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MilliporeSigma

D5287

2′-Deoxyinosine

≥98%

Synonym(s):

9-(2-Deoxy-β-D-ribofuranosyl)hypoxanthine

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D5287-100MG

$59.10

D5287-1G

$282.00

$59.10

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About This Item

Empirical Formula (Hill Notation):
C10H12N4O4
CAS Number:
890-38-0
Molecular Weight:
252.23
Beilstein/REAXYS Number:
33517
EC Number:
212-964-1
MDL number:
MFCD00005762
UNSPSC Code:
41106305
PubChem Substance ID:
24893935
NACRES:
NA.51

Key Documents

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biological source

synthetic (organic)

Quality Level

200

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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This Item
D5412D7400D8668
2′-Deoxyinosine ≥98%

Sigma-Aldrich

D5287

2′-Deoxyinosine

2′-Deoxyuridine ≥98.5%

Sigma-Aldrich

D5412

2′-Deoxyuridine

2′-Deoxyadenosine monohydrate ≥99%

Sigma-Aldrich

D7400

2′-Deoxyadenosine monohydrate

2′-Deoxyadenosine monohydrate powder, BioReagent, suitable for cell culture

Sigma-Aldrich

D8668

2′-Deoxyadenosine monohydrate

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

synthetic (organic)

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

200

assay

≥98%

assay

≥98.5%

assay

≥99%

assay

≥99% (HPLC)

form

powder

form

powder

form

powder

form

powder

solubility

1 M NH4OH: 50 mg/mL, clear, colorless

solubility

water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

water: 25 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

H2O: soluble 25 mg/mL, clear to slightly hazy, colorless to faintly yellow

storage temp.

−20°C

storage temp.

-

storage temp.

2-8°C

storage temp.

2-8°C

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).[1] It has also been used as a standard for high performance liquid chromatography analysis.[2]

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] 2′-deoxyinosine is formed from nitrosative deamination by N2O3.[1]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000370234
0000370218
0000368748
SLCQ4417
0000370234

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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)
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
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
Manabu Yasui et al.
Journal of molecular biology, 377(4), 1015-1023 (2008-02-29)
Chronic inflammation involving constant generation of nitric oxide (*NO) by macrophages has been recognized as a factor related to carcinogenesis. At the site of inflammation, nitrosatively deaminated DNA adducts such as 2'-deoxyinosine (dI) and 2'-deoxyxanthosine are primarily formed by *NO
View All Related Papers

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