Synthesis and biological applications of fluoro-modified nucleic acids

Fluorine at the C5 Position of 2′-Deoxyuridine Enhances Repair of a O 4 -Methyl Adduct by O 6 -Alkylguanine DNA Alkyltransferases

(2017) Lauralicia Sacre et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Selection of 2′-Fluoro-Modified Aptamers with Optimized Properties

(2017) Deepak Thirunavukarasu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Biological applications of xeno nucleic acids

(2017) Kunihiko Morihiro et al.   Molecular BioSystems

MicroRNA therapeutics: towards a new era for the management of cancer and other diseases

(2017) Rajesha Rupaimoole et al.   NATURE REVIEWS DRUG DISCOVERY

Characterization of human telomere RNA G-quadruplex structures in vitro and in living cells using 19F NMR spectroscopy

(2017) Hong-Liang Bao et al.   NUCLEIC ACIDS RESEARCH

Fluorocarbons Enhance Intracellular Delivery of Short STAT3-sensors and Enable Specific Imaging

(2017) Valeriy Metelev et al.   Theranostics

Chemical and structural modifications of RNAi therapeutics

(2016) Sook Hee Ku et al.   ADVANCED DRUG DELIVERY REVIEWS

Structural Basis for Excision of 5-Formylcytosine by Thymine DNA Glycosylase

(2016) Lakshmi S. Pidugu et al.   BIOCHEMISTRY

Limits of RNA 2′-OH Mimicry by Fluorine: Crystal Structure of Bacillus halodurans RNase H Bound to a 2′-FRNA:DNA Hybrid

(2016) Pradeep S. Pallan et al.   BIOCHEMISTRY

2′-(R)-Fluorinated mC, hmC, fC and caC triphosphates are substrates for DNA polymerases and TET-enzymes

(2016) A. S. Schröder et al.   CHEMICAL COMMUNICATIONS

Characterization of G-Quadruplex/Hairpin Transitions of RNAs by19F NMR Spectroscopy

(2016) Lotta Granqvist et al.   CHEMISTRY-A EUROPEAN JOURNAL

18F-Containing Positron Emission Tomography Probe Conjugation Methodology for Biologics as Specific Binders for Tumors

(2016) Kenji Arimitsu et al.   CURRENT TOPICS IN MEDICINAL CHEMISTRY

Versatility of chemically synthesized guide RNAs for CRISPR-Cas9 genome editing

(2016) Melissa L. Kelley et al.   JOURNAL OF BIOTECHNOLOGY

Evolution of thermophilic DNA polymerases for the recognition and amplification of C2ʹ-modified DNA

(2016) Tingjian Chen et al.   Nature Chemistry

Aptamers as targeted therapeutics: current potential and challenges

(2016) Jiehua Zhou et al.   NATURE REVIEWS DRUG DISCOVERY

Stabilization of i-motif structures by 2′-β-fluorination of DNA

(2016) Hala Abou Assi et al.   NUCLEIC ACIDS RESEARCH

Synthesis of (R)-Configured 2′-Fluorinated mC, hmC, fC, and caC Phosphoramidites and Oligonucleotides

(2016) Arne S. Schröder et al.   ORGANIC LETTERS

Synthesis of 19F nucleic acid–polymer conjugates as real-time MRI probes of biorecognition

(2016) Giovanna Sicilia et al.   Polymer Chemistry

Locked 2′-Deoxy-2′,4′-Difluororibo Modified Nucleic Acids: Thermal Stability, Structural Studies, and siRNA Activity

(2015) Saúl Martínez-Montero et al.   ACS Chemical Biology

Antisense oligonucleotides in therapy for neurodegenerative disorders

(2015) Melvin M. Evers et al.   ADVANCED DRUG DELIVERY REVIEWS

Ortho-Stabilized18F-Azido Click Agents and their Application in PET Imaging with Single-Stranded DNA Aptamers

(2015) Lu Wang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Synthesis of 3′-Fluoro-tRNA Analogues for Exploring Non-ribosomal Peptide Synthesis in Bacteria

