Issue 24, 2018

Sequence selective photoinduced electron transfer of a pyrene–porphyrin dyad to DNA

Abstract

The binding modes of a pyrene–porphyrin dyad, (1-pyrenyl)-tris(N-methyl-p-pyridino)porphyrin (PyTMpyP), to various DNAs (calf thymus DNA (Ct-DNA), poly[d(G–C)2], and poly[d(A–T)2]) have been investigated using circular dichroism and linear dichroism measurements. Based on the polarization spectroscopic results, it can be shown that the pyrenyl and porphryin planes are skewed to a large extent for PyTMPyP in an aqueous environment and in the binding site of poly[d(G–C)2]. In this complex, a photoinduced electron transfer (PET) process between the pyrenyl and porphyrin moieties occurs. On the other hand, PET was not observed in the PyTMPyP–poly[d(A–T)2] complex, whereas the fluorescence intensity of TMPyP was enhanced. The molecular planes of the pyrene and porphyrin moieties are almost parallel in the poly[d(A–T)2] and Ct-DNA adducts. Moreover, the generation of 1O2 species occurs only for the PyTMPyP–Ct-DNA and PyTMPyP–poly[d(A–T)2] complexes. We discuss the photophysical properties of PyTMPyP which are attributed to the binding patterns and the sequence of DNA bases.

Graphical abstract: Sequence selective photoinduced electron transfer of a pyrene–porphyrin dyad to DNA

Supplementary files

Article information

Article type
Paper
Submitted
22 Mar 2018
Accepted
24 May 2018
First published
24 May 2018

Phys. Chem. Chem. Phys., 2018,20, 16386-16392

Sequence selective photoinduced electron transfer of a pyrene–porphyrin dyad to DNA

M. E. Heo, Y. Lee, K. Hirakawa, S. Okazaki, S. K. Kim and D. W. Cho, Phys. Chem. Chem. Phys., 2018, 20, 16386 DOI: 10.1039/C8CP01870G

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