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Selectins01:25

Selectins

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Cell adhesion is  an essential aspect of multicellularity. While stable cell interactions usually occur between cells of the same type, transient cell interactions occur between cells of different tissue types, such as between neutrophils and endothelial cells. Selectins are one class of cell adhesion molecules (CAMs) that bind carbohydrate ligands to form transient cell adhesion. They are rod-like proteins with a long extracellular part of variable length ending with the lectin domain,...
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Protein glycosylation starts in the ER lumen and continues in the Golgi apparatus. Glycosyltransferases catalyze the addition of sugar molecules or glycosylation of proteins. Usually, these enzymes add sugars to the hydroxyl groups of selected serine or threonine residues to form O-linked glycans or the amino groups of asparagine residues to form N-linked glycans. Different positions on the same polypeptide chain can contain differently linked glycans.
Multiple sugar molecules that may or may...
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Enhancing lectin recognition via precise fluorination: Man5 glycomimetics for targeting DC-SIGN.

Adrián Silva-Díaz1, Michel Thépaut2, Jonathan Ramírez-Cárdenas1

  • 1Instituto de Investigaciones Químicas (IIQ), CSIC - Universidad de Sevilla, Av. Américo Vespucio 49, Seville 41092, Spain.

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|March 19, 2026
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Summary

Researchers developed fluorinated glycomimetics to improve DC-SIGN binding. A specific Man5 derivative enhanced binding affinity, showing potential for targeting DC-SIGN interactions, including with the SARS-CoV-2 spike protein.

Keywords:
DC-SIGNFluorGlycomimeticLectin recognitionMannose

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Area of Science:

  • Carbohydrate Chemistry
  • Glycobiology
  • Medicinal Chemistry

Background:

  • High-mannose N-glycans are crucial DC-SIGN ligands but difficult to synthesize.
  • Developing effective glycomimetics is key for understanding and targeting lectin recognition.

Purpose of the Study:

  • To create accessible glycomimetics that enhance DC-SIGN recognition through precise fluorination.
  • To investigate the impact of selective fluorination on the binding affinity of Man5-based glycomimetics to DC-SIGN.

Main Methods:

  • Synthesis of four fluorinated Man5 derivatives with selective C-2 and/or C-6 substitution.
  • Biophysical evaluation including affinity measurements and binding epitope mapping (NMR).
  • Molecular dynamics (MD) simulations and Isothermal Titration Calorimetry (ITC) to analyze binding interactions and thermodynamics.

Main Results:

  • Fluorination at C-6 significantly increased binding affinity, while C-2 substitution decreased it.
  • The (6F,6F)-Man5 derivative demonstrated superior inhibitory potency against DC-SIGN, outperforming natural Man5 and Man9.
  • Fluorination enhanced binding through favorable enthalpic contributions, including polar interactions and desolvation.

Conclusions:

  • Selective fluorination is a powerful strategy for enhancing lectin ligand affinity.
  • Fluorinated Man5 glycomimetics show promise as potent agents for targeting DC-SIGN.
  • This approach can lead to novel therapeutics for DC-SIGN mediated diseases and viral infections, such as SARS-CoV-2.