(2015) Laura Iannazzo et al.   CHEMBIOCHEM

Expanding the Scope of 2′-SCF3Modified RNA

(2015) Lukas Jud et al.   CHEMISTRY-A EUROPEAN JOURNAL

Substituting CF2for O4′ in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions

(2015) Yevgen P. Yurenko et al.   CHEMISTRY-A EUROPEAN JOURNAL

19F-labeling of the adenine H2-site to study large RNAs by NMR spectroscopy

(2015) F. Sochor et al.   JOURNAL OF BIOMOLECULAR NMR

Synthesis and Properties of 6′-Fluoro-tricyclo-DNA

(2015) Michal Medvecky et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of Fluorophosphate Nucleotide Analogues and Their Characterization as Tools for 19F NMR Studies

(2015) Marek R. Baranowski et al.   JOURNAL OF ORGANIC CHEMISTRY

2′-O-[(4-CF3-triazol-1-yl)methyl] Uridine – A Sensitive 19F NMR Sensor for the Detection of RNA Secondary Structures

(2015) Lotta Granqvist et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis and Properties of 2′-Deoxy-2′,4′-difluoroarabinose-Modified Nucleic Acids

(2015) Saúl Martínez-Montero et al.   JOURNAL OF ORGANIC CHEMISTRY

2′-Fluorination of Tricyclo-DNA Controls Furanose Conformation and Increases RNA Affinity

(2015) Alena Istrate et al.   ORGANIC LETTERS

Synthesis and Duplex-Stabilizing Properties of FluorinatedN-Methanocarbathymidine Analogues Locked in the C3′-endoConformation

(2014) Michael E. Jung et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Measurement of chemical exchange between RNA conformers by 19F NMR

(2014) Caijie Zhao et al.   BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS

i-Motif DNA: Structure, stability and targeting with ligands

(2014) Henry A. Day et al.   BIOORGANIC & MEDICINAL CHEMISTRY

19F Magnetic Resonance Imaging (MRI): From Design of Materials to Clinical Applications

(2014) Ilaria Tirotta et al.   CHEMICAL REVIEWS

Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water

(2014) Ricardo Lucas et al.   JOURNAL OF ORGANIC CHEMISTRY

Rigid 2′,4′-Difluororibonucleosides: Synthesis, Conformational Analysis, and Incorporation into Nascent RNA by HCV Polymerase

(2014) Saúl Martínez-Montero et al.   JOURNAL OF ORGANIC CHEMISTRY

4′-C-[(4-Trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine as a Sensitive 19F NMR Sensor for the Detection of Oligonucleotide Secondary Structures

(2014) Lotta Granqvist et al.   JOURNAL OF ORGANIC CHEMISTRY

A 6′-Fluoro-Substituent in Bicyclo-DNA Increases Affinity to Complementary RNA Presumably by CF–HC Pseudohydrogen Bonds

(2014) Branislav Dugovic et al.   JOURNAL OF ORGANIC CHEMISTRY

Comparison of Duplex Stabilizing Properties of 2′-Fluorinated Nucleic Acid Analogues with Furanose and Non-Furanose Sugar Rings

(2014) Michael E. Østergaard et al.   JOURNAL OF ORGANIC CHEMISTRY

Surprising Base Pairing and Structural Properties of 2′-Trifluoromethylthio-Modified Ribonucleic Acids

(2014) Marija Košutić et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Backbone FCH⋅⋅⋅O Hydrogen Bonds in 2′F-Substituted Nucleic Acids

(2013) Nerea Martin-Pintado et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001–2011)

(2013) Jiang Wang et al.   CHEMICAL REVIEWS

Probing DNA Mismatched and Bulged Structures by Using19F NMR Spectroscopy and Oligodeoxynucleotides with an19F-Labeled Nucleobase

(2013) Kazuhito Tanabe et al.   CHEMISTRY-A EUROPEAN JOURNAL

Synthesis and Cytostatic and Antiviral Activities of 2′-Deoxy-2′,2′-difluororibo- and 2′-Deoxy-2′-fluororibonucleosides Derived from 7-(Het)aryl-7-deazaadenines

