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Synthesis of end-labeled multivalent ligands for exploring cell-surface-receptor-ligand interactions
E J Gordon1, J E Gestwicki, L E Strong
1Departments of Chemistry and Biochemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.
Chemistry & Biology
|February 9, 2000
Summary
Researchers developed a new method using ruthenium-initiated ring-opening metathesis polymerization (ROMP) to create functionalized polymers. These polymers specifically bind to cell surface L-selectin, offering potential for new anti-inflammatory materials.
Area of Science:
- Polymer Chemistry
- Biomaterials Science
- Chemical Biology
Background:
- Ring-opening metathesis polymerization (ROMP) is a versatile method for synthesizing novel materials.
- Ruthenium-initiated ROMP allows for the creation of biologically active polymers due to its functional group tolerance.
- Multivalent ligands targeting cell surface L-selectin were previously generated to inhibit inflammation.
Purpose of the Study:
- To investigate functionalized enol ethers as capping agents in ruthenium-initiated ROMP.
- To develop a general method for synthesizing multivalent materials with end-labels.
- To examine the specific, multivalent binding of ligands to L-selectin.
Main Methods:
- Synthesis of a bifunctional molecule for terminating ruthenium-initiated ROMP reactions.
- Utilizing an enol ether and a masked carboxylic acid for end-capping.
- Conjugation of a fluorescein derivative to an end-capped neoglycopolymer.
Main Results:
- A novel end-capping agent was synthesized for ruthenium-initiated ROMP.
- Fluorescence microscopy confirmed specific binding of neoglycopolymers to L-selectin on cells.
- Results indicate multivalent interactions mediate neoglycopolymers' binding to L-selectin.
Conclusions:
- Ruthenium-initiated ROMP enables the synthesis of biologically active, multivalent ligands with latent functional groups.
- Polymers can be labeled with diverse molecular tags (e.g., fluorescent molecules, biotin, antibodies).
- This strategy offers broad applications for conjugating reporter groups to ROMP polymers in material and biological sciences.