A photoreactive nucleic acid crosslinking probe
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4'-Aminomethyl-4,5',8-trimethylpsoralen

Item No. 17162

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(aminomethyl)-2,5,9-trimethyl-7H-furo[3,2-g][1]benzopyran-7-one
CAS Number
64358-50-5
Synonyms
  • 4'-Aminomethyltrioxsalen
Molecular Formula
C15H15NO3
Formula Weight
257.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/mlEthanol: 1 mg/ml
λmax
240, 287 nm
SMILES
O=C1OC2=C(C)C3=C(C(CN)=C(C)O3)C=C2C(C)=C1
InChi Code
InChI=1S/C15H15NO3/c1-7-4-13(17)19-14-8(2)15-11(5-10(7)14)12(6-16)9(3)18-15/h4-5H,6,16H2,1-3H3
InChi Key
WBIICVGYYRRURR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $128

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    10 mg

    $236

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    Product Description

    4'-Aminomethyl-4,5',8-trimethylpsoralen is a bifunctional photoreactive agent for crosslinking nucleic acids.1,2 In the dark, it intercalates into double-stranded regions in DNA or RNA. Upon long wavelength UV irradiation (e.g., 365 nm), 4'-aminomethyl-4,5',8-trimethylpsoralen first forms a covalent monoadduct with a pyrimidine base, followed by covalently linking with an adjacent pyrimidine on the opposite strand.1,2 Short wavelength UV irradiation (e.g., 254 nm) reverses this reaction. 4'-Aminomethyl-4,5',8-trimethylpsoralen has a high binding affinity for RNA and has been used to study different types of RNA from diverse organisms, including viruses.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Liarakos, C.D., Reinhart, G., Kopper, R.A., et al. Characterization of the effects on ovalbumin mRNA of aminomethyl-trimethylpsoralen photoreaction with hen oviduct mRNA. Nucleic Acids Res. 15(20), 8417-8438 (1987).

    2. Garrett-Wheeler, E., Lockard, R.E., and Kumar, A. Mapping of psoralen cross-linked nucleotides in RNA. Nucleic Acids Res. 12(7), 3405-3423 (1984).

    3. Hearst, J.E., and Thiry, L. The photoinactivation of an RNA animal virus, vesicular stomatitis virus, with the aid of newly synthesized psoralen derivatives. Nucleic Acids Res. 4(5), 1339-1347 (1977).

    4. Hui, C.F., and Cantor, C.R. Mapping the location of psoralen crosslinks on RNA by mung bean nuclease sensitivity of RNA-DNA hybrids. Proc. Natl. Acad. Sci. USA 82(5), 1381-1385 (1985).

    5. Raviprakash, K., Sun, P., Raviv, Y., et al. Dengue virus photo-inactivated in presence of 1,5-iodonaphthylazide (INA) or AMT, a psoralen compound (4'-aminomethyl-trioxsalen) is highly immunogenic in mice. Hum. Vaccin. Immunother. 9(11), 2336-2341 (2013).