Double threading through DNA: NMR structural study of a bis-naphthalene macrocycle bound to a thymine-thymine mismatch.

PubWeight™: 0.80‹?›

🔗 View Article (PMC 3367172)

Published in Nucleic Acids Res on February 22, 2012

Authors

Muriel Jourdan1, Anton Granzhan, Regis Guillot, Pascal Dumy, Marie-Paule Teulade-Fichou

Author Affiliations

1: CNRS UMR5250, ICMG FR2607, Département de Chimie Moléculaire, Université Joseph Fourier, 570 rue de la Chimie, 38041 Grenoble Cedex 9, France. muriel.jourdan@ujf-grenoble.fr

Articles cited by this

The DNA-damage response in human biology and disease. Nature (2009) 17.86

The CCPN data model for NMR spectroscopy: development of a software pipeline. Proteins (2005) 13.03

Thermodynamics and NMR of internal G.T mismatches in DNA. Biochemistry (1997) 7.33

DNA repair pathways as targets for cancer therapy. Nat Rev Cancer (2008) 6.69

DNA mismatch repair: functions and mechanisms. Chem Rev (2006) 6.03

Calculation of binding isotherms for heterogenous polymers. Biopolymers (1968) 4.26

Structure, dynamics, and energetics of deoxyguanosine . thymidine wobble base pair formation in the self-complementary d(CGTGAATTCGCG) duplex in solution. Biochemistry (1982) 3.76

A mechanistic perspective on the chemistry of DNA repair glycosylases. Chem Rev (2003) 2.84

Theoretical calculations of the helix-coil transition of DNA in the presence of large, cooperatively binding ligands. Biopolymers (1976) 2.26

Scanning of guanine-guanine mismatches in DNA by synthetic ligands using surface plasmon resonance. Nat Biotechnol (2001) 1.98

Isolation of a small molecule inhibitor of DNA base excision repair. Nucleic Acids Res (2005) 1.98

Evolution of poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors. From concept to clinic. J Med Chem (2010) 1.86

Detection of damaged DNA bases by DNA glycosylase enzymes. Biochemistry (2010) 1.76

Metallo-intercalators and metallo-insertors. Chem Commun (Camb) (2007) 1.70

Three-dimensional hydrogen-bond geometry and probability information from a crystal survey. J Comput Aided Mol Des (1996) 1.69

Insights into finding a mismatch through the structure of a mispaired DNA bound by a rhodium intercalator. Proc Natl Acad Sci U S A (2006) 1.55

Recognition of base mismatches in DNA by 5,6-chrysenequinone diimine complexes of rhodium(III): a proposed mechanism for preferential binding in destabilized regions of the double helix. Biochemistry (2000) 1.53

Human AP endonuclease 1 (APE1): from mechanistic insights to druggable target in cancer. Cancer Treat Rev (2010) 1.50

DNA mismatch-specific targeting and hypersensitivity of mismatch-repair-deficient cells to bulky rhodium(III) intercalators. Proc Natl Acad Sci U S A (2006) 1.48

Conformational transitions in thymidine bulge-containing deoxytridecanucleotide duplexes. Role of flanking sequence and temperature in modulating the equilibrium between looped out and stacked thymidine bulge states. J Biol Chem (1990) 1.45

A review of PARP inhibitors: from bench to bedside. Ann Oncol (2010) 1.41

Recognition of guanine-guanine mismatches by the dimeric form of 2-amino-1,8-naphthyridine. J Am Chem Soc (2001) 1.32

Identification and characterization of inhibitors of human apurinic/apyrimidinic endonuclease APE1. PLoS One (2009) 1.32

Structure and mechanism for DNA lesion recognition. Cell Res (2008) 1.30

How do DNA repair proteins locate damaged bases in the genome? Chem Biol (1997) 1.30

A rhodium(III) complex for high-affinity DNA base-pair mismatch recognition. Proc Natl Acad Sci U S A (2003) 1.30

Targeting poly(ADP-ribosyl)ation: a promising approach in cancer therapy. Trends Mol Med (2005) 1.29

Pyrimidine.pyrimidine base-pair mismatches in DNA. A nuclear magnetic resonance study of T.T pairing at neutral pH and C.C pairing at acidic pH in dodecanucleotide duplexes. J Mol Biol (1988) 1.29

Novel small-molecule inhibitor of apurinic/apyrimidinic endonuclease 1 blocks proliferation and reduces viability of glioblastoma cells. J Pharmacol Exp Ther (2010) 1.27

