Sequence selective recognition of DNA by hairpin conjugates of a racemic seco-cyclopropaneindoline-2-benzofurancarboxamide and polyamides
Toth, J. L.; Price, C. A.; Madsen, E. C.; Handl, H. L.; Hudson, S. J.; Hubbard, I., R.; Bowen, J. P.; Kiakos, K.; Hartley, J. A.; Lee, M. Sequence selective recognition of DNA by hairpin conjugates of a racemic seco-cyclopropaneindoline-2-benzofurancarboxamide and polyamides. Bioorg. Med. Chem. Lett. 2002, 12, 2245-2248.
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 Î³-aminobutyrate group were synthesized. In addition to alkylating at adenine-N3 positions within an A5 sequence, the imidazole-containing compounds 1 and 2 were found to also alkylate purine-N3 positions within a sequence 3â€²-GGGGGGA(888)CTGCTC(894)-5â€². A model for the binding of hairpin conjugates 1 and 2 with the 3â€²-GACT-5â€² sequence is proposed.
Bioorganic & Medicinal Chemistry Letters