Search results for "Quadruplex"

showing 10 items of 104 documents

Assessing the Differential Affinity of Small Molecules for Noncanonical DNA Structures

2012

The targeting of higher-order DNA structures has been thoroughly developed with G-quadruplex DNA but not with other structures like branched DNA (also known as DNA junctions). Because these alternative higher-order DNA architectures might be of high biological relevance, we implemented a high-throughput version of the FRET melting assay that enabled us to map the interactions of a candidate with four different DNA structures (duplex- and quadruplex DNA, three- and four-way junctions) in a rapid and reliable manner. We also introduce a novel index, the BONDS (branched and other noncanonical DNA selectivity) index, to conveniently quantify this differential affinity.

Models MolecularBase pairBiologyG-quadruplex01 natural sciencesBiochemistrySmall Molecule Libraries03 medical and health scienceschemistry.chemical_compoundCaffeineFluorescence Resonance Energy TransferAnticarcinogenic AgentsMolecular BiologyComputingMilieux_MISCELLANEOUS030304 developmental biology0303 health sciencesBase Sequence010405 organic chemistryOrganic ChemistrySmall Molecule LibrariesDNAMolecular biologySmall molecule0104 chemical sciencesG-Quadruplexes[SDV.BBM.BP]Life Sciences [q-bio]/Biochemistry Molecular Biology/BiophysicsQuadruplex DNAFörster resonance energy transferchemistryDuplex (building)BiophysicsNucleic Acid ConformationThermodynamicsMolecular MedicineOrganogold CompoundsDNAChemBioChem
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G-quadruplex vs. duplex-DNA binding of nickel(II) and zinc(II) Schiff base complexes

2016

Novel nickel(II) (1) and zinc(II) (2) complexes of a Salen-like ligand, carrying a pyrimidine ring on the N,N' bridge, were synthesized and characterized. Their interaction with duplex and G-quadruplex DNA was investigated in aqueous solution through UV-visible absorption, circular dichroism and viscometry measurements. The results obtained point out that, while the zinc(II) complex does not interact with both duplex and G-quadruplex DNA, the nickel(II) complex 1 binds preferentially to G-quadruplex respect to duplex-DNA, with values of the DNA-binding constants, Kb, 2.6×10(5)M(-1) and 3.5×10(4)M(-1), respectively. Molecular dynamics simulations provided an atomic level model of the top-sta…

Models MolecularCircular dichroismComputational chemistryInorganic chemistryBinding constantchemistry.chemical_elementZincCircular dichroism010402 general chemistryG-quadruplexDNA G-quadruplex nickel01 natural sciencesBiochemistryInorganic Chemistrychemistry.chemical_compoundNickelheterocyclic compoundsSchiff BasesSchiff base010405 organic chemistryOligonucleotidezincDNABinding constantSettore CHIM/08 - Chimica Farmaceutica0104 chemical sciencesG-QuadruplexesCrystallographyNickelchemistryDuplex (building)Settore CHIM/03 - Chimica Generale E Inorganica
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Template-Assembled Synthetic G-Quadruplex (TASQ): A Useful System for Investigating the Interactions of Ligands with Constrained Quadruplex Topologies

2010

A new biomolecular device for investigating the interactions of ligands with constrained DNA quadruplex topologies, using surface plasmon resonance (SPR), is reported. Biomolecular systems containing an intermolecular-like G-quadruplex motif 1 (parallel G-quadruplex conformation), an intramolecular G-quadruplex 2, and a duplex DNA 3 have been designed and developed. The method is based on the concept of template-assembled synthetic G-quadruplex (TASQ), whereby quadruplex DNA structures are assembled on a template that allows precise control of the parallel G-quadruplex conformation. Various known G-quadruplex ligands have been used to investigate the affinities of ligands for intermolecular…

