHdG) is a useful biomarker for determining the risk of developing several types of cancer and degenerative illnesses. The biomarker 8-hydroxy-2'-deoxyguanosine (8-OHdG), also known as 8-oxodG, is involved in the start and progression of carcinogenesis and has emerged as a critical marker for assessing the consequences of endogenous oxidative damage to DNA. After exposure to carcinogens such tobacco smoke, asbestos fibers, heavy metals, and polycyclic aromatic hydrocarbons, this biomarker has been used to evaluate DNA damage in humans [1].
Enzyme Assay
There is extensive experimental evidence that oxidative damage permanently occurs to lipids of cellular membranes, proteins, and DNA. In nuclear and mitochondrial DNA, 8-hydroxy-2' -deoxyguanosine (8-OHdG) or 8-oxo-7,8-dihydro-2' -deoxyguanosine (8-oxodG) is one of the predominant forms of free radical-induced oxidative lesions, and has therefore been widely used as a biomarker for oxidative stress and carcinogenesis. Studies showed that urinary 8-OHdG is a good biomarker for risk assessment of various cancers and degenerative diseases. The most widely used method of quantitative analysis is high-performance liquid chromatography (HPLC) with electrochemical detection (EC), gas chromatography-mass spectrometry (GC-MS), and HPLC tandem mass spectrometry. In order to resolve the methodological problems encountered in measuring quantitatively 8-OHdG, the European Standards Committee for Oxidative DNA Damage was set up in 1997 to resolve the artifactual oxidation problems during the procedures of isolation and purification of oxidative DNA products. The biomarker 8-OHdG or 8-oxodG has been a pivotal marker for measuring the effect of endogenous oxidative damage to DNA and as a factor of initiation and promotion of carcinogenesis. The biomarker has been used to estimate the DNA damage in humans after exposure to cancer-causing agents, such as tobacco smoke, asbestos fibers, heavy metals, and polycyclic aromatic hydrocarbons. In recent years, 8-OHdG has been used widely in many studies not only as a biomarker for the measurement of endogenous oxidative DNA damage but also as a risk factor for many diseases including cancer [1].
Toxicity/Toxicokinetics
Toxicity Overview
Uremic toxins, such as 8-hydroxy-2X-deoxyguanosine, can be actively transported to the kidneys via organic ion transporters, particularly OAT3. Elevated uremic toxin levels can stimulate the production of reactive oxygen species (ROS). This appears to be mediated by the direct binding of uremic toxins to or inhibition of NADPH oxidases, particularly NOX4, which is abundant in the kidneys and heart (A7868). ROS can induce a variety of different DNA methyltransferases (DNMTs) involved in the silencing of the KLOTHO protein. KLOTHO has been shown to play an important role in anti-aging, mineral metabolism, and vitamin D metabolism. Multiple studies have shown that in acute or chronic kidney disease, KLOTHO mRNA and protein levels are decreased due to elevated local ROS levels (A7869).
References

[1]. 8-hydroxy-2' -deoxyguanosine (8-OHdG): A critical biomarker of oxidative stress and carcinogenesis. J Environ Sci Health C Environ Carcinog Ecotoxicol Rev. 2009 Apr;27(2):120-39.

Additional Infomation
8-Hydroxy-2'-deoxyguanosine (8-DG) is a compound in which the 8-position of guanosine is replaced by a hydroxyl group. It is used as a biomarker for oxidative DNA damage. The presence of 8-DG in Vibrio harveyi has been reported, and relevant data are available. 8-DG is the main spontaneous oxidation derivative of 2'-deoxyguanosine and is also a biomarker for oxidative DNA damage. 8-Hydroxy-2'-deoxyguanosine (8-oxo-dG) is generated by the reaction of guanine with reactive oxygen species. Although 8-oxo-dG is usually repaired and cleared by base excision repair mechanisms, it can also mismatch with deoxyadenine, leading to G-to-T transversion mutations, which in turn cause frequent recombinations and single nucleotide polymorphisms (SNPs) in the human genome. The intracellular concentration of 8-Hydroxyguanosine (8-oxo-dG) is an indicator of oxidative stress and can therefore be used to assess the degree of physiological and environmental DNA damage. 8-Oxo-dG is a common oxidized form of deoxyguanosine, in which the C-8 position of the guanine base contains a carbonyl group. 8-Hydroxyguanosine is a uremic toxin. Based on their chemical and physical properties, uremic toxins can be divided into three main categories: 1) small molecule, water-soluble, non-protein-bound compounds, such as urea; 2) small molecule, lipid-soluble and/or protein-bound compounds, such as phenols; 3) larger so-called medium-molecules, such as β2-microglobulin. Long-term exposure to uremic toxins can lead to various diseases, including kidney damage, chronic kidney disease, and cardiovascular disease. 8-Hydroxyguanosine (8-OHdG) is a sensitive marker of DNA damage caused by hydroxyl radicals attacking the guanine C8 site. If this damage is not repaired, it is considered to be associated with mutagenicity and cancer development. 8-OHdG is a common oxidized form of deoxyguanosine, in which the C-8 position of the guanine base contains a carbonyl group.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Exact Mass
283.091
Elemental Analysis
C, 42.41; H, 4.63; N, 24.73; O, 28.24
CAS #
88847-89-6
Related CAS #
8-Hydroxy-2'-deoxyguanosine-15N5;569649-11-2
PubChem CID
135440064
Appearance
White to off-white solid powder
Density
2.3±0.1 g/cm3
Melting Point
217-220ºC
Index of Refraction
1.955
LogP
-1.32
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
2
Heavy Atom Count
20
Complexity
544
Defined Atom Stereocenter Count
3
SMILES
C1[C@@H]([C@H](O[C@H]1N2C3=C(C(=O)NC(=N3)N)NC2=O)CO)O
InChi Key
HCAJQHYUCKICQH-VPENINKCSA-N
InChi Code
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
Chemical Name
2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,7-dihydropurine-6,8-dione
Synonyms
8 Oxo dG; 8-OHdG; 88847-89-6; 8-Hydroxy-2'-deoxyguanosine; 8-Oxo-2'-deoxyguanosine; 8-Oxo-dG; 8-Hydroxydeoxyguanosine; 8-Oxo-7,8-dihydro-2'-deoxyguanosine; 2'-deoxy-8-oxoguanosine; 8-Oxo-7-hydrodeoxyguanosine; 8 OHdG; 8-Oxo-dG
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~155 mg/mL (~547.24 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.58 mg/mL (9.11 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.58 mg/mL (9.11 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.58 mg/mL (9.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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