Sequence selective recognition of DNA by hairpin conjugates of a racemic seco-cyclopropaneindoline-2-benzofurancarboxamide and polyamides

Authors

James L. Toth
Carly A. Price
Erik C. Madsen
Heather L. Handl
Stephen J. Hudson
III R. Hubbard
J. P. Bowen
Konstantinos Kiakos
John A. Hartley
Moses Lee

ACS Citation

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.

Version of Record

10.1016/S0960-894X(02)00341-4

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 γ-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 3-²-GGGGGGA(888)CTGCTC(894)-5-². A model for the binding of hairpin conjugates 1 and 2 with the 3-²-GACT-5-² sequence is proposed.

Source Name

Bioorganic & Medicinal Chemistry Letters

Publication Date

1-1-2002

Volume

12

Issue

16

Page(s)

933-940

Document Type

Citation

Citation Type

Article