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Sequence-Specific DNA Recognition by Cyclic Pyrrole-Imidazole Cysteine-Derived Polyamide Dimers

Authors :
Kaori Hashiya
Hiroshi Sugiyama
Yusuke Kawamoto
Hironobu Morinaga
Toshikazu Bando
Makoto Yamamoto
Source :
Chemistry - A European Journal. 20:752-759
Publication Year :
2013
Publisher :
Wiley, 2013.

Abstract

Pyrrole-imidazole (PI) polyamides bind to the minor groove of the DNA duplex in a sequence-specific manner and thus have the potential to regulate gene expression. To date, various types of PI polyamides have been designed as sequence-specific DNA binding ligands. One of these, cysteine cyclic PI polyamides containing two β-alanine molecules, were designed to recognize a 7 bp DNA sequence with high binding affinity. In this study, an efficient cyclization reaction between a cysteine and a chloroacetyl residue was used for dimerization in the synthesis of a unit that recognizes symmetrical DNA sequences. To evaluate specific DNA binding properties, dimeric PI polyamide binding was measured by using a surface plasmon resonance (SPR) method. Extending this molecular design, we synthesized a large dimeric PI polyamide that can recognize a 14 bp region in duplex DNA.

Details

ISSN :
09476539
Volume :
20
Database :
OpenAIRE
Journal :
Chemistry - A European Journal
Accession number :
edsair.doi.dedup.....fa300d9d4a26dbd0ca6405976fb77893
Full Text :
https://doi.org/10.1002/chem.201302482