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Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA

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2013
Authors
Vujčić, Miroslava
Tufegdžić, Srđan
Novaković, Irena
Djikanovic, Daniela
Gašić, Miroslav J.
Sladić, Dušan
Article (Published version)
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Abstract
The interactions of avarone, a quinone from the marine sponge Dysideaavara, and the methylamino derivatives of avarone (2), 3'-(methylamino)avarone (3) and 4'-(methylamino)avarone (4) with calf thymus DNA (CT-DNA) were studied. Agarose gel electrophoreticanalysis showed that binding of the quinones quenched fluorescence of ethidium bromide (EB). The extent of fluorescence quenching of intercalator EB by competitive displacement from EB-CT-DNA system and of groove binder Hoechst 33258 (H) from H-CT-DNA system with the quinones was analyzed by fluorescence spectroscopy. The obtained results demonstrated that the quinones reduced binding of both the intercalator EB and the minor groove binder H, indicating possible degradation of DNA. The substituent on the quinone moiety determined the extent of DNA damaging effect of the quinone, which was the most extensive with 3'-(methylamino)avarone and the least extensive with its regioisomer 4'-(methylamino)avarone. The results were confirmed by t...he observed hyperchromic effects in UV-visible spectra measured after interactions of the derivatives with CT-DNA.

Keywords:
Avarol / Avarone / 3 '-(Methylamino)avarone / 4 '-(Methylamino)avarone / Calf thymus DNA / Fluorescence measurements
Source:
International Journal of Biological Macromolecules, 2013, 62, 405-410
Publisher:
  • Elsevier Science Bv, Amsterdam
Projects:
  • Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (RS-172055)

DOI: 10.1016/j.ijbiomac.2013.09.013

ISSN: 0141-8130

PubMed: 24080453

WoS: 000329881200060

Scopus: 2-s2.0-84886041638
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/1237
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IHTM

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