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Bifunctional Rhodium Intercalator Conjugates as Mismatch-Directing DNA Alkylating Agents

Schatzschneider, Ulrich and Barton, Jacqueline K. (2004) Bifunctional Rhodium Intercalator Conjugates as Mismatch-Directing DNA Alkylating Agents. Journal of the American Chemical Society, 126 (28). pp. 8630-8631. ISSN 0002-7863. doi:10.1021/ja048543m.

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A conjugate of a DNA mismatch-specific rhodium intercalator, containing the bulky chrysenediimine ligand, and an aniline mustard has been prepared, and targeting of mismatches in DNA by this conjugate has been examined. The preferential alkylation of mismatched over fully matched DNA is found by a mobility shift assay at concentrations where untethered organic mustards show little reaction. The binding site of the Rh intercalator was determined by DNA photocleavage, and the position of covalent modification was established on the basis of the enhanced depurination associated with N-alkylation. The site-selective alkylation at mismatched DNA renders these conjugates useful tools for the covalent tagging of DNA base pair mismatches and new chemotherapeutic design.

Item Type:Article
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Barton, Jacqueline K.0000-0001-9883-1600
Additional Information:© 2004 American Chemical Society. Received March 12, 2004. Publication Date (Web): June 24, 2004. We are grateful to the NIH (GM33309) for their financial support. We also thank the Deutsche Forschungsgemeinschaft for a postdoctoral fellowship (U.S.).
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Deutsche Forschungsgemeinschaft (DFG)UNSPECIFIED
Issue or Number:28
Record Number:CaltechAUTHORS:20160209-121614706
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Official Citation:Bifunctional Rhodium Intercalator Conjugates as Mismatch-Directing DNA Alkylating Agents Ulrich Schatzschneider and Jacqueline K. Barton Journal of the American Chemical Society 2004 126 (28), 8630-8631 DOI: 10.1021/ja048543m
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:64334
Deposited By: George Porter
Deposited On:09 Feb 2016 21:09
Last Modified:10 Nov 2021 23:29

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