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Novel pH-Sensitive Cyclic Peptides.

Dhammika Weerakkody1, Anna Moshnikova1, Naglaa Salem El-Sayed2,3,4

  • 1Department of Physics, University of Rhode Island, Kingston, RI 02881, US.

Scientific Reports
|August 13, 2016
PubMed
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New cyclic peptides target acidic tissues and deliver molecules into cells based on pH. The asymmetric peptide c[E4W