Synthesis of fluorinated thiodigalactoside analogues

Polyfluoroglycoside Synthesis via Simple Alkylation of an Anomeric Hydroxyl Group: Access to Fluoroetoposide Analogues

(2021) Thomas Tremblay et al.   JOURNAL OF ORGANIC CHEMISTRY

Recent progress and advanced technology in carbohydrate-based drug development

(2021) Lin Pan et al.   CURRENT OPINION IN BIOTECHNOLOGY

Protecting-Group-Free Synthesis of GB1107: An Orally Active Galectin-3 Antagonist

(2021) Denis Giguère et al.   SYNTHESIS-STUTTGART

Regioselective 3‐O‐Substitution of Unprotected Thiodigalactosides: Direct Route to Galectin Inhibitors

(2020) Pavla Bojarová et al.   CHEMISTRY-A EUROPEAN JOURNAL

Addressing the structural complexity of fluorinated glucose analogues: Insight into lipophilicities and solvation effects

(2020) Jacob St-Gelais et al.   CHEMISTRY-A EUROPEAN JOURNAL

The role of fluorine in glycomimetic drug design

(2020) Rachel Hevey   CHEMISTRY-A EUROPEAN JOURNAL

From Carbohydrates to Complex Organofluorines: Synthesis, Conformation, and Lipophilicity of Multivicinal‐Fluorine‐Containing Hexitol Analogues

(2020) Danny Lainé et al.   CHEMISTRY-A EUROPEAN JOURNAL

Fluorinated Carbohydrates as Lectin Ligands: Simultaneous Screening of a Monosaccharide Library and Chemical Mapping by 19F NMR Spectroscopy

(2020) J. Daniel Martínez et al.   JOURNAL OF ORGANIC CHEMISTRY

Stereoselective Synthesis of Fluorinated Galactopyranosides as Potential Molecular Probes for Galactophilic Proteins: Assessment of Monofluorogalactoside–LecA Interactions

(2019) Vincent Denavit et al.   CHEMISTRY-A EUROPEAN JOURNAL

Exploring the chemistry of non‐sticky sugars: Synthesis of polyfluorinated carbohydrate analogs of D‐allopyranose

(2019) Vincent Denavit et al.   CHEMISTRY-A EUROPEAN JOURNAL

Synthesis of Sialidase-Resistant Oligosaccharide and Antibody Glycoform Containing α2,6-Linked 3Fax-Neu5Ac

(2019) Hong-Jay Lo et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Synthesis and Lipophilicity of Trifluorinated Analogues of Glucose

(2019) Jacob St-Gelais et al.   JOURNAL OF ORGANIC CHEMISTRY

Unraveling Sugar Binding Modes to DC-SIGN by Employing Fluorinated Carbohydrates

(2019) J. Daniel Martínez et al.   MOLECULES

In Vivo Veritas: 18F-Radiolabeled Glycomimetics Allow Insights into the Pharmacological Fate of Galectin-3 Inhibitors

(2019) Klas Bratteby et al.   JOURNAL OF MEDICINAL CHEMISTRY

Thiodigalactoside–Bovine Serum Albumin Conjugates as High-Potency Inhibitors of Galectin-3: An Outstanding Example of Multivalent Presentation of Small Molecule Inhibitors

(2018) Hao Zhang et al.   BIOCONJUGATE CHEMISTRY

Dissecting the Structure–Activity Relationship of Galectin–Ligand Interactions

(2018) Yi-Chen Chan et al.   INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES

Systematic Tuning of Fluoro-galectin-3 Interactions Provides Thiodigalactoside Derivatives with Single-Digit nM Affinity and High Selectivity

(2018) Kristoffer Peterson et al.   JOURNAL OF MEDICINAL CHEMISTRY

Synthetic Inhibitors of Galectins: Structures and Syntheses

(2018) Vincent Denavit et al.   TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY

Designing interactions by control of protein–ligand complex conformation: tuning arginine–arene interaction geometry for enhanced electrostatic protein–ligand interactions

(2018) A.-L. Noresson et al.   Chemical Science

Aromatic heterocycle galectin-1 interactions for selective single-digit nM affinity ligands

(2018) Kristoffer Peterson et al.   RSC Advances

A Chiron approach towards the stereoselective synthesis of polyfluorinated carbohydrates

(2018) Vincent Denavit et al.   Nature Communications

Synthesis of Protected 3-Deoxy-3-fluoro- and 4-Deoxy-4-fluoro-d-galactopyranosides from Levoglucosan

(2017) Danny Lainé et al.   JOURNAL OF ORGANIC CHEMISTRY

Galectin-3-Binding Glycomimetics that Strongly Reduce Bleomycin-Induced Lung Fibrosis and Modulate Intracellular Glycan Recognition

(2016) Tamara Delaine et al.   CHEMBIOCHEM

A Selective Galactose–Coumarin-Derived Galectin-3 Inhibitor Demonstrates Involvement of Galectin-3-glycan Interactions in a Pulmonary Fibrosis Model

(2016) Vishal K. Rajput et al.   JOURNAL OF MEDICINAL CHEMISTRY

Dual thio-digalactoside-binding modes of human galectins as the structural basis for the design of potent and selective inhibitors

(2016) Tung-Ju Hsieh et al.   Scientific Reports

Applications of Fluorine in Medicinal Chemistry

(2015) Eric P. Gillis et al.   JOURNAL OF MEDICINAL CHEMISTRY

Antibody Recognition of Fluorinated Haptens and Antigens

(2014) Maximilian Reindl et al.   CURRENT TOPICS IN MEDICINAL CHEMISTRY

Design and Synthesis of Hydrolytically Stable Multivalent Ligands Bearing Thiodigalactoside Analogues for Peanut Lectin and Human Galectin-3 Binding

(2014) Alejandro J. Cagnoni et al.   JOURNAL OF ORGANIC CHEMISTRY

Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates

(2014) S. Mandal et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1

(2013) Hilde van Hattum et al.   JOURNAL OF MEDICINAL CHEMISTRY

When Galectins Recognize Glycans: From Biochemistry to Physiology and Back Again

(2011) Santiago Di Lella et al.   BIOCHEMISTRY

Inhibition of Galectins with Small Molecules

(2011) Christopher T. Öberg et al.   CHIMIA

1H-1,2,3-Triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors

(2010) Bader A. Salameh et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Fluorinated Carbohydrates as Lectin Ligands: Versatile Sensors in19F-Detected Saturation Transfer Difference NMR Spectroscopy

(2009) Tammo Diercks et al.   CHEMISTRY-A EUROPEAN JOURNAL

Galectin-Inhibitory Thiodigalactoside Ester Derivatives Have Antimigratory Effects in Cultured Lung and Prostate Cancer Cells

(2008) Tamara Delaine et al.   JOURNAL OF MEDICINAL CHEMISTRY

Understanding organofluorine chemistry. An introduction to the C–F bond

(2007) David O'Hagan   CHEMICAL SOCIETY REVIEWS

Fluorine in medicinal chemistry

(2007) Sophie Purser et al.   CHEMICAL SOCIETY REVIEWS