Original scientific paper

https://doi.org/10.5562/cca2141

Synthesis, DNA Interactions and Anticancer Evaluation of Novel Diamidine Derivatives of 3,4-Ethylenedioxythiophene

Ivana Stolić ; Department of Chemistry and Biochemistry, Faculty of Veterinary Medicine, University of Zagreb, Heinzelova 55, HR-10000 Zagreb, Croatia
Monika Avdičević ; University Hospital Centre Osijek, Huttlerova 4, HR-31000 Osijek, Croatia
Nikola Bregović ; Division of Physical Chemistry, Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Ivo Piantanida ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P.O. Box 180, HR-10000 Zagreb, Croatia
Ljubica Glavaš-Obrovac ; University Hospital Centre Osijek, Huttlerova 4, HR-31000 Osijek, Croatia;Faculty of Medicine, J. J. Strossmayer University of Osijek, Huttlerova 4, HR-31000 Osijek, Croatia
Miroslav Bajić orcid.org/0000-0003-1686-0294 ; Department of Chemistry and Biochemistry, Faculty of Veterinary Medicine, University of Zagreb, Heinzelova 55, HR-10000 Zagreb, Croatia

Abstract

Eight novel diamidino 3,4-ethylenedioxythiophene-2,5-dicarboxanilides (5a–h), obtained by condensation reaction of 3,4-ethylenedioxythiophene-2,5-dicarbonyl chloride and corresponding 3- or 4-aminobenzamidines, were evaluated for interactions with double-stranded DNA and RNA, and their cyto-toxicity was assayed against the panel of human cancer cell lines. All compounds preferentially bind into the minor groove of DNA and had higher affinity for DNA than for RNA. Compounds 5a–h showed a moderate antiproliferative effect toward the panel of seven carcinoma cells line, whereby the highest inhi-bitory potential was displayed by compound 5a with unsubstituted amidino moieties in para position. (doi: 10.5562/cca2141)

Keywords

amide-amidines; 3,4-ethylenedioxythiophene; diarylamidine; DNA/RNA binding; antitumor activity

Hrčak ID:

94443

URI

https://hrcak.srce.hr/94443

Publication date:

17.12.2012.

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