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Issue 9, 2012
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Labelling of nucleosides and oligonucleotides by solvatochromic 4-aminophthalimide fluorophore for studying DNA–protein interactions

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Abstract

Solvatochromic fluorescent 4-aminophthalimide (API) and 4-(N,N-dimethylamino)phthalimide (DAPI) were attached covalently to 2′-deoxycytidine or -adenosine via a non-conjugated propargyl linker by Sonogashira cross-coupling reactions of N-propargylphthalimides with halogenated nucleosides. The nucleosides were phosphorylated to triphosphates and enzymatically incorporated into oligonucleotides by DNA polymerases. API-labelled DNA was used for the detection of DNA protein interactions with either the sequence-specific p53 protein or a non-specific single strand binding (SSB) protein. Both proteins changed the polarity around the fluorophore and increased (2–3 fold) the intensity of API fluorescence.

Graphical abstract: Labelling of nucleosides and oligonucleotides by solvatochromic 4-aminophthalimide fluorophore for studying DNA–protein interactions

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Publication details

The article was received on 02 Apr 2012, accepted on 15 Jun 2012 and first published on 15 Jun 2012


Article type: Edge Article
DOI: 10.1039/C2SC20404E
Citation: Chem. Sci., 2012,3, 2797-2806
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    Labelling of nucleosides and oligonucleotides by solvatochromic 4-aminophthalimide fluorophore for studying DNA–protein interactions

    J. Riedl, R. Pohl, N. P. Ernsting, P. Orság, M. Fojta and M. Hocek, Chem. Sci., 2012, 3, 2797
    DOI: 10.1039/C2SC20404E

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