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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Because the DNA segments are cut and reorganized in a direction-specific manner, site-specific recombination has emerged as an efficient genetic engineering technique. Flippase and Cyclization recombinases or Flp and Cre, respectively, are two members of the tyrosine recombinase family derived from bacteriophages, that are used to mediate site-specific DNA insertions, deletions, and targeted expression of proteins in mammalian cell lines.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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The Synthesis of RGD-functionalized Hydrogels as a Tool for Therapeutic Applications
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Published on: October 7, 2016

Second generation specific-enzyme-activated rotaxane propeptides.

Antony Fernandes1, Aurélien Viterisi, Vincent Aucagne

  • 1School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, UK.

Chemical Communications (Cambridge, England)
|January 10, 2012
PubMed
Summary

This study developed a water-soluble rotaxane for peptide delivery. Glucosylated tetra(ethylene glycol) chains significantly enhanced solubility and allowed enzyme-triggered peptide release.

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Area of Science:

  • Supramolecular Chemistry
  • Bioconjugation Chemistry
  • Drug Delivery Systems

Background:

  • Rotaxanes offer unique structural properties for molecular applications.
  • Peptide-based therapeutics face challenges with stability and solubility.
  • Enzyme-cleavable linkers are crucial for targeted drug release.

Purpose of the Study:

  • To create a water-soluble rotaxane system for improved peptide delivery.
  • To investigate the impact of tetra(ethylene glycol) (TetEG) and glucosylated tetra(ethylene glycol) (Glc-TetEG) modifications on rotaxane solubility.
  • To demonstrate enzyme-triggered release of the parent peptide from the modified rotaxane.

Main Methods:

  • Synthesis of a peptidic rotaxane with a glycosidase-cleavable stopper.
  • Derivatization of the rotaxane with TetEG and Glc-TetEG chains via copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) 'click' reaction.
  • Solubility assessment of parent and derivatized rotaxanes in aqueous media.
  • Enzymatic cleavage studies using β-galactosidase to release the parent peptide.

Main Results:

  • The Glc-TetEG-derivatised rotaxane exhibited a >50,000-fold increase in aqueous solubility compared to the parent rotaxane.
  • The CuAAC 'click' reaction efficiently produced the water-soluble rotaxane conjugates.
  • The water-soluble rotaxane propeptide was effectively activated by β-galactosidase, releasing the parent peptide.

Conclusions:

  • TetEG and Glc-TetEG modifications render rotaxanes highly water-soluble.
  • Glucosylated rotaxanes provide a robust platform for enzyme-responsive peptide delivery.
  • This approach enhances the potential of rotaxanes in biomedical applications, particularly for peptide therapeutics.