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Expanding the repertoire of heterocycle ring pairs for programmable minor groove DNA recognition

Marques, Michael A. and Doss, Raymond M. and Foister, Shane and Dervan, Peter B. (2004) Expanding the repertoire of heterocycle ring pairs for programmable minor groove DNA recognition. Journal of the American Chemical Society, 126 (33). pp. 10339-10349. ISSN 0002-7863. doi:10.1021/ja0486465.

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The discrimination of the four Watson−Crick base pairs by minor groove DNA-binding polyamides have been attributed to the specificity of three five-membered aromatic amino acid subunits, 1-methyl-1H-imidazole (Im), 1-methyl-1H-pyrrole (Py), and 3-hydroxy-1H-pyrrole (Hp) paired four different ways. The search for additional ring pairs that demonstrate DNA-sequence specificity has led us to a new class of 6−5 fused bicycle rings as minor groove recognition elements. The affinities and specificities of the hydroxybenzimidazole/pyrrole (Hz/Py) and hydroxybenzimidazole/benzimidazole (Hz/Bi) pairs for each of the respective Watson−Crick base pairs within the sequence context 5‘-TGGXCA-3‘ (X = A, T, G, C) were measured by quantitative DNaseI footprinting titrations. The Hz/Py and Hz/Bi distinguish T·A from A·T. Hairpin polyamides containing multiple Hz/Py pairs were examined and were shown to mimic the Hp/Py pair with regard to affinity and specificity. Therefore, the Hz/Py pair may be considered a second-generation replacement for the Hp/Py pair.

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Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 2004 American Chemical Society. Received March 9, 2004; Publication Date (Web): July 28, 2004. We thank the National Institutes of Health for grant support, Caltech for a James Irvine Fellowship to R.M.D., the Parsons Foundation Fellowship to M.A.M, and the NSF for a fellowship to S.F. We also thank C. Brindle for preparing some intermediates.
Funding AgencyGrant Number
James Irvine FoundationUNSPECIFIED
Ralph M. Parsons FoundationUNSPECIFIED
Issue or Number:33
Record Number:CaltechAUTHORS:20160509-114911306
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Official Citation:Expanding the Repertoire of Heterocycle Ring Pairs for Programmable Minor Groove DNA Recognition Michael A. Marques, Raymond M. Doss, Shane Foister, and Peter B. Dervan Journal of the American Chemical Society 2004 126 (33), 10339-10349 DOI: 10.1021/ja0486465
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66769
Deposited By: Victoria Brennan
Deposited On:17 May 2016 23:08
Last Modified:11 Nov 2021 00:02

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