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Issue 6, 2010
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On the selective detection of duplex deoxyribonucleic acids by 2,1,3-benzothiadiazole fluorophores

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Abstract

A series of 4,7-π-extended 2,1,3-benzothiadiazoles (BTDs) with different molecular architectures, in particular, the organic dyes based on the 4-(arylethynyl)-7-(4-methoxy)-2,1,3-benzothiazole skeleton, can be used at very low concentrations (down to 10 μM) to detect DNA at 1 ppm in phosphate buffer solutions. Upon binding to DNA, these dyes showed an exponential increase in the fluorescence intensity (hyperchromic effect) and a red shift (1–5 nm) in the long-wavelength emission maxima. Pre-steady state kinetic experiments (stopped-flow) demonstrated the fast dye interaction with the biomacromolecules of DNA with an increase in fluorescence, especially with non-symmetrical BTDs containing an ethynyl spacer. An intercalation model could be proposed based on the photophysical properties, X-ray analysis, and theoretical calculations (ab initio). In this model, the intercalation occurs on the ethynyl side of the BTD, and as a consequence, the PhOMe portion is free to perform the ICT process with the BTD core and stabilizes it in the excited state.

Graphical abstract: On the selective detection of duplex deoxyribonucleic acids by 2,1,3-benzothiadiazole fluorophores

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Publication details

The article was received on 16 Sep 2009, accepted on 13 Jan 2010 and first published on 05 Mar 2010


Article type: Paper
DOI: 10.1039/B919155K
Citation: Mol. BioSyst., 2010,6, 967-975
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    On the selective detection of duplex deoxyribonucleic acids by 2,1,3-benzothiadiazole fluorophores

    B. A. D. Neto, A. A. M. Lapis, F. S. Mancilha, E. L. Batista Jr., P. A. Netz, F. Rominger, L. A. Basso, D. S. Santos and J. Dupont, Mol. BioSyst., 2010, 6, 967
    DOI: 10.1039/B919155K

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