Models MolecularDna duplexPorphyrinsStereochemistryOligonucleotides010402 general chemistryG-quadruplexLigands01 natural sciencesCatalysischemistry.chemical_compoundStructure-Activity Relationship[CHIM.ANAL]Chemical Sciences/Analytical chemistry[CHIM]Chemical SciencesComputer SimulationBinding siteSurface plasmon resonancePromoter Regions GeneticNuclear Magnetic Resonance BiomolecularComputingMilieux_MISCELLANEOUSBinding SitesMolecular Structure010405 organic chemistryChemistryOrganic ChemistryGeneral ChemistryDNASurface Plasmon ResonanceAffinities0104 chemical sciencesQuadruplex DNAG-QuadruplexesIntramolecular forceNucleic Acid Conformation[ CHIM.ANAL ] Chemical Sciences/Analytical chemistryDNA
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DOTASQ as a prototype of nature-inspired G-quadruplex ligand

2011

DOTASQ (for DOTA-templated Synthetic G-quartet) is the first prototype of nature-inspired G-quadruplex ligand: its design, founded on a possible intramolecular G-quartet formation, enables it to interact with G-quadruplex DNA via an unprecedented nature-mimicking binding mode, based on the association between two G-quartets, one being native (quadruplex) and the other one artificial (ligand).

Models MolecularGuanineMacrocyclic CompoundsStereochemistryAntineoplastic AgentsLigands010402 general chemistryG-quadruplex01 natural sciencesCatalysischemistry.chemical_compoundMaterials ChemistryHumans[CHIM]Chemical SciencesNature inspiredTerbiumComputingMilieux_MISCELLANEOUSBinding SitesFourier Analysis010405 organic chemistryMetals and AlloysGeneral ChemistryLigand (biochemistry)0104 chemical sciencesSurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialsG-QuadruplexeschemistryMolecular ProbesIntramolecular forceCeramics and CompositesNucleic Acid ConformationHydrophobic and Hydrophilic InteractionsDNA
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Structure and Dynamics of RNA Guanine Quadruplexes in SARS-CoV-2 Genome. Original Strategies against Emerging Viruses

2021

Guanine quadruplex (G4) structures in the viral genome have a key role in modulating viruses' biological activity. While several DNA G4 structures have been experimentally resolved, RNA G4s are definitely less explored. We report the first calculated G4 structure of the RG-1 RNA sequence of SARS-CoV-2 genome, obtained by using a multiscale approach combining quantum and classical molecular modeling and corroborated by the excellent agreement between the corresponding calculated and experimental circular dichroism spectra. We prove the stability of the RG-1 G4 arrangement as well as its interaction with G4 ligands potentially inhibiting viral protein translation.

Models MolecularLetterMolecular modelSARS-CoV-2ChemistryViral proteinGuanineCOVID-19RNATranslation (biology)Genome ViralComputational biologymedicine.disease_causeG-quadruplexGenomeG-Quadruplexeschemistry.chemical_compoundSettore CHIM/03 - Chimica Generale E InorganicamedicineHumansNucleic Acid ConformationRNA ViralGeneral Materials SciencePhysical and Theoretical ChemistryDNAThe Journal of Physical Chemistry Letters
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Porphyrin-Based Design of Bioinspired Multitarget Quadruplex Ligands

2014

Secondary nucleic acid structures, such as DNA and RNA quadruplexes, are potential targets for cancer therapies. Ligands that interact with these targets could thus find application as anticancer agents. Synthetic G-quartets have recently found numerous applications, including use as bioinspired G-quadruplex ligands. Herein, the design, synthesis and preliminary biophysical evaluation of a new prototype multitarget G-quadruplex ligand, (PNA)PorphySQ, are reported, where peptidic nucleic acid guanine ((PNA)G) was incorporated in the porphyrin-templated synthetic G-quartet (PorphySQ). Using fluorescence resonance energy transfer (FRET)-melting experiments, PorphySQ was shown to possess enhanc…

Models MolecularPeptide Nucleic AcidsGuaninePorphyrinsStereochemistryGuanineLigands010402 general chemistryG-quadruplex01 natural sciencesBiochemistryStructure-Activity Relationship03 medical and health scienceschemistry.chemical_compoundDrug Discovery[CHIM]Chemical SciencesStructure–activity relationshipheterocyclic compoundsGeneral Pharmacology Toxicology and PharmaceuticsBinding siteComputingMilieux_MISCELLANEOUS030304 developmental biologyPharmacology0303 health sciencesBinding SitesChemistryLigandOrganic ChemistryDNA0104 chemical sciencesG-QuadruplexesFörster resonance energy transferNucleic acidNucleic Acid ConformationRNAMolecular MedicineDNAChemMedChem
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Identifying three-way DNA junction-specific small-molecules

