Original scientific paper

https://doi.org/10.5562/cca3269

Impact of the Supramolecular Organisation of Pyrene – Quinoline Conjugates on their Interaction with ds – DNA

Iva Orehovec ; Laboratory for Biomolecular Interactions and Spectroscopy, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000, Zagreb, Croatia
Danijel Glavač ; Laboratory for Biomimetic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000, Zagreb, Croatia
Irena Dokli ; Laboratory for stereoselective catalysis and biocatalysis, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000, Zagreb, Croatia
Matija Gredičak ; Laboratory for Biomimetic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000, Zagreb, Croatia
Ivo Piantanida orcid.org/0000-0002-9933-446X ; Laboratory for Biomolecular Interactions and Spectroscopy, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000, Zagreb, Croatia

Abstract

Two novel pyrene – quinoline conjugates differing in the linker flexibility between aryls were prepared. In comparison with referent pyrene derivative, both conjugates showed intramolecular pyrene – quinoline stacking in aqueous medium, much more efficient for rigid conjugate. Consequently, only rigid conjugate showed excimer fluorescence with exceptionally strong bathochromic shift (+ 55 nm) of emission maximum in respect to referent pyrene analogue and flexible conjugate. All studied compounds showed similar, 10 µmol dm−3 affinity toward ds – DNA, characterised in general by fluorescence quenching. The flexible conjugate showed at large excess of DNA over dye formation of pyrene – quinoline excimer, while rigid conjugate retained excimer emission throughout all DNA concentrations. Lack of significant thermal stabilisation of ds – DNA by studied compounds and minor changes in CD spectrum of DNA supported non – specific agglomeration of both conjugates and referent pyrene analogue within hydrophobic DNA grooves as the dominant binding mode.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

pyrene; quinoline; fluorescence; DNA recognition; excimer emission

Hrčak ID:

198489

URI

https://hrcak.srce.hr/198489

Publication date:

29.12.2017.

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