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M2389

Sigma-Aldrich

N6-Methyl-2′-deoxyadenosine

Synonyme(s) :

6mdA, N6-Me-dAdo, m6dA

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About This Item

Formule empirique (notation de Hill):
C11H15N5O3
Numéro CAS:
2002-35-9
Poids moléculaire :
265.27
Numéro MDL:
MFCD00055999
Code UNSPSC :
41106305
ID de substance PubChem :
24896727
Nomenclature NACRES :
NA.51

Pureté

≥98% (TLC)

Niveau de qualité

200

Forme

powder

Solubilité

acetic acid: 49.00-51.00 mg/mL, clear, colorless

Température de stockage

−20°C

Chaîne SMILES 

CNc1ncnc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO)O3

InChI

1S/C11H15N5O3/c1-12-10-9-11(14-4-13-10)16(5-15-9)8-2-6(18)7(3-17)19-8/h4-8,17-18H,2-3H2,1H3,(H,12,13,14)/t6-,7+,8+/m0/s1

Clé InChI

DYSDOYRQWBDGQQ-XLPZGREQSA-N

Application

N6-Methyl-2′-deoxyadenosine has been used as a standard to assess the levels of modified bases in genomic DNA by the ultra-high-performance liquid chromatography coupled with triple quadrupole mass spectrometry (UHPLC-QQQ-MS/MS) method. It has also been used to study its potential in promoting the proliferation oferythroid progenitor cells.

Actions biochimiques/physiologiques

N6-Methyl-2′-deoxyadenosine (N6-Me-dAdo) is a precursor of N6-methyl 2′-deoxyadenosine 3′,5′-bisphosphate (N6MABP), a competitive and selective inhibitor of P2Y1 receptors. It is located at the transcription start site and plays a role in increased gene expression in Chlamydomonas reindardtii. N6-Me-dAdo augments the within transposable elements and is present at higher levels during the development of Drosophila. It is involved in the regulation of gene transcription, DNA repair, and replication in prokaryotes and protists. N6-Me-dAdo complemented with gene bodies might induce gene expression in human cells.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Frontiers in microbiology, 10, 1905-1905 (2019-09-10)
DNA methylation serves as a vital component of restriction-modification (R-M) systems in bacteria, where it plays a crucial role in defense against foreign DNA. Recent studies revealed that DNA methylation has a global impact on gene expression. Deinococcus radiodurans, an
J J Solomon et al.
Chemico-biological interactions, 51(2), 167-190 (1984-09-15)
Reaction of the rodent carcinogen acrylonitrile (AN) at pH 5.0 and/or pH 7.0 for 10 and/or 40 days with 2'-deoxyadenosine (dAdo), 2'-deoxycytidine (dCyd), 2'-deoxyguanosine (dGuo), 2'-deoxyinosine (dIno), N6-methyl-2'-deoxyadenosine (N6-Me-dAdo) and thymidine (dThd) resulted in the formation of cyanoethyl and carboxyethyl
J L Boyer et al.
British journal of pharmacology, 124(1), 1-3 (1998-06-18)
The antagonist activity of N6-methyl 2'-deoxyadenosine 3',5'-bisphosphate (N6MABP) has been examined at the phospholipase C-coupled P2Y1 receptor of turkey erythrocyte membranes. N6MABP antagonized 2MeSATP-stimulated inositol phosphate hydrolysis with a potency approximately 20 fold greater than the previously studied parent molecule
Mariangela Chisari et al.
Molecular neurobiology, 54(6), 4081-4093 (2016-06-20)
Astrocytes regulate neuronal activity and blood brain barrier through tiny plasma membrane branches or astrocytic processes (APs) making contact with synapses and brain vessels. Several transmitters released by astrocytes and exerting their action on several receptor classes expressed by astrocytes
Determination of DNA adenine methylation in genomes of mammals and plants by liquid chromatography/mass spectrometry
Huang W, et al.
Royal Society of Chemistry Advances, 5(79), 64046-64054 (2015)
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