The DNA trackwalkers: principles of lesion search and recognition by DNA glycosylases. Mutat Res (2005) 1.26

Potent inhibition of human apurinic/apyrimidinic endonuclease 1 by arylstibonic acids. Mol Pharmacol (2007) 1.23

Small molecule inhibitors of DNA repair nuclease activities of APE1. Cell Mol Life Sci (2010) 1.21

Insertion of a bulky rhodium complex into a DNA cytosine-cytosine mismatch: an NMR solution study. J Am Chem Soc (2007) 1.21

DNA repair proteins as molecular targets for cancer therapeutics. Anticancer Agents Med Chem (2008) 1.17

Structure, dynamics, and thermodynamics of mismatched DNA oligonucleotide duplexes d(CCCAGGG)2 and d(CCCTGGG)2. Biochemistry (1987) 1.14

Solution conformation of an abasic DNA undecamer duplex d(CGCACXCACGC) x d(GCGTGTGTGCG): the unpaired thymine stacks inside the helix. Biochemistry (1997) 1.11

DNA mismatch repair in eukaryotes and bacteria. J Nucleic Acids (2010) 1.11

1H NMR determination of base-pair lifetimes in oligonucleotides containing single base mismatches. Nucleic Acids Res (2002) 1.11

A bulky rhodium complex bound to an adenosine-adenosine DNA mismatch: general architecture of the metalloinsertion binding mode. Biochemistry (2009) 1.10

DNA mismatch binding and antiproliferative activity of rhodium metalloinsertors. J Am Chem Soc (2009) 1.10

DNA repair: models for damage and mismatch recognition. Mutat Res (2000) 1.01

Solution structure of two mismatches A.A and T.T in the K-ras gene context by nuclear magnetic resonance and molecular dynamics. Eur J Biochem (1995) 0.99

Enhancing radiosensitivity: targeting the DNA repair pathways. Cancer Biol Ther (2009) 0.98

DNA mismatch-specific base flipping by a bisacridine macrocycle. Chembiochem (2003) 0.98

A macrocyclic bis-acridine shifts the equilibrium from duplexes towards DNA hairpins. Nucleic Acids Res (1997) 0.95

Inhibition of uracil DNA glycosylase by an oxacarbenium ion mimic. Biochemistry (2002) 0.93

The SPR sensor detecting cytosine[bond]cytosine mismatches. J Am Chem Soc (2004) 0.92

Targeting DNA repair pathways: a novel approach to reduce cancer therapeutic resistance. Cancer Treat Rev (2009) 0.90

Small-molecule ligand induces nucleotide flipping in (CAG)n trinucleotide repeats. Nat Chem Biol (2005) 0.89

Selective recognition of pyrimidine-pyrimidine DNA mismatches by distance-constrained macrocyclic bis-intercalators. Nucleic Acids Res (2008) 0.88

Solution structure of DAPI selectively bound in the minor groove of a DNA T.T mismatch-containing site: NMR and molecular dynamics studies. Nucleic Acids Res (1998) 0.87

Targeting DNA repair proteins for cancer treatment. Cell Mol Life Sci (2010) 0.86

Macrocyclic DNA-mismatch-binding ligands: structural determinants of selectivity. Chemistry (2010) 0.84

Threading bis-intercalation of a macrocyclic bisacridine at abasic sites in DNA: nuclear magnetic resonance and molecular modeling study. Biochemistry (1999) 0.84

Detection of guanine-adenine mismatches by surface plasmon resonance sensor carrying naphthyridine-azaquinolone hybrid on the surface. Nucleic Acids Res (2004) 0.83

Interaction of a macrocyclic bisacridine with DNA. Biochemistry (1990) 0.83

A pseudocatenane structure formed between DNA and A cyclic bisintercalator. J Am Chem Soc (2009) 0.82

Competitive inhibition of uracil DNA glycosylase by a modified nucleotide whose triphosphate is a substrate for DNA polymerase. J Am Chem Soc (2009) 0.81

Structure-specific binding of [Co(phen)(2)(HPIP)](3+) to a DNA duplex containing sheared G:A mismatch base pairs. J Inorg Biochem (2009) 0.77

DNA double helix destabilizing properties of cyclobisintercaland compounds and competition with a single strand binding protein. Bioorg Med Chem (2000) 0.76

Articles by these authors

A hitchhiker's guide to G-quadruplex ligands. Org Biomol Chem (2007) 2.27

Natural and pharmacological regulation of telomerase. Nucleic Acids Res (2002) 1.92

