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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 icon 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

Puni tekst: engleski, pdf (2 MB) str. 603-611 preuzimanja: 148* citiraj
APA 6th Edition
Orehovec, I., Glavač, D., Dokli, I., Gredičak, M. i Piantanida, I. (2017). Impact of the Supramolecular Organisation of Pyrene – Quinoline Conjugates on their Interaction with ds – DNA. Croatica Chemica Acta, 90 (4), 603-611. https://doi.org/10.5562/cca3269
MLA 8th Edition
Orehovec, Iva, et al. "Impact of the Supramolecular Organisation of Pyrene – Quinoline Conjugates on their Interaction with ds – DNA." Croatica Chemica Acta, vol. 90, br. 4, 2017, str. 603-611. https://doi.org/10.5562/cca3269. Citirano 18.07.2019.
Chicago 17th Edition
Orehovec, Iva, Danijel Glavač, Irena Dokli, Matija Gredičak i Ivo Piantanida. "Impact of the Supramolecular Organisation of Pyrene – Quinoline Conjugates on their Interaction with ds – DNA." Croatica Chemica Acta 90, br. 4 (2017): 603-611. https://doi.org/10.5562/cca3269
Harvard
Orehovec, I., et al. (2017). 'Impact of the Supramolecular Organisation of Pyrene – Quinoline Conjugates on their Interaction with ds – DNA', Croatica Chemica Acta, 90(4), str. 603-611. doi: https://doi.org/10.5562/cca3269
Vancouver
Orehovec I, Glavač D, Dokli I, Gredičak M, Piantanida I. Impact of the Supramolecular Organisation of Pyrene – Quinoline Conjugates on their Interaction with ds – DNA. Croatica Chemica Acta [Internet]. 2017 [pristupljeno 18.07.2019.];90(4):603-611. doi: https://doi.org/10.5562/cca3269
IEEE
I. Orehovec, D. Glavač, I. Dokli, M. Gredičak i I. Piantanida, "Impact of the Supramolecular Organisation of Pyrene – Quinoline Conjugates on their Interaction with ds – DNA", Croatica Chemica Acta, vol.90, br. 4, str. 603-611, 2017. [Online]. doi: https://doi.org/10.5562/cca3269

Sažetak
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.

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

Ključne riječi
pyrene; quinoline; fluorescence; DNA recognition; excimer emission

Hrčak ID: 198489

URI
https://hrcak.srce.hr/198489

Posjeta: 202 *