Issue 7, 2019

Elucidating DNA binding of dithienylethenes from molecular dynamics and dichroism spectra

Abstract

DNA binding modes of the stereoisomeric rotamers of two dithenylethene derivatives (DTE1 and DTE2) representing candidate molecular photoswitches of great promise for photopharmacology and nanotechnology have been identified and characterized in terms of their binding energies and electronic circular dichroism (CD) responses. In the open form, two binding modes are identified namely minor-groove binding of the lowest-energy conformer with an anti-parallel arrangement of methyl groups and major-groove double-intercalation of the P-enantiomers of an intermediate-state rotamer. Only the latter binding mode is found to be enantiomerically selective and expected to have an overall negative linear dichroism (LD) as observed in the experiment for DTE1 (Angew. Chem., Int. Ed., 2013, 52, 4393). In the closed form, the most favorable binding mode is found to be minor groove binding. Also this binding mode is found to be enantiomerically selective and for DTE1, it is the M-enantiomer that binds the strongest, showing a positive theoretical signature CD band in the long wavelength region with origin in pyridinium ligands. The theoretical CD spectrum is found to be in good agreement with the experimental one, which provides an indirect evidence for a correct identification of the binding mode in the closed form.

Graphical abstract: Elucidating DNA binding of dithienylethenes from molecular dynamics and dichroism spectra

Supplementary files

Article information

Article type
Paper
Submitted
21 Aug 2018
Accepted
16 Oct 2018
First published
16 Oct 2018
This article is Open Access
Creative Commons BY-NC license

Phys. Chem. Chem. Phys., 2019,21, 3637-3643

Elucidating DNA binding of dithienylethenes from molecular dynamics and dichroism spectra

M. Linares, H. Sun, M. Biler, J. Andréasson and P. Norman, Phys. Chem. Chem. Phys., 2019, 21, 3637 DOI: 10.1039/C8CP05326J

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