G-quadruplex-induced instability during leading-strand replication. EMBO J (2011) 1.77

Fluorescence-based melting assays for studying quadruplex ligands. Methods (2007) 1.38

Controlled density patterning of tolylterpyridine-tagged oligonucleotides. Langmuir (2011) 1.38

Chemoselective assembly and immunological evaluation of multiepitopic glycoconjugates bearing clustered Tn antigen as synthetic anticancer vaccines. Bioconjug Chem (2005) 1.36

G-quadruplex structures in TP53 intron 3: role in alternative splicing and in production of p53 mRNA isoforms. Carcinogenesis (2010) 1.34

Highly efficient G-quadruplex recognition by bisquinolinium compounds. J Am Chem Soc (2007) 1.34

Tumor targeting with RGD peptide ligands-design of new molecular conjugates for imaging and therapy of cancers. Anticancer Agents Med Chem (2007) 1.34

Template assembled cyclopeptides as multimeric system for integrin targeting and endocytosis. J Am Chem Soc (2004) 1.32

Reevaluation of telomerase inhibition by quadruplex ligands and their mechanisms of action. Proc Natl Acad Sci U S A (2007) 1.29

Genetic instability triggered by G-quadruplex interacting Phen-DC compounds in Saccharomyces cerevisiae. Nucleic Acids Res (2010) 1.26

In vivo optical imaging of integrin alphaV-beta3 in mice using multivalent or monovalent cRGD targeting vectors. Mol Cancer (2007) 1.17

Stabilization and structure of telomeric and c-myc region intramolecular G-quadruplexes: the role of central cations and small planar ligands. J Am Chem Soc (2007) 1.16

Rudimentary G-quadruplex-based telomere capping in Saccharomyces cerevisiae. Nat Struct Mol Biol (2011) 1.14

A G-quadruplex structure within the 5'-UTR of TRF2 mRNA represses translation in human cells. Nucleic Acids Res (2010) 1.13

Noninvasive optical imaging of ovarian metastases using Cy5-labeled RAFT-c(-RGDfK-)4. Mol Imaging (2006) 1.12

Clustering and internalization of integrin alphavbeta3 with a tetrameric RGD-synthetic peptide. Mol Ther (2009) 1.09

Exclusive platination of loop adenines in the human telomeric G-quadruplex. Org Biomol Chem (2009) 1.07

Towards a self-adjuvanting multivalent B and T cell epitope containing synthetic glycolipopeptide cancer vaccine. ChemMedChem (2008) 1.03

Multivalent glyco(cyclo)peptides. Chem Soc Rev (2012) 1.02

Antitumor activity of a self-adjuvanting glyco-lipopeptide vaccine bearing B cell, CD4+ and CD8+ T cell epitopes. Cancer Immunol Immunother (2008) 1.00

Multivalent RGD synthetic peptides as potent alphaVbeta3 integrin ligands. Org Biomol Chem (2006) 0.99

Specialization among iron-sulfur cluster helicases to resolve G-quadruplex DNA structures that threaten genomic stability. J Biol Chem (2013) 0.99

Properties of some variants of human beta2-microglobulin and amyloidogenesis. J Biol Chem (2003) 0.98

1-Ethoxyethylidene, a new group for the stepwise SPPS of aminooxyacetic acid containing peptides. J Org Chem (2008) 0.98

DNA mismatch-specific base flipping by a bisacridine macrocycle. Chembiochem (2003) 0.98

Linear and branched glyco-lipopeptide vaccines follow distinct cross-presentation pathways and generate different magnitudes of antitumor immunity. PLoS One (2010) 0.97

Visualizing the quadruplex: from fluorescent ligands to light-up probes. Top Curr Chem (2013) 0.97

The importance of metal geometry in the recognition of G-quadruplex-DNA by metal-terpyridine complexes. Org Biomol Chem (2007) 0.97

G-quartets assembly within a G-rich DNA flap. A possible event at the center of the HIV-1 genome. Nucleic Acids Res (2002) 0.97

New multifunctional molecular conjugate vector for targeting, imaging, and therapy of tumors. Mol Ther (2005) 0.96

In vivo imaging of tumour angiogenesis in mice with the alpha(v)beta (3) integrin-targeted tracer 99mTc-RAFT-RGD. Eur J Nucl Med Mol Imaging (2007) 0.96

