D7145
2′-Deoxyguanosine monohydrate
99-100%, synthetic (organic), powder
Synonym(s):
2′-Deoxyguanosine hydrate, 9-(2-Deoxy-β-D-ribofuranosyl)guanine, Guanine-2′-deoxyriboside
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About This Item
Empirical Formula (Hill Notation):
C10H13N5O4 · H2O
CAS Number:
Molecular Weight:
285.26
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
MDL number:
Beilstein/REAXYS Number:
39814
Assay:
99-100%
Biological source:
synthetic (organic)
Form:
powder
Solubility:
1 M NH4OH: 50 mg/mL, clear, colorless
Product Name
2′-Deoxyguanosine monohydrate, 99-100%
InChI
1S/C10H13N5O4.H2O/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6;/h3-6,16-17H,1-2H2,(H3,11,13,14,18);1H2/t4-,5+,6+;/m0./s1
SMILES string
O.NC1=Nc2c(ncn2[C@H]3C[C@H](O)[C@@H](CO)O3)C(=O)N1
InChI key
LZSCQUCOIRGCEJ-FPKZOZHISA-N
biological source
synthetic (organic)
assay
99-100%
form
powder
solubility
1 M NH4OH: 50 mg/mL, clear, colorless
Quality Level
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Application
2′-Deoxyguanosine monohydrate has been used as a nucleoside supplement:
- to study its effect on mitochondrial DNA copy number in deoxyguanosine kinase (dguok) mutant zebrafish,
- in tissue culture medium for deoxyribonucleotide triphosphate (dNTP) synthesis,
- in RPMI (Roswell Park Memorial Institute)-1640 medium to eliminate the endogenous thymocytes
Biochem/physiol Actions
Deoxyguanosine (dG) is a purine nucleoside that upon sequential phosphorylation (kinases) forms deoxyguanosine triphosphate (dGTP) which is used by DNA polymerases and reverse transcriptases to synthesize DNA(s). Deoxyguanosine is the most electron-rich of the four canonical bases and includes many nucleophilic sites which are susceptible to oxidative damage. This makes deoxyguanosine and its oxidized derivatives useful reagents to study mechanisms of oxidative damage to nucleosides and nucleotides.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Zimu Deng et al.
Methods in molecular biology (Clifton, N.J.), 1323, 151-158 (2015-08-22)
Reconstituted thymus organ culture is based on fetal thymus organ culture (FTOC). Purified thymocyte populations, from genetically modified mice or even from other species, are cultured in vitro with thymic lobes depleted of their endogenous thymocytes (by 2'-deoxyguanosine treatment) to
Athanasios Valavanidis et al.
Free radical research, 39(10), 1071-1081 (2005-11-22)
An association between exposure to ambient particulate matter (PM) and increased incidence of mortality and morbidity due to lung cancer and cardiovascular diseases has been demonstrated by recent epidemiological studies. Reactive oxygen species (ROS), especially hydroxyl radicals, generated by PM
Aaron M Fleming et al.
Organic & biomolecular chemistry, 15(39), 8341-8353 (2017-09-25)
In DNA, 2'-deoxyguanosine (dG) is susceptible to oxidative modification by reactive oxygen species (ROS) yielding many products, one of which is 8-oxo-7,8-dihydro-2'-deoxyguanosine (dOG). Interestingly, dOG is stable but much more labile toward oxidation than dG, furnishing 5-guanidinohydantoin-2'-deoxyribose (dGh) that is
Takeji Takamura-Enya et al.
Bioorganic & medicinal chemistry letters, 21(14), 4206-4209 (2011-06-21)
BODIPY-modified 2'-deoxyguanosine was synthesized for use as a detection reagent for genotoxic compounds. BODIPY-FL is a well known fluorescence reagent whose fluorescent light emission diminishes near a guanine base by a photo-induced electron transfer process. We attached BODIPY-Fl to the
Kasper Broedbaek et al.
Free radical biology & medicine, 51(8), 1473-1479 (2011-08-09)
The increasing prevalence of diabetes together with the associated morbidity and mortality calls for additional preventive and therapeutic strategies. New biomarkers that can be used in therapy control and risk stratification as alternatives to current methods are needed and can
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