Issue 3, 2010
From the journal:

New Journal of Chemistry

Cationic side-chains control DNA/RNA binding properties and antiproliferative activity of dicationic dibenzotetraaza[14]annulene derivatives†

Marijana Radić Stojković,a   Marko Marjanović,c   Dariusz Pawlica,b   Lukasz Dudek,b   Julita Eilmes,b   Marijeta Kraljc  and  Ivo Piantanida*a  

* Corresponding authors

a Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, PO Box 180, HR-10002 Zagreb, Croatia
E-mail: pianta@irb.hr

b Department of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Kraków, Poland
E-mail: jeilmes@chemia.uj.edu.pl

c Division of Molecular Medicine, Ruđer Bošković Institute, Bijenička cesta 54, P. O. Box 180, HR-10002 Zagreb, Croatia
E-mail: mhorvat@irb.hr

Abstract

Studied dicationic dibenzotetraaza[14]annulene derivatives intercalate into synthetic double stranded DNA and RNA, while their positively charged side-chains additionally interact within the minor groove of polynucleotides, contributing to the overall affinity of compounds and controlling pronounced A–T(U) over G–C sequence preference as well as stronger thermal stabilization of ds-DNA than ds-RNA. Furthermore, all compounds showed moderate to high antiproliferative activity against five human tumour cell lines, whereby clear correlation between the structure of the side-chain and cytotoxic activity was observed.

Graphical abstract: Cationic side-chains control DNA/RNA binding properties and antiproliferative activity of dicationic dibenzotetraaza[14]annulene derivatives

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Article information

DOI
https://doi.org/10.1039/B9NJ00490D
Article type
Paper
Submitted
17 Sep 2009
Accepted
23 Nov 2009
First published
15 Jan 2010

New J. Chem., 2010,34, 500-507

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Cationic side-chains control DNA/RNA binding properties and antiproliferative activity of dicationic dibenzotetraaza[14]annulene derivatives

M. R. Stojković, M. Marjanović, D. Pawlica, L. Dudek, J. Eilmes, M. Kralj and I. Piantanida, New J. Chem., 2010, 34, 500 DOI: 10.1039/B9NJ00490D

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