(2013) Pavla Perlíková et al.   ChemMedChem

Dramatic Effect of Furanose C2′ Substitution on Structure and Stability: Directing the Folding of the Human Telomeric Quadruplex with a Single Fluorine Atom

(2013) Nerea Martín-Pintado et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The Steric Hypothesis for DNA Replication and Fluorine Hydrogen Bonding Revisited in Light of Structural Data

(2012) Martin Egli   ACCOUNTS OF CHEMICAL RESEARCH

2′-Fluoro RNA Shows Increased Watson-Crick H-Bonding Strength and Stacking Relative to RNA: Evidence from NMR and Thermodynamic Data

(2012) Amritraj Patra et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

2′-SCF3Uridine-A Powerful Label for Probing Structure and Function of RNA by19F NMR Spectroscopy

(2012) Katja Fauster et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Synthesis, Duplex Stabilization and Structural Properties of a Fluorinated Carbocyclic LNA Analogue

(2012) Punit P. Seth et al.   CHEMBIOCHEM

Synthesis of Deoxynucleoside Triphosphates that Include Proline, Urea, or Sulfonamide Groups and Their Polymerase Incorporation into DNA

(2012) Marcel Hollenstein   CHEMISTRY-A EUROPEAN JOURNAL

Synthesis and Antisense Properties of Fluoro Cyclohexenyl Nucleic Acid (F-CeNA), a Nuclease Stable Mimic of 2′-Fluoro RNA

(2012) Punit P. Seth et al.   JOURNAL OF ORGANIC CHEMISTRY

Thymine DNA glycosylase specifically recognizes 5-carboxylcytosine-modified DNA

(2012) Liang Zhang et al.   Nature Chemical Biology

Unique motifs and hydrophobic interactions shape the binding of modified DNA ligands to protein targets

(2012) D. R. Davies et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

A Programmable Dual-RNA-Guided DNA Endonuclease in Adaptive Bacterial Immunity

(2012) M. Jinek et al.   SCIENCE

Synthetic Genetic Polymers Capable of Heredity and Evolution

(2012) V. B. Pinheiro et al.   SCIENCE

Synthesis of DNA oligos containing 2′-deoxy-2′-fluoro-d-arabinofuranosyl-5-carboxylcytosine as hTDG inhibitor

(2012) Qing Dai et al.   TETRAHEDRON

Unique Gene-Silencing and Structural Properties of 2′-Fluoro-Modified siRNAs

(2011) Muthiah Manoharan et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Insights from Crystal Structures into the Opposite Effects on RNA Affinity Caused by the S- and R-6′-Methyl Backbone Modifications of 3′-Fluoro Hexitol Nucleic Acid

(2011) Pradeep S. Pallan et al.   BIOCHEMISTRY

Enzymatic Recognition of 2′-Modified Ribonucleoside 5′-Triphosphates: Towards the Evolution of Versatile Aptamers

(2011) Lasse H. Lauridsen et al.   CHEMBIOCHEM

Silicon-Based Chemistry: An Original and Efficient One-Step Approach to [18F]-Nucleosides and [18F]-Oligonucleotides for PET Imaging

(2011) Jürgen Schulz et al.   CHEMISTRY-A EUROPEAN JOURNAL

Synthesis, Improved Antisense Activity and Structural Rationale for the Divergent RNA Affinities of 3′-Fluoro Hexitol Nucleic Acid (FHNA and Ara-FHNA) Modified Oligonucleotides

(2011) Martin Egli et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Inhibition of miR-33a/b in non-human primates raises plasma HDL and lowers VLDL triglycerides

(2011) Katey J. Rayner et al.   NATURE

Development of Double-Stranded siRNA Labeling Method Using Positron Emitter and Its In Vivo Trafficking Analyzed by Positron Emission Tomography

(2010) Kentaro Hatanaka et al.   BIOCONJUGATE CHEMISTRY

General Method for Labeling siRNA by Click Chemistry with Fluorine-18 for the Purpose of PET Imaging

