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D5287

Sigma-Aldrich

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:
890-38-0
Molecular Weight:
252.23
Beilstein:
33517
EC Number:
212-964-1
MDL number:
MFCD00005762
UNSPSC Code:
41106305
PubChem Substance ID:
24893935
NACRES:
NA.51

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

SMILES string

OC[C@H]1O[C@H](C[C@@H]1O)n2cnc3C(=O)NC=Nc23

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

InChI key

VGONTNSXDCQUGY-RRKCRQDMSA-N

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
Chia-Chia Lee et al.
DNA repair, 9(10), 1073-1079 (2010-08-11)
Deoxyinosine (dI) in DNA can arise from hydrolytic or nitrosative deamination of deoxyadenosine. It is excised in a repair pathway that is initiated by endonuclease V, the nfi gene product, in Escherichia coli. Repair was studied in vitro using M13mp18
Min Dong et al.
Chemical research in toxicology, 19(1), 50-57 (2006-01-18)
Nitric oxide (NO) is a physiologically important molecule that has been implicated in the pathophysiology of diseases associated with chronic inflammation, such as cancer. While the complicated chemistry of NO-mediated genotoxicity has been extensively study in vitro, neither the spectrum
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