Sequence selective recognition of DNA by hairpin conjugates of a racemic seco-cyclopropaneindoline-2-benzofurancarboxamide and polyamides |
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| Authors: | Toth James L Price Carly A Madsen Erik C Handl Heather L Hudson Stephen J Hubbard Richard B Bowen J Phillip Kiakos Konstantinos Hartley John A Lee Moses |
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| Affiliation: | Department of Chemistry, Furman University, Greenville, SC 29613, USA. |
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| Abstract: | Conjugates of racemic seco-cyclopropaneindoline-2-benzofurancarboxamide (CI-Bf) and four diamides (ImIm 1, ImPy 2, PyIm 3, and PyPy 4, where Py is pyrrole, and Im is imidazole), linked by a gamma-aminobutyrate group were synthesized. In addition to alkylating at adenine-N3 positions within an A(5) sequence, the imidazole-containing compounds 1 and 2 were found to also alkylate purine-N3 positions within a sequence 3'-GGGGGGA(888)CTGCTC(894)-5'. A model for the binding of hairpin conjugates 1 and 2 with the 3'-GACT-5' sequence is proposed. |
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