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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)

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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
2-Aminopurine.
A Ronen
Mutation research, 75(1), 1-47 (1980-01-01)
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
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)
Eda Aydindogan et al.
Biosensors, 9(4) (2019-10-05)
Aptamer-based point-of-care (POC) diagnostics platforms may be of substantial benefit in forensic analysis as they provide rapid, sensitive, user-friendly, and selective analysis tools for detection. Aptasensors have not yet been adapted commercially. However, the significance of the applications of aptasensors

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