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A Mismatch-Selective Bifunctional Rhodium−Oregon Green Conjugate: A Fluorescent Probe for Mismatched DNA

Zeglis, Brian M. and Barton, Jacqueline K. (2006) A Mismatch-Selective Bifunctional Rhodium−Oregon Green Conjugate: A Fluorescent Probe for Mismatched DNA. Journal of the American Chemical Society, 128 (17). pp. 5654-5655. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20160209-124007376

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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 ^(32)P-labeled oligonucleotides indicate that the conjugate selectively binds the mismatched DNA with a binding affinity of 6 × 10^5 M^(-1) and, upon irradiation, cleaves the DNA backbone neighboring the mismatched site.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja061409cDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja061409cPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja061409cPublisherSupporting Information
ORCID:
AuthorORCID
Barton, Jacqueline K.0000-0001-9883-1600
Additional Information:© 2006 American Chemical Society. Received February 28, 2006. Publication Date (Web): April 7, 2006. We are grateful to the NIH (GM33309) for their financial support and the NSF for a graduate fellowship to B.M.Z. We also thank G. Mathis for technical assistance.
Funders:
Funding AgencyGrant Number
NIHGM33309
NSF Graduate Research FellowshipUNSPECIFIED
Issue or Number:17
Record Number:CaltechAUTHORS:20160209-124007376
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160209-124007376
Official Citation:A Mismatch-Selective Bifunctional Rhodium−Oregon Green Conjugate:  A Fluorescent Probe for Mismatched DNA Brian M. Zeglis and Jacqueline K. Barton Journal of the American Chemical Society 2006 128 (17), 5654-5655 DOI: 10.1021/ja061409c
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:64339
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:09 Feb 2016 21:29
Last Modified:03 Oct 2019 09:36

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