A fluorescent analog of guanosine and adenosine
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2-Aminopurine (hydrochloride)

Item No. 18609

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9H-purin-2-amine, dihydrochloride
CAS Number
1428126-74-2
Synonyms
  • 2-AP
Molecular Formula
C5H5N5 • 2HCl
Formula Weight
208.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 5 mg/ml
λmax
216, 305 nm
SMILES
NC1=NC2=NC=NC2=CN1.Cl.Cl
InChi Code
InChI=1S/C5H5N5.2ClH/c6-5-7-1-3-4(10-5)9-2-8-3;;/h1-2H,(H3,6,7,8,9,10);2*1H
InChi Key
ZMYNIVFDDGHSJU-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    50 mg

    $49

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    100 mg

    $93

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    250 mg

    $190

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    500 mg

    $329

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    Product Description

    2-Aminopurine is a fluorescent analog of guanosine and adenosine that is used as a site-specific probe of nucleic acid structure and dynamics.1 It base pairs with cytosine in a wobble configuration or with thymine in a Watson–Crick geometry.1 In addition to its usefulness in studies of base stacking interactions, 2-aminopurine has been used as a probe for DNA base flipping by methyl transferases.2 2-Aminopurine exhibits an excitation/emission of 320/381 nm, respectively, when adjusted to reduce interference with DNA base absorption as well as tryptophan fluorescence.2 2-Aminopurine inhibits the double-stranded RNA-dependent protein kinase, protein kinase R, whose activity mediates antiviral defense and participates in toll-like receptor signaling.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jean, J.M., and Hall, K.B. 2-Aminopurine fluorescence quenching and lifetimes: Role of base stacking. Proc. Natl. Acad. Sci. USA 98(1), 37-41 (2001).

    2. Holz, B., Klimasauskas, S., Serva, S., et al. 2-Aminopurine as a fluorescent probe for DNA base flipping by methyltransferases. Nucleic Acids Res. 26(4), 1076-1083 (1998).

    3. Endoh, Y., Chung, Y.M., Clark, I.A., et al. IL-10-dependent S100A8 gene induction in monocytes/macrophages by double-stranded RNA. J. Immunol. 182(4), 2258-2268 (2009).