Literature DB >> 25257803

Recognition of nucleic acid junctions using triptycene-based molecules.

Stephanie A Barros1, David M Chenoweth.   

Abstract

The modulation of nucleic acids by small molecules is an essential process across the kingdoms of life. Targeting nucleic acids with small molecules represents a significant challenge at the forefront of chemical biology. Nucleic acid junctions are ubiquitous structural motifs in nature and in designed materials. Herein, we describe a new class of structure-specific nucleic acid junction stabilizers based on a triptycene scaffold. Triptycenes provide significant stabilization of DNA and RNA three-way junctions, providing a new scaffold for the development of nucleic acid junction binders with enhanced recognition properties. Additionally, we report cytotoxicity and cell uptake data in two human ovarian carcinoma cell lines.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  DNA recognition; RNA recognition; nucleic acid recognition; triptycenes

Mesh:

Substances:

Year:  2014        PMID: 25257803      PMCID: PMC4265365          DOI: 10.1002/anie.201407061

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  78 in total

1.  Intramolecular DNA Coiling Mediated by a Metallo-Supramolecular Cylinder Support by the Leverhulme Trust (F/215/BC) and the EPSRC lifesciences interface network (GR/M91105) is gratefully acknowledged. Discussions with Julie MacPherson have been of great assistance during preparation of the manuscript.

Authors:  Michael J. Hannon; Virtudes Moreno; Maria J. Prieto; Erlend Moldrheim; Einar Sletten; Isabelle Meistermann; Christian J. Isaac; Karen J. Sanders; Alison Rodger
Journal:  Angew Chem Int Ed Engl       Date:  2001-03-02       Impact factor: 15.336

2.  Thermodynamic properties of an intramolecular DNA four-way junction.

Authors:  N Makube; H Klump; J Pikkemaat; C Altona
Journal:  Arch Biochem Biophys       Date:  1999-04-01       Impact factor: 4.013

3.  Solution structure of a DNA three-way junction containing two unpaired thymidine bases. Identification of sequence features that decide conformer selection.

Authors:  B N van Buuren; F J Overmars; J H Ippel; C Altona; S S Wijmenga
Journal:  J Mol Biol       Date:  2000-12-01       Impact factor: 5.469

4.  Helical junctions as determinants for RNA folding: origin of tertiary structure stability of the hairpin ribozyme.

Authors:  D Klostermeier; D P Millar
Journal:  Biochemistry       Date:  2000-10-24       Impact factor: 3.162

5.  Dissection of bacteriophage lambda site-specific recombination using synthetic peptide combinatorial libraries.

Authors:  G Cassell; M Klemm; C Pinilla; A Segall
Journal:  J Mol Biol       Date:  2000-06-23       Impact factor: 5.469

Review 6.  Molecular recognition of DNA by small molecules.

Authors:  P B Dervan
Journal:  Bioorg Med Chem       Date:  2001-09       Impact factor: 3.641

7.  Structural analysis of DNA replication fork reversal by RecG.

Authors:  M R Singleton; S Scaife; D B Wigley
Journal:  Cell       Date:  2001-10-05       Impact factor: 41.582

8.  Quasi-equivalence in site-specific recombinase structure and function: crystal structure and activity of trimeric Cre recombinase bound to a three-way Lox DNA junction.

Authors:  K C Woods; S S Martin; V C Chu; E P Baldwin
Journal:  J Mol Biol       Date:  2001-10-12       Impact factor: 5.469

9.  Interaction of three-way DNA junctions with steroids.

Authors:  T Kato; K Yano; K Ikebukuro; I Karube
Journal:  Nucleic Acids Res       Date:  2000-05-01       Impact factor: 16.971

Review 10.  Structures of helical junctions in nucleic acids.

Authors:  D M Lilley
Journal:  Q Rev Biophys       Date:  2000-05       Impact factor: 5.318

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  19 in total

1.  Increased Flexibility between Stems of Intramolecular Three-Way Junctions by the Insertion of Bulges.

Authors:  Carolyn E Carr; Luis A Marky
Journal:  Biophys J       Date:  2018-06-19       Impact factor: 4.033

2.  Modulation of the E. coli rpoH Temperature Sensor with Triptycene-Based Small Molecules.

Authors:  Stephanie A Barros; Ina Yoon; David M Chenoweth
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-30       Impact factor: 15.336

3.  Small Molecule Recognition Triggers Secondary and Tertiary Interactions in DNA Folding and Hammerhead Ribozyme Catalysis.

Authors:  Jie Mao; Chris DeSantis; Dennis Bong
Journal:  J Am Chem Soc       Date:  2017-07-13       Impact factor: 15.419

4.  Bridgehead-Substituted Triptycenes for Discovery of Nucleic Acid Junction Binders.

Authors:  Stephanie A Barros; Ina Yoon; Sung-Eun Suh; David M Chenoweth
Journal:  Org Lett       Date:  2016-05-12       Impact factor: 6.005

5.  Synthesis of 9-Substituted Triptycene Building Blocks for Solid-Phase Diversification and Nucleic Acid Junction Targeting.

Authors:  Ina Yoon; Sung-Eun Suh; Stephanie A Barros; David M Chenoweth
Journal:  Org Lett       Date:  2016-02-17       Impact factor: 6.005

6.  Context-Sensitive Cleavage of Folded DNAs by Loop-Targeting bPNAs.

Authors:  Yufeng Liang; Shiqin Miao; Jie Mao; Chris DeSantis; Dennis Bong
Journal:  Biochemistry       Date:  2020-06-23       Impact factor: 3.162

7.  Screening of Minimalist Noncanonical Sites in Duplex DNA and RNA Reveals Context and Motif-Selective Binding by Fluorogenic Base Probes.

Authors:  Yufeng Liang; Shiqin Miao; Jie Mao; Shekaraiah Devari; Maricarmen Gonzalez; Dennis Bong
Journal:  Chemistry       Date:  2021-11-24       Impact factor: 5.236

8.  Triptycene-based small molecules modulate (CAG)·(CTG) repeat junctions.

Authors:  Stephanie A Barros; David M Chenoweth
Journal:  Chem Sci       Date:  2015-06-10       Impact factor: 9.825

9.  Triple Aryne-Tetrazine Reaction Enabling Rapid Access to a New Class of Polyaromatic Heterocycles.

Authors:  Sung-Eun Suh; Stephanie A Barros; David M Chenoweth
Journal:  Chem Sci       Date:  2015       Impact factor: 9.825

10.  Hierarchical coassembly of DNA-triptycene hybrid molecular building blocks and zinc protoporphyrin IX.

Authors:  Rina Kumari; Sumit Singh; Mohan Monisha; Sourav Bhowmick; Anindya Roy; Neeladri Das; Prolay Das
Journal:  Beilstein J Nanotechnol       Date:  2016-05-12       Impact factor: 3.649

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