2012

Three-way junction DNA (TWJ-DNA, also known as 3WJ-DNA) is an alternative secondary DNA structure comprised of three duplex-DNAs that converge towards a single point, termed the branch point. This point is characterized by unique geometrical properties that make its specific targeting by synthetic small-molecules possible. Such a targeting has already been demonstrated in the solid state but not thoroughly biophysically investigated in solution. Herein, a set of simple biophysical assays has been developed to identify TWJ-specific small-molecule ligands; these assays, inspired by the considerable body of work that has been reported to characterize the interactions between small-molecules an…

Models MolecularPorphyrinsSolid-stateNanotechnologyComputational biology010402 general chemistryLigands01 natural sciencesBiochemistrySmall Molecule Libraries03 medical and health scienceschemistry.chemical_compoundPiperidinesFluorescence Resonance Energy TransferTransition TemperatureComputingMilieux_MISCELLANEOUS030304 developmental biology0303 health sciencesAza CompoundsSpectrum AnalysisGeneral MedicineDNASmall moleculePorphyrin0104 chemical sciencesG-QuadruplexesSolutions[SDV.BBM.BP]Life Sciences [q-bio]/Biochemistry Molecular Biology/BiophysicsKineticschemistryMetalsThree wayQuinolinesThermodynamicsSingle pointDNA
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Recognition of G-quadruplex DNA by triangular star-shaped compounds: with or without side chains?

2011

International audience; We report the synthesis of two new series of triangular aromatic platforms, either with three aminoalkyl side chains (triazatrinaphthylene series, TrisK: six compounds), or without side chains (triazoniatrinaphthylene, TrisQ). The quadruplex-DNA binding behavior of the two series, which differ essentially by the localization of the cationic charges, was evaluated by means of FRET-melting and G4-FID assays. For the trisubstituted triazatrinaphthylenes (TrisK), the length of the substituents and the presence of terminal hydrogen-bond-donor groups (NH(2)) were shown to be crucial for ensuring a high quadruplex affinity (ΔT(1/2) values of up to 20 °C at 1 μM for the best…

Models MolecularStereochemistryIonic bonding010402 general chemistryG-quadruplexLigands01 natural sciencesCatalysischemistry.chemical_compoundStructure-Activity RelationshipHeterocyclic Compounds[CHIM] Chemical SciencesSide chainMoleculeStructure–activity relationship[CHIM]Chemical SciencesComputingMilieux_MISCELLANEOUSMolecular Structure010405 organic chemistryHydrogen bond[CHIM.ORGA]Chemical Sciences/Organic chemistryOrganic ChemistryGeneral Chemistry0104 chemical sciencesG-QuadruplexeschemistryAcridinesSelectivityAzo CompoundsDNAChemistry (Weinheim an der Bergstrasse, Germany)
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On the Mechanism of Gold/NHC Compounds Binding to DNA G-Quadruplexes: Combined Metadynamics and Biophysical Methods

2018

The binding modes and free-energy landscape of two AuI /N-heterocyclic carbene complexes interacting with G-quadruplexes, namely a human telomeric (hTelo) and a promoter sequence (C-KIT1), are studied here for the first time by metadynamics. The theoretical results are validated by FRET DNA melting assays and provide an accurate estimate of the absolute gold complex/DNA binding free energy. This advanced in silico approach is valuable to achieve rational drug design of selective G4 binders.

Molecular Structure010405 organic chemistryIn silicoMetadynamicsDrug designSequence (biology)General MedicineDNAGeneral Chemistryanticancer010402 general chemistryG-quadruplex01 natural sciencesCombinatorial chemistryCatalysis0104 chemical sciencesG-Quadruplexeschemistry.chemical_compoundNucleic acid thermodynamicsFörster resonance energy transferchemistryFluorescence Resonance Energy TransferN-heterocyclic carbenesGoldDNAAngewandte Chemie International Edition
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Synthesis of Azole-Heterocycles as Potential Antitumor and/or Antiviral Agents

2014

NNRTIantitumor agentoxazoleG-quadruplex ligandisoindolo[12-d][15]benzoxazepinetriazolesSettore CHIM/08 - Chimica Farmaceutica
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