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Targeting Abasic Sites and Single Base Bulges in DNA with Metalloinsertors

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Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125
[email protected]
Cite this: J. Am. Chem. Soc. 2008, 130, 24, 7530–7531
Publication Date (Web):May 21, 2008
https://doi.org/10.1021/ja801479y
Copyright © 2008 American Chemical Society
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    Abstract

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    The site-specific recognition of abasic sites and single base bulges in duplex DNA by sterically expansive rhodium metalloinsertors has been investigated. Through DNA photocleavage experiments, Rh(bpy)2(chrysi)3+ is shown to bind both abasic sites and single base bulges site-specifically and, upon irradiation, to cleave the backbone of the defect-containing DNA. Photocleavage titrations reveal that the metal complex binds DNA containing an abasic site with high affinity (2.6(5) × 106 M−1), comparably to the metalloinsertor and a CC mismatch. The complex binds single base bulge sites with lower affinity (∼105 M−1). Analysis of cleavage products and the correlation of affinities with helix destabilization suggest that Rh(bpy)2(chrysi)3+ binds both lesions via metalloinsertion, as observed for Rh binding at mismatched sites, a binding mode in which the mismatched or unpaired bases are extruded from the helix and replaced in the base stack by the sterically expansive ligand of the metalloinsertor.

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    Photocleavage titrations, gel analysis, and mass spectral data. This material is available free of charge via the Internet at http://pubs.acs.org.

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