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Issue 7, 2010
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DNA base-pair flipping with fluorescent perylenediimide pincers

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Abstract

The synthesis, structure, and electronic spectra of a series of DNA hairpins possessing two perylenediimide (PDI) base pair surrogates are reported. The PDI chromophores are located in opposite strands of the hairpin base pair domain opposite abasic sites and are either adjacent to each other or separated by a variable number of AT or GC base pairs. Molecular modeling of the conjugate having adjacent PDI chromophores shows that they adopt a slipped, π-stacked geometry with an angle of 40° between the PDI long axes. The electronic absorption, fluorescence, and circular dichroism of this conjugate are consistent with a stacked PDI structure. Conjugates having one or two GC base pairs between the PDI chromophores display spectra that are consistent with isolated PDIs. Conjugates having 1–4 AT base pairs have more complex spectra, suggestive of an equilibrium between base paired and flipped structures having stacked PDIs. Heating of the conjugates possessing isolated PDI chromophores results in base pair flipping. The free energy for PDI stacking is greater than that for a single AT base pair and comparable to that for a single GC base pair or two AT base pairs.

Graphical abstract: DNA base-pair flipping with fluorescent perylenediimide pincers

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Publication details

The article was received on 03 Mar 2010, accepted on 07 Apr 2010 and first published on 29 Apr 2010


Article type: Paper
DOI: 10.1039/C0PP00044B
Photochem. Photobiol. Sci., 2010,9, 916-922

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    DNA base-pair flipping with fluorescent perylenediimide pincers

    T. A. Zeidan, M. Hariharan, K. Siegmund and F. D. Lewis, Photochem. Photobiol. Sci., 2010, 9, 916
    DOI: 10.1039/C0PP00044B

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