Chiral Selectivity in the Binding of [4]Helicene Derivatives to Double-Stranded DNA
Journal article, 2013

The interaction of a series of chiral cationic [4]helicene derivatives, which differ by their substituents, with double-stranded DNA has been investigated by using a combination of spectroscopic techniques, including time-resolved fluorescence, fluorescence anisotropy, and linear dichroism. Addition of DNA to helicene solutions results to a hypochromic shift of the visible absorption bands, an increase of fluorescence quantum yield and lifetime, a slowing down of fluorescence anisotropy decay, and a linear dichroism in flow-oriented DNA, which unambiguously points to the binding of these dyes to DNA. Both helicene monomers and dimeric aggregates, which form at higher concentration, bind to DNA, the former most probably upon intercalation and the latter upon groove binding. The binding constant depends substantially on the dye substituents and is, in all cases, larger with the M than the P enantiomer, by factors ranging from 1.2 to 2.3, depending on the dye.

circular dichroism

helical structures

time-resolved spectroscopy

DNA recognition

fluorescent probes

chirality

Author

Oksana Kel

University of Geneva

Alexandre Fürstenberg

University of Geneva

Nathalie Mehanna

University of Geneva

Cyril Nicolas

University of Geneva

Benoît Laleu

University of Geneva

Martin Hammarson

Chalmers, Chemical and Biological Engineering, Physical Chemistry

Bo Albinsson

Chalmers, Chemical and Biological Engineering, Physical Chemistry

Jerôme Lacour

University of Geneva

Eric Vauthey

University of Geneva

Chemistry - A European Journal

0947-6539 (ISSN) 1521-3765 (eISSN)

Vol. 19 22 7173-7180

Areas of Advance

Nanoscience and Nanotechnology (2010-2017)

Subject Categories

Physical Chemistry

DOI

10.1002/chem.201203915

More information

Latest update

6/15/2018