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Issue 3, 2013
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Light up G-quadruplex DNA with a [2.2.2]heptamethinecyanine dye

Heiko Ihmels*a  and  Laura Thomasa  
Author affiliations

* Corresponding authors

a University of Siegen, Organic Chemistry II, Adolf-Reichwein-Str. 2, Siegen, Germany
E-mail: ihmels@chemie.uni-siegen.de
Tel: +49 (0) 271 740 3440

Abstract

The interactions of a triangle-shaped [2.2.2]heptamethinecyanine dye 1, namely 1,5,7-tris-[3-methylbenzothiazol-2-yl]-[2.2.2]heptamethindiium, with quadruplex DNA were studied with photometric and fluorimetric titrations, thermal DNA denaturation, CD and 1H-NMR spectroscopy. The ligand binds to the quadruplex DNA with moderate affinity (K = 8 × 105 M−1), mainly by terminal π stacking. Remarkably, the ligand 1 exhibits a selectivity for quadruplex DNA relative to duplex DNA. Whereas the cyanine dye is very weakly fluorescent in aqueous solution, the emission intensity increases by a factor of >100 upon association with quadruplex DNA. Thus, it is shown that trinuclear cyanine derivatives may be employed as selective probes for the fluorimetric detection of quadruplex DNA.

Graphical abstract: Light up G-quadruplex DNA with a [2.2.2]heptamethinecyanine dye

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Publication details

The article was received on 10 Sep 2012, accepted on 12 Nov 2012 and first published on 12 Nov 2012


Article type: Paper
DOI: 10.1039/C2OB26779A
Org. Biomol. Chem., 2013,11, 480-487

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    Light up G-quadruplex DNA with a [2.2.2]heptamethinecyanine dye

    H. Ihmels and L. Thomas, Org. Biomol. Chem., 2013, 11, 480
    DOI: 10.1039/C2OB26779A

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