ArticleOrganic & biomolecular chemistry2009
Recognition and discrimination of DNA quadruplexes by acridine-peptide conjugates.
Article in Organic & biomolecular chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- G4-Ligand-Conjugated Oligonucleotides Mediate Selective Binding and Stabilization of Individual G4 DNA Structures.Journal of the American Chemical Society · 2024Article
- G-Quadruplexes in the Viral Genome: Unlocking Targets for Therapeutic Interventions and Antiviral Strategies.Viruses · 2023Review
- Selective targeting of mutually exclusive DNA G-quadruplexes: HIV-1 LTR as paradigmatic model.Nucleic acids research · 2020Article
- Developing Novel G-Quadruplex Ligands: from Interaction with Nucleic Acids to Interfering with Nucleic Acid⁻Protein Interaction.Molecules (Basel, Switzerland) · 2019Review
- Medicinal chemistry of acridine and its analogues.MedChemComm · 2018Review
- G4LDB: a database for discovering and studying G-quadruplex ligands.Nucleic acids research · 2013Article
- Beyond DNA binding - a review of the potential mechanisms mediating quinacrine's therapeutic activities in parasitic infections, inflammation, and cancers.Cell communication and signaling : CCS · 2011Article
- Targeting the c-Kit Promoter G-quadruplexes with 6-Substituted Indenoisoquinolines.ACS medicinal chemistry letters · 2010Article
- "One ring to bind them all"-part I: the efficiency of the macrocyclic scaffold for g-quadruplex DNA recognition.Journal of nucleic acids · 2010Article
- Molecular models for intrastrand DNA G-quadruplexes.BMC structural biology · 2009Article
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Authors and funding
7 authors.
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Abstract
We have explored a series of trisubstituted acridine-peptide conjugates for their ability to recognize and discriminate between DNA quadruplexes derived from the human telomere, and the c-kit and N-ras proto-oncogenes. Quadruplex affinity was measured as the peptide sequences were varied, together with their substitution position on the acridine, and the identity of the C-terminus (acid or amide). Surface plasmon resonance measurements revealed that all compounds bound to the human telomeric quadruplex with sub-micromolar affinity. Docking calculations from molecular modelling studies were used to model the effects of substituent orientation and peptide sequence. Modelling and experiment were in agreement that placement of the peptide over the face of the acridine is detrimental to binding affinity. The highest degrees of selectivity were observed towards the N-ras quadruplex by compounds capable of forming simultaneous contacts with their acridine and peptide moieties. The ligands that bound best displayed quadruplex affinities in the 1-5 nM range and at least 10-fold discrimination between the quadruplexes studied.
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