D5287
2′-Deoxyinosine
≥98%
Synonym(s):
9-(2-Deoxy-β-D-ribofuranosyl)hypoxanthine
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About This Item
Empirical Formula (Hill Notation):
C10H12N4O4
CAS Number:
Molecular Weight:
252.23
UNSPSC Code:
41106305
NACRES:
NA.51
PubChem Substance ID:
EC Number:
212-964-1
Beilstein/REAXYS Number:
33517
MDL number:
Assay:
≥98%
Biological source:
synthetic (organic)
Form:
powder
Solubility:
1 M NH4OH: 50 mg/mL, clear, colorless
Storage temp.:
−20°C
InChI key
VGONTNSXDCQUGY-RRKCRQDMSA-N
InChI
1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1
SMILES string
OC[C@H]1O[C@H](C[C@@H]1O)n2cnc3C(=O)NC=Nc23
biological source
synthetic (organic)
assay
≥98%
form
powder
impurities
inosine, essentially free
solubility
1 M NH4OH: 50 mg/mL, clear, colorless
storage temp.
−20°C
Quality Level
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Application
2′-Deoxyinosine has been used in the quantification of nucleoside forms of DNA lesion in a single DNA sample by liquid chromatography tandem mass spectrometry (LC-MS/MS). It has also been used as a standard for high performance liquid chromatography analysis.
Biochem/physiol Actions
2′-Deoxyinosine is a nucleoside composed of hypoxanthine attached to 2′-deoxyribose via a β-N9-glycosidic bond. 2′-Deoxyinosine in DNA can arise from deamination of adenosine. 2′-deoxyinsine can be used as a model compound to study the chemistry of adduct formation and radical chemistry that may affect DNA structures. 2′-Deoxyinosine is used to produce hybridization-sensitive fluorescent DNA probes with self-avoidance ability.
2′-Deoxyinosine is a nucleoside form of hypoxanthine. It is a DNA damage product resulting from the impairment of DNA by reactive nitrogen species. 2′-deoxyinosine is formed from nitrosative deamination by N2O3.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Shuji Ikeda et al.
Organic & biomolecular chemistry, 8(3), 546-551 (2010-01-22)
Hybridization-sensitive fluorescent probes have an inherent disadvantage: self-dimerization of the probe prevents the fluorescence quenching prior to hybridization with the target, resulting in a high background signal. To avoid self-dimerization of probes, we focused on a base pair formed by
Quantification of DNA damage products resulting from deamination, oxidation and reaction with products of lipid peroxidation by liquid chromatography isotope dilution tandem mass spectrometry
Taghizadeh K, et al.
Nature Protocols, 3(8), 1287-1287 (2008)
Lipid peroxidation dominates the chemistry of DNA adduct formation in a mouse model of inflammation.
Bo Pang et al.
Carcinogenesis, 28(8), 1807-1813 (2007-03-10)
In an effort to define the prevalent DNA damage chemistry-associated chronic inflammation, we have quantified 12 DNA damage products in tissues from the SJL mouse model of nitric oxide (NO) overproduction. Using liquid chromatography-mass spectrometry/MS and immunoblot techniques, we analyzed
Rongjuan Mi et al.
Mutation research, 735(1-2), 12-18 (2012-06-06)
The human endonuclease V gene is located in chromosome 17q25.3 and encodes a 282 amino acid protein that shares about 30% sequence identity with bacterial endonuclease V. This study reports biochemical properties of human endonuclease V with respect to repair
Bernard Weiss
DNA repair, 7(2), 205-212 (2007-11-06)
Deoxyinosine (dI) is produced in DNA by the hydrolytic or nitrosative deamination of deoxyadenosine. It is excised in a repair pathway that is initiated by endonuclease V, the product of the nfi gene. The repair was studied in vivo using
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