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Related Concept Videos

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Nucleophile-triggered prodrug release from polymer hydrogels.

Benjamin Klemm1, Magherita Tavasso1, Irene Piergentili1

  • 1Delft University of Technology, Department of Chemical Engineering Van der Maasweg 9 2629 HZ Delft The Netherlands R.Eelkema@tudelft.nl.

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Summary
This summary is machine-generated.

Researchers developed a novel prodrug strategy for dual-functionality, enabling signal-triggered drug release and polymer incorporation. This innovative approach shows promise for advanced drug delivery systems and targeted therapeutics.

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Area of Science:

  • Polymer Chemistry
  • Medicinal Chemistry
  • Bioconjugation

Background:

  • Tertiary amine-based prodrugs offer potential for controlled drug delivery.
  • Existing methods lack dual functionality for signal-triggered release and material incorporation.
  • Clickable azido-group units can facilitate covalent attachment to polymer scaffolds.

Purpose of the Study:

  • To develop a novel prodrug strategy with dual functionality for signal-triggered drug activation and covalent incorporation into polymer materials.
  • To demonstrate the versatility of the method using various amine drug candidates and biomarker nucleophiles.
  • To evaluate the efficacy of prodrug-loaded hydrogels in in vitro cancer models.

Main Methods:

  • Nucleophilic substitution reactions were employed to synthesize prodrugs on an azido-phenyl allyl bromide scaffold.
  • Drug activation was triggered by specific biomarker nucleophiles, including amino acids, neurotransmitters, and glutathione.
  • Hydrogel scaffolds were functionalized with prodrugs and tested in aqueous and cellular environments.

Main Results:

  • A variety of amine drug candidates were successfully converted into prodrugs.
  • Signal-triggered drug release was achieved using S or N-terminal biomarker nucleophiles.
  • In vitro studies demonstrated controlled drug release from hydrogel scaffolds, achieving ~100% wound closure inhibition in A549 lung cancer cells.

Conclusions:

  • The developed prodrug strategy enables dual functionality: signal-triggered activation and covalent incorporation into polymer materials.
  • This approach facilitates the creation of responsive prodrug-conjugate incorporated materials for advanced drug delivery.
  • The findings suggest significant potential for future advancements in specialized therapeutics and controlled release systems.