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Key Documents

A3509

Sigma-Aldrich

2-Aminopurine

≥99%

Synonym(s):

2-AP

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About This Item

Empirical Formula (Hill Notation):
C5H5N5
CAS Number:
Molecular Weight:
135.13
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic

Quality Level

Assay

≥99%

form

powder

mp

280-282 °C (lit.)

storage temp.

2-8°C

SMILES string

Nc1ncc2[nH]cnc2n1

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

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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).

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
2-Aminopurine fluorescence quenching and lifetimes: role of base stacking
Jean JM and Hall KB
Proceedings of the National Academy of Sciences of the USA, 98(1), 37-41 (2001)
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

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