Sequence selective recognition of DNA by hairpin conjugates of a racemic seco-cyclopropaneindoline-2-benzofurancarboxamide and polyamides.
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.
Toth
James L
JL
Department of Chemistry, Furman University, Greenville, SC 29613, USA.
Price
Carly A
CA
Madsen
Erik C
EC
Handl
Heather L
HL
Hudson
Stephen J
SJ
Hubbard
Richard B
RB
Bowen
J Phillip
JP
Kiakos
Konstantinos
K
Hartley
John A
JA
Lee
Moses
M
D000478:Alkylation; D000577:Amides / Q000737:chemistry / Q000378:metabolism*; D001483:Base Sequence; D001572:Benzofurans / Q000737:chemistry / Q000378:metabolism*; D001665:Binding Sites; D004247:DNA / Q000235:genetics* / Q000378:metabolism*; D007093:Imidazoles / Q000737:chemistry*; D008968:Molecular Conformation; D011758:Pyrroles / Q000737:chemistry*; D013379:Substrate Specificity
D000577:Amides; D001572:Benzofurans; D007093:Imidazoles; D011758:Pyrroles; D004247:DNA