Cyclic pyrrole-imidazole polyamides targeted to the androgen response element

被引：0

作者：

Chenoweth, David M. ^{[1
]}

Harki, Daniel A. ^{[1
]}

Phillips, John W. ^{[1
]}

Dose, Christian ^{[1
]}

Dervan, Peter B. ^{[1
]}

机构：

[1] Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, United States

来源：

Journal of the American Chemical Society | 2009年 / 131卷 / 20期

关键词：

Hairpin pyrrole-imidazole (Py-Im) polyamides are a class of cell-permeable DNA-binding small molecules that can disrupt transcription factor-DNA binding and regulate endogenous gene expression. The covalent linkage of antiparallel Py-Im ring pairs with an γ-amino acid turn unit affords the classical hairpin Py-Im polyamide structure. Closing the hairpin with a second turn unit yields a cyclic polyamide; a lesser-studied architecture mainly attributable to synthetic Inaccessibility. We have applied our methodology for solution-phase polyamide synthesis to cyclic polyamides with an Improved high-yield cyclization step. Cyclic 8-ring Py-Im polyamides 1-3 target the DNA sequence 5-WGWWCW-3; which corresponds to the androgen response element (ARE) bound by the androgen receptor transcription factor to modulate gene expression. We find that cyclic Py-Im polyamides 1-3 bind DNA with exceptionally high affinities and regulate the expression of AR target genes In cell culture studies; from which we Infer that the cycle Is cell permeable. © 2009 American Chemical Society;

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摘要：

Journal article (JA)

引用

页码：7182 / 7188

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