A platinum-quinacridine hybrid as a G-quadruplex ligand. J Biol Inorg Chem (2007) 0.95

Hepatocyte targeting and intracellular copper chelation by a thiol-containing glycocyclopeptide. J Am Chem Soc (2010) 0.95

Oxime bond formation for the covalent attachment of oligonucleotides on glass support. Bioorg Med Chem Lett (2003) 0.94

G-quadruplex recognition by quinacridines: a SAR, NMR, and biological study. ChemMedChem (2007) 0.94

In vivo noninvasive optical imaging of receptor-mediated RGD internalization using self-quenched Cy5-labeled RAFT-c(-RGDfK-)(4). Mol Imaging (2007) 0.93

Engineering bisquinolinium/thiazole orange conjugates for fluorescent sensing of G-quadruplex DNA. Angew Chem Int Ed Engl (2009) 0.93

Development of a fluorescent intercalator displacement assay (G4-FID) for establishing quadruplex-DNA affinity and selectivity of putative ligands. Bioorg Med Chem Lett (2006) 0.93

In vivo molecular imaging of atherosclerotic lesions in ApoE-/- mice using VCAM-1-specific, 99mTc-labeled peptidic sequences. J Nucl Med (2013) 0.92

Oxime ligation: a chemoselective click-type reaction for accessing multifunctional biomolecular constructs. Chemistry (2013) 0.92

Solution structure of a G-quadruplex bound to the bisquinolinium compound Phen-DC(3). Angew Chem Int Ed Engl (2013) 0.92

Development of a high-throughput G4-FID assay for screening and evaluation of small molecules binding quadruplex nucleic acid structures. Anal Bioanal Chem (2011) 0.91

Plasmodium telomeric sequences: structure, stability and quadruplex targeting by small compounds. Chembiochem (2008) 0.90

Efficient suppression of gene expression by targeting 5'-UTR-based RNA quadruplexes with bisquinolinium compounds. Chembiochem (2011) 0.90

In vivo molecular imaging of myocardial angiogenesis using the alpha(v)beta3 integrin-targeted tracer 99mTc-RAFT-RGD. J Nucl Cardiol (2010) 0.90

DNA switches on the two-photon efficiency of an ultrabright triphenylamine fluorescent probe specific of AT regions. J Am Chem Soc (2013) 0.90

A metal-mediated conformational switch controls G-quadruplex binding affinity. Angew Chem Int Ed Engl (2008) 0.90

Selective recognition of pyrimidine-pyrimidine DNA mismatches by distance-constrained macrocyclic bis-intercalators. Nucleic Acids Res (2008) 0.88

3-nitro-3-deaza-2'-deoxyadenosine as a versatile photocleavable 2'-deoxyadenosine mimic. J Am Chem Soc (2004) 0.88

Chemical and biological evaluations of an (111)in-labeled RGD-peptide targeting integrin alpha(V) beta(3) in a preclinical tumor model. Cancer Biother Radiopharm (2008) 0.88

2'-deoxyribonolactone lesion produces G->A transitions in Escherichia coli. Nucleic Acids Res (2004) 0.88

Fluorescence intercalator displacement assay for screening G4 ligands towards a variety of G-quadruplex structures. Biochimie (2011) 0.88

Structure-based design of small peptide inhibitors of protein kinase CK2 subunit interaction. Biochem J (2007) 0.87

One-pot approach to well-defined biomolecular assemblies by orthogonal chemoselective ligations. Angew Chem Int Ed Engl (2009) 0.87

An acyclic oligoheteroaryle that discriminates strongly between diverse G-quadruplex topologies. Angew Chem Int Ed Engl (2011) 0.86

Inhibition of dicing of guanosine-rich shRNAs by quadruplex-binding compounds. Chembiochem (2008) 0.86

Activatable fluorescent probes for tumour-targeting imaging in live mice. ChemMedChem (2006) 0.85

A multimeric quinacrine conjugate as a potential inhibitor of Alzheimer's beta-amyloid fibril formation. Chembiochem (2008) 0.85

Improvement of porphyrins for G-quadruplex DNA targeting. Biochimie (2011) 0.85

Sequence-specific Methyltransferase-Induced Labelling (SMILing) of plasmid DNA for studying cell transfection. Bioorg Med Chem (2007) 0.85

Synthesis and biological characterisation of targeted pro-apoptotic peptide. Chembiochem (2008) 0.84

Chemoselectively template-assembled glycoconjugates as mimics for multivalent presentation of carbohydrates. Org Lett (2003) 0.84

