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N3289

Sigma-Aldrich

N2-Ethyl-2′-deoxyguanosine

≥98% (HPLC), solid

Synonym(s):

N2-Et-dG

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About This Item

Empirical Formula (Hill Notation):
C12H17N5O4
CAS Number:
101803-03-6
Molecular Weight:
295.29
MDL number:
MFCD01631004
UNSPSC Code:
12352200
PubChem Substance ID:
329818605
NACRES:
NA.77

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

H2O: >5 mg/mL

storage temp.

2-8°C

SMILES string

CCNC1=Nc2c(ncn2[C@H]3C[C@H](O)[C@@H](CO)O3)C(=O)N1

InChI

1S/C12H17N5O4/c1-2-13-12-15-10-9(11(20)16-12)14-5-17(10)8-3-6(19)7(4-18)21-8/h5-8,18-19H,2-4H2,1H3,(H2,13,15,16,20)/t6-,7+,8+/m0/s1

InChI key

VOKQFDULHQUWAV-XLPZGREQSA-N

General description

N2-Et-dG, an adduct between DNA and the first metabolite of ethanol (acetaldehyde), strongly blocks transcription by RNA polymerases (RNAPs), including mammalian RNAPII and yeast RNAPII, E. coli RNAP, as well as T7 RNAP. All three of the multisubunit RNAPs incorporate a single rNTP residue opposite the N2-Et-dG lesion. The mammalian RNAPII exclusively incorporates cytidine monophosphate (CMP) opposite the N2-Et-dG lesion. The accessory transcription factor TFIIS does not usually act as a lesion bypass factor; instead, it stimulates the polymerase to remove the CMP incorporated opposite the lesion by mammalian RNAPII. N2-Et-dG reduces CTP incorporation by ~1500 fold.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Carc. 2 - STOT RE 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Liang Qi et al.
Talanta, 209, 120523-120523 (2020-01-02)
DNA adducts usually occur at a level of 0.1-1 adducts per 108 unmodified DNA bases, which can cause many adverse health effects if not normally repaired. Using microgram amounts of DNA to detect DNA adducts remains challenging due to the
Yuan-Jhe Chang et al.
Archives of toxicology, 92(8), 2665-2680 (2018-06-27)
Adductomics is expected to be useful in the characterization of the exposome, which is a new paradigm for studying the sum of environmental causes of diseases. DNA adductomics is emerging as a powerful method for detecting DNA adducts, but reliable

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