M2389
N6-Methyl-2′-deoxyadenosine
≥98% (TLC), powder
Synonym(s):
6mdA, N6-Me-dAdo, m6dA
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About This Item
Empirical Formula (Hill Notation):
C11H15N5O3
CAS Number:
Molecular Weight:
265.27
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
MDL number:
Product Name
N6-Methyl-2′-deoxyadenosine,
Quality Level
SMILES string
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
InChI key
DYSDOYRQWBDGQQ-XLPZGREQSA-N
assay
≥98% (TLC)
form
powder
solubility
acetic acid: 49.00-51.00 mg/mL, clear, colorless
storage temp.
−20°C
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.
Biochem/physiol Actions
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.
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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J C Rogers et al.
The Plant journal : for cell and molecular biology, 7(2), 221-233 (1995-02-01)
Methylation of deoxycytosine residues in plant nuclear DNA at CpG dinucleotides is generally assumed to suppress transcription, while deoxyadenosine methylation on recombinant reporter gene constructs transiently introduced into plant cells increases expression by uncharacterized mechanisms. A particle bombardment transient expression
Shengjie Li et al.
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 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
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
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