Oligonucleotide sequential bis-conjugation via click-oxime and click-Huisgen procedures. J Org Chem (2010) 0.84

Vinyl-pyridinium triphenylamines: novel far-red emitters with high photostability and two-photon absorption properties for staining DNA. Chembiochem (2007) 0.84

Macrocyclic DNA-mismatch-binding ligands: structural determinants of selectivity. Chemistry (2010) 0.84

Template-assembled synthetic G-quadruplex (TASQ): a useful system for investigating the interactions of ligands with constrained quadruplex topologies. Chemistry (2010) 0.84

Positron emission tomography imaging of tumor angiogenesis and monitoring of antiangiogenic efficacy using the novel tetrameric peptide probe 64Cu-cyclam-RAFT-c(-RGDfK-)4. Angiogenesis (2012) 0.84

Nucleic acids targeted to drugs: SELEX against a quadruplex ligand. Biochimie (2011) 0.83

Electrochemically controlled adsorption of Fc-functionalized polymers on beta-CD-modified self-assembled monolayers. Langmuir (2010) 0.83

Control of amyloid beta-peptide protofibril formation by a designed template assembly. Angew Chem Int Ed Engl (2006) 0.83

"One ring to bind them all"-part I: the efficiency of the macrocyclic scaffold for g-quadruplex DNA recognition. J Nucleic Acids (2010) 0.83

Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations. Beilstein J Org Chem (2012) 0.83

Redox strategy for reversible attachment of biomolecules using bifunctional linkers. Chem Commun (Camb) (2011) 0.83

Ligand-induced conformational changes with cation ejection upon binding to human telomeric DNA G-quadruplexes. J Am Chem Soc (2015) 0.83

Synthetic strategies to derivatizable triphenylamines displaying high two-photon absorption. J Org Chem (2008) 0.83

Stimulation of ribosomal frameshifting by RNA G-quadruplex structures. Nucleic Acids Res (2013) 0.83

Preparation of a multitopic glycopeptide-oligonucleotide conjugate. Org Lett (2005) 0.83

A novel heterobifunctional linker for facile access to bioconjugates. Org Biomol Chem (2006) 0.82

Targeted delivery of activatable fluorescent pro-apoptotic peptide into live cells. Org Biomol Chem (2008) 0.82

The oxime bond formation as an efficient chemical tool for the preparation of 3',5'-bifunctionalised oligodeoxyribonucleotides. Bioorg Med Chem Lett (2004) 0.82

Alpha and beta L-Fucopyranosyl oxyamines: key intermediates for the preparation of fucose-containing glycoconjugates by oxime ligation. Carbohydr Res (2007) 0.82

Stabilization of the G-quadruplex at the VEGF IRES represses cap-independent translation. RNA Biol (2015) 0.82

Bisquinolinium compounds induce quadruplex-specific transcriptome changes in HeLa S3 cell lines. BMC Res Notes (2012) 0.82

Neomycin-capped aromatic platforms: quadruplex DNA recognition and telomerase inhibition. Org Biomol Chem (2006) 0.82

Model peptides based on the binding loop of the copper metallochaperone Atx1: selectivity of the consensus sequence MxCxxC for metal ions Hg(II), Cu(I), Cd(II), Pb(II), and Zn(II). Inorg Chem (2006) 0.81

A fluorescent bisanthracene macrocycle discriminates between matched and mismatch-containing DNA. Chemistry (2009) 0.81

Retracted Synthesis of multivalent glycoconjugates containing the immunoactive LELTE peptide: effect of glycosylation on cellular activation and natural killing by human peripheral blood mononuclear cells. J Am Chem Soc (2010) 0.81

Structural and folding dynamic properties of the T70N variant of human lysozyme. J Biol Chem (2003) 0.81

FRET templated by G-quadruplex DNA: a specific ternary interaction using an original pair of donor/acceptor partners. J Am Chem Soc (2006) 0.81

Application of click-click chemistry to the synthesis of new multivalent RGD conjugates. Org Biomol Chem (2010) 0.81

Telomere targeting with a new G4 ligand enhances radiation-induced killing of human glioblastoma cells. Mol Cancer Ther (2011) 0.81

Tetravalent glycocyclopeptide with nanomolar affinity to wheat germ agglutinin. Org Biomol Chem (2013) 0.81

Recognition of G-quadruplex DNA by triangular star-shaped compounds: with or without side chains? Chemistry (2011) 0.81