A mismatch-selective bifunctional rhodium-Oregon Green conjugate: a fluorescent probe for mismatched DNA

Journal of the American Chemical Society
Brian M Zeglis, Jacqueline K Barton

Abstract

A fluorescent metallointercalator conjugate that selectively targets DNA base mismatches has been synthesized by coupling an organic fluorophore to a bulky Rh intercalator containing the chrysenequinone diimine ligand. Ion pairing between the cationic Rh and anionic fluorophore moieties dramatically quenches the fluorescence of the conjugate in solution and in the presence of matched DNA. However, in the presence of mismatched DNA, the fluorescence of the conjugate is increased >300%. This increase in fluorescence is attributed to the loss in intramolecular quenching associated with DNA binding; intercalation of the Rh moiety into the mismatched site can lead to electrostatic repulsion of the anionic fluorophore away from the DNA phosphate backbone and Rh. Denaturing PAGE experiments with 32P-labeled oligonucleotides indicate that the conjugate selectively binds the mismatched DNA with a binding affinity of 6 x 105 M-1 and, upon irradiation, cleaves the DNA backbone neighboring the mismatched site.

References

May 18, 2001·Nature·J H Hoeijmakers
Mar 1, 2003·Proceedings of the National Academy of Sciences of the United States of America·Henrik JunickeJacqueline K Barton
Jul 15, 2004·Journal of the American Chemical Society·Ulrich Schatzschneider, Jacqueline K Barton
Jul 20, 2004·Inorganic Chemistry·Eva RübaJacqueline K Barton

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Citations

Oct 25, 2007·Journal of Fluorescence·Fang-Ying WuJong-In Hong
Oct 9, 2007·Inorganic Chemistry·Mi Hee LimJacqueline K Barton
Jun 26, 2008·Inorganic Chemistry·Brian M Zeglis, Jacqueline K Barton
May 21, 2009·Inorganic Chemistry·Mi Hee LimJacqueline K Barton
Sep 20, 2007·Journal of the American Chemical Society·Christine CordierJacqueline K Barton
May 22, 2008·Journal of the American Chemical Society·Brian M ZeglisJacqueline K Barton
Apr 5, 2007·Nature Protocols·Brian M Zeglis, Jacqueline K Barton
Dec 6, 2006·Chemical Communications : Chem Comm·Nina MoranJames H R Tucker
Nov 9, 2007·Chemical Communications : Chem Comm·Brian M ZeglisJacqueline K Barton
Nov 13, 2015·Analytical Chemistry·Jiahao HuangZhigang Li
Mar 19, 2014·Chemical Society Reviews·Anton GranzhanMarie-Paule Teulade-Fichou
Nov 7, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Alessio TerenziGiampaolo Barone
Dec 31, 2008·Chemistry : a European Journal·Anton Granzhan, Marie-Paule Teulade-Fichou
Sep 2, 2009·The Journal of Physical Chemistry. B·Yan-Zi MaKe-Zhi Wang
Apr 6, 2018·Journal of the American Chemical Society·Kelsey M Boyle, Jacqueline K Barton
Sep 22, 2012·Journal of the American Chemical Society·Evan A WeitzValerie C Pierre

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