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About This Item
Empirical Formula (Hill Notation):
C5H5N5
CAS Number:
Molecular Weight:
135.13
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
207-197-4
MDL number:
Product Name
2-Aminopurine, ≥99%
InChI
1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)
InChI key
MWBWWFOAEOYUST-UHFFFAOYSA-N
SMILES string
Nc1ncc2[nH]cnc2n1
biological source
synthetic
assay
≥99%
form
powder
mp
280-282 °C (lit.)
storage temp.
2-8°C
Quality Level
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Application
2-Aminopurine (2-AP) is used to specifically inhibit double-stranded RNA-dependent protein kinase, protein kinase R (PKR).
2-Aminopurine has been used to inhibit eukaryotic initiation factor-2α (eIF2α)-phosphorylation of osteoarthritis (OA) chondrocytes.
Biochem/physiol Actions
2-Aminopurine (2AP) is an analog of guanosine and adenosine, which can base pair with cytosine and thymine. It is used as a fluorescent probe in nucleic acid structure and dynamics. 2-Aminopurine (2-AP) inhibits double-stranded RNA-dependent protein kinase, protein kinase R (PKR).
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Julien Godet et al.
Nucleic acids research, 41(9), 5036-5048 (2013-03-21)
The HIV-1 nucleocapsid protein (NCp7) is a nucleic acid chaperone required during reverse transcription. During the first strand transfer, NCp7 is thought to destabilize cTAR, the (-)DNA copy of the TAR RNA hairpin, and subsequently direct the TAR/cTAR annealing through
2-Aminopurine.
A Ronen
Mutation research, 75(1), 1-47 (1980-01-01)
Endoplasmic reticulum stress induces the expression of COX-2 through activation of eIF2alpha, p38-MAPK and NF-kappaB in advanced glycation end products stimulated human chondrocytes
Rasheed Z and HaqqiTM
Biochimica et Biophysica Acta - Molecular Cell Research, 1823(12), 2179-2189 (2012)
Bakhos A Tannous et al.
Journal of the National Cancer Institute, 105(17), 1322-1331 (2013-08-14)
Glioblastomas exhibit a high level of chemotherapeutic resistance, including to the antimitotic agents vincristine and taxol. During the mitotic agent-induced arrest, glioblastoma cells are able to perform damage-control and self-repair to continue proliferation. Monopolar spindle 1 (MPS1/TTK) is a checkpoint
Double-Stranded RNA-Dependent Protein Kinase Is Involved in 2-Methoxyestradiol?Mediated Cell Death of Osteosarcoma Cells
Shogren KL, et al.
Journal of Bone and Mineral Research, 22(1), 29-36 (2007)
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