(2010) Frédéric Mercier et al.   BIOCONJUGATE CHEMISTRY

Monitoring of duplex and triplex formation by 19F NMR using oligodeoxynucleotides possessing 5-fluorodeoxyuridine unit as 19F signal transmitter

(2010) Kazuhito Tanabe et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Click-Chemistry Reactions in Radiopharmaceutical Chemistry: Fast & Easy Introduction of Radiolabels into Biomolecules for In Vivo Imaging

(2010) C. Wangler et al.   CURRENT MEDICINAL CHEMISTRY

13C/15N−19F Intermolecular REDOR NMR Study of the Interaction of TAR RNA with Tat Peptides

(2010) Wei Huang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Characterization of RNA Invasion by19F NMR Spectroscopy

(2010) Anu Kiviniemi et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Energetically Important C−H···F−C Pseudohydrogen Bonding in Water: Evidence and Application to Rational Design of Oligonucleotides with High Binding Affinity

(2010) Maryam Yahyaee Anzahaee et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Aptamers as therapeutics

(2010) Anthony D. Keefe et al.   NATURE REVIEWS DRUG DISCOVERY

Unexpected origins of the enhanced pairing affinity of 2′-fluoro-modified RNA

(2010) Pradeep S. Pallan et al.   NUCLEIC ACIDS RESEARCH

Fluorocarbon oligonucleotide conjugates for nucleic acids delivery

(2010) Guilhem Godeau et al.   MedChemComm

Enzymatic synthesis of perfluoroalkylated DNA

(2009) Bastian Holzberger et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Exploring Chemical Modifications for siRNA Therapeutics: A Structural and Functional Outlook

(2009) Siddharth Shukla et al.   ChemMedChem

Synthesis and characterization of 2′-modified-4′-thioRNA: a comprehensive comparison of nuclease stability

(2009) Mayumi Takahashi et al.   NUCLEIC ACIDS RESEARCH

5-Fluoro pyrimidines: labels to probe DNA and RNA secondary structures by 1D 19 F NMR spectroscopy

(2009) Barbara Puffer et al.   NUCLEIC ACIDS RESEARCH

A large-scale chemical modification screen identifies design rules to generate siRNAs with high activity, high stability and low toxicity

(2009) Jesper B. Bramsen et al.   NUCLEIC ACIDS RESEARCH

Studies on the hydrolytic stability of 2′-fluoroarabinonucleic acid (2′F-ANA)

(2009) Jonathan K. Watts et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Recent advances in the synthesis of fluorinated nucleosides

(2009) Xiao-Long Qiu et al.   TETRAHEDRON

Targeting RNA with Small Molecules

(2008) Jason R. Thomas et al.   CHEMICAL REVIEWS

Steric Effects in RNA Interference: Probing the Influence of Nucleobase Size and Shape

(2008) Alvaro Somoza et al.   CHEMISTRY-A EUROPEAN JOURNAL

Fluorinated nucleosides: Synthesis and biological implication

(2008) Peng Liu et al.   JOURNAL OF FLUORINE CHEMISTRY

Recommendations on the Use of 18F-FDG PET in Oncology

(2008) J. W. Fletcher et al.   JOURNAL OF NUCLEAR MEDICINE

Synthesis and Structure of Duplex DNA Containing the Genotoxic Nucleobase Lesion N7-Methylguanine

(2008) Seongmin Lee et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

19F NMR Spectroscopy for the Analysis of RNA Secondary Structure Populations

(2008) Dagmar Graber et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

DNA with stable fluorinated dA and dG substitutes: syntheses, base pairing and 19F-NMR spectra of 7-fluoro-7-deaza-2′-deoxyadenosine and 7-fluoro-7-deaza-2′-deoxyguanosine

(2008) Frank Seela et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

A Nonafluoro Nucleoside as a Sensitive19F NMR Probe of Nucleic Acid Conformation

(2008) Nivrutti B. Barhate et al.   ORGANIC LETTERS

Fluorine in medicinal chemistry

(2007) Sophie Purser et al.   CHEMICAL SOCIETY REVIEWS