Issue 6, 2010
From the journal:

Molecular BioSystems

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

Brenno A. D. Neto,*ac   Alexandre A. M. Lapis,bc   Fabiana S. Mancilha,c   Eraldo L. Batista Jr.,d   Paulo A. Netz,c   Frank Rominger,e   Luiz A. Basso,d   Diógenes S. Santosd  and  Jaïrton Dupont*c  

* Corresponding authors

a Laboratory of Medicinal and Technological Chemistry, University of Brasília (IQ-UnB), Brasilia, DF, Brazil
E-mail: brenno.ipi@gmail.com
Fax: +55 (61) 32734149
Tel: +55 (61) 31073867

b Universidade Federal do Pampa, Unipampa, Bagé, RS, Brazil

c Laboratory of Molecular Catalysis, IQ-UFRGS, RS, Porto Alegre-RS – Brazil, Brazil
E-mail: jairton.dupont@ufrgs.br
Fax: + 55 (51) 33087304
Tel: + 55 (51) 33086321

d Instituto Nacional de Ciência e Tecnologia em Tuberculose (INCT-TB), Centro de Pesquisas em Biologia Molecular e Funcional (CPBMF), Tecnopuc, PUCRS, Brazil

e Organisch-Chemisches Institut der Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B919155K
Article type
Paper
Submitted
16 Sep 2009
Accepted
13 Jan 2010
First published
05 Mar 2010

Mol. BioSyst., 2010,6, 967-975

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements