2004
DOI: 10.1093/nar/gkh609
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Influence of structural variation on nuclear localization of DNA-binding polyamide-fluorophore conjugates

Abstract: A pivotal step forward in chemical approaches to controlling gene expression is the development of sequence-specific DNA-binding molecules that can enter live cells and traffic to nuclei unaided. DNA-binding polyamides are a class of programmable, sequence-specific small molecules that have been shown to influence a wide variety of protein-DNA interactions. We have synthesized over 100 polyamide-fluorophore conjugates and assayed their nuclear uptake profiles in 13 mammalian cell lines. The compiled dataset, c… Show more

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Cited by 92 publications
(97 citation statements)
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“…Furthermore, the chiral turn allows stereochemical control, enforcing the N→C polyamide alignment with respect to the 5'→3' orientation of the adjacent DNA strand. 29,30 The microstructure of DNA is sequence-dependent, and polyamides composed of Py and Im rings are overly curved compared to the DNA minor groove. Aliphatic β-alanine residues have been incorporated at internal positions to reset the register between contiguous aromatic ring pairings.…”
Section: Hairpin Polyamide Motifmentioning
confidence: 99%
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“…Furthermore, the chiral turn allows stereochemical control, enforcing the N→C polyamide alignment with respect to the 5'→3' orientation of the adjacent DNA strand. 29,30 The microstructure of DNA is sequence-dependent, and polyamides composed of Py and Im rings are overly curved compared to the DNA minor groove. Aliphatic β-alanine residues have been incorporated at internal positions to reset the register between contiguous aromatic ring pairings.…”
Section: Hairpin Polyamide Motifmentioning
confidence: 99%
“…28 The acetylated turn linkage used in the design of compounds 1, 3, and 5 has been shown to improve nuclear localization in some human cancer cell lines. 29,30 Polyamides 1-5 were synthesized on oxime resin according to published manual solidphase synthesis protocols. 31,32 Fluorescein and isophthalic acid conjugations, as well as the subsequent deprotection and acetylation steps, were performed according to published methods.…”
Section: ' -G C a C C T T T G T T A T G C A T C T G C C G -3 ' 3 ' -Cmentioning
confidence: 99%
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