ArticleJournal of the American Chemical Society2008
Next generation hairpin polyamides with (R)-3,4-diaminobutyric acid turn unit.
Article in Journal of the American Chemical Society, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 57 citations in OpenAlex.
- RNA polymerase II trapped on a molecular treadmill: Structural basis of persistent transcriptional arrest by a minor groove DNA binder.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- Natural and Synthetic Oligoarylamides: Privileged Structures for Medical Applications.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Sequence specific suppression of androgen receptor-DNA binding in vivo by a Py-Im polyamide.Nucleic acids research · 2019Article
- RNA polymerase II senses obstruction in the DNA minor groove via a conserved sensor motif.Proceedings of the National Academy of Sciences of the United States of America · 2016Article
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- Animal toxicity of hairpin pyrrole-imidazole polyamides varies with the turn unit.Journal of medicinal chemistry · 2013Article
- Structure-based DNA-targeting strategies with small molecule ligands for drug discovery.Medicinal research reviews · 2013Review
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- Antitumor activity of a pyrrole-imidazole polyamide.Proceedings of the National Academy of Sciences of the United States of America · 2013Article
- Synthesis of cyclic Py-Im polyamide libraries.The Journal of organic chemistry · 2013Article
- Addressable and unidirectional energy transfer along a DNA three-way junction programmed by pyrrole-imidazole polyamides.Scientific reports · 2013Article
- Guiding the design of synthetic DNA-binding molecules with massively parallel sequencing.Journal of the American Chemical Society · 2012Article
- Single-dose pharmacokinetic and toxicity analysis of pyrrole-imidazole polyamides in mice.Cancer chemotherapy and pharmacology · 2012Article
- Characterization and solubilization of pyrrole-imidazole polyamide aggregates.Journal of medicinal chemistry · 2012Article
- Microwave assisted synthesis of Py-Im polyamides.Organic letters · 2012Article
- Pharmacokinetics of Py-Im polyamides depend on architecture: cyclic versus linear.Journal of the American Chemical Society · 2012Article
- Enhancing the cellular uptake of Py-Im polyamides through next-generation aryl turns.Nucleic acids research · 2012Article
- Targeting a DNA binding motif of the EVI1 protein by a pyrrole-imidazole polyamide.Biochemistry · 2011Article
- Structural basis for cyclic Py-Im polyamide allosteric inhibition of nuclear receptor binding.Journal of the American Chemical Society · 2010Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
The characterization of a new class of pyrrole-imidazole hairpin polyamides with beta-amino-gamma-turn units for recognition of the DNA minor groove is reported. A library of eight hairpins containing ( R)- and ( S)-3,4-diaminobutyric acid (beta-amino-gamma-turn) has been synthesized, and the impact of the molecules on DNA-duplex stabilization was studied for comparison with the parent gamma-aminobutyric acid (gamma-turn) and standard ( R)-2,4-diaminobutyric acid (alpha-amino-gamma-turn)-linked eight-ring polyamides. For some, but not all, sequence compositions, melting temperature analyses have revealed that both enantiomeric forms of the beta-amino-gamma-turn increase the DNA-binding affinity of polyamides relative to the ( R)-alpha-amino-gamma-turn. The ( R)-beta-amine residue may be an attractive alternative for constructing hairpin polyamide conjugates. Biological assays have shown that ( R)-beta-amino-gamma-turn hairpins are able to inhibit androgen receptor-mediated gene expression in cell culture similar to hairpins bearing the standard ( R)-alpha-amino-gamma-turn, from which we infer they are cell-permeable.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.