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Versatile Click Linker Enabling Native Peptide Release from Nanocarriers upon Redox Trigger.

Erik R Hebels1, Stefanie Dietl1, Matt Timmers1,2

  • 1Division of Pharmaceutics, Utrecht Institute for Pharmaceutical Sciences (UIPS), Utrecht University, Utrecht 3508 TB, The Netherlands.

Bioconjugate Chemistry
|December 11, 2023
PubMed
Summary
This summary is machine-generated.

We developed a novel linker for attaching therapeutic peptides to nanocarriers, enabling efficient drug delivery and release. This method improves peptide drug delivery and enhances tumor cell killing.

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Area of Science:

  • Bioconjugation Chemistry
  • Nanomedicine
  • Drug Delivery Systems

Background:

  • Nanocarriers enhance drug circulation, tumor uptake, and release kinetics.
  • Therapeutic peptides benefit from improved delivery strategies to increase their therapeutic index.
  • Orthogonal covalent linker chemistry is crucial for peptide synthesis, nanocarrier conjugation, and triggered release.

Purpose of the Study:

  • To develop a novel linker for conjugating therapeutic peptides to nanocarriers.
  • To facilitate on-the-resin peptide generation, nanocarrier conjugation, and triggered release of native peptides.
  • To investigate the efficacy of a new linker-peptide conjugate system for cancer therapy.

Main Methods:

  • Solid-phase peptide synthesis (SPPS) to conjugate a copper-free clickable linker (TMTHSI) to the oncolytic peptide LTX-315.
  • Attachment of the linker-peptide conjugate to azide-containing pegylated core-cross-linked polymeric micelles (CCPMs) via click chemistry.
  • In vitro release studies using glutathione and analysis of 1,6-elimination.
  • Cytotoxicity and cellular uptake studies using cell cultures.

Main Results:

  • A novel linker containing a strained alkyne, disulfide bond, and thiobenzyl carbamate spacer was synthesized and conjugated to LTX-315.
  • Hydrophilic linker-peptide conjugates were efficiently loaded onto 50 nm CCPMs under aqueous conditions (8 mass % loading, 56% efficiency).
  • In vitro studies showed rapid release of LTX-315 upon glutathione exposure, followed by 1,6-elimination, yielding the native peptide.
  • LTX-CCPMs demonstrated potent cytotoxicity against tumor cells, comparable to free LTX-315.

Conclusions:

  • A novel, orthogonal linker system enables efficient conjugation of therapeutic peptides to nanocarriers.
  • The developed nanocarrier system effectively delivers and releases therapeutic peptides, enhancing anti-cancer activity.
  • This approach offers a promising strategy for improving the therapeutic index of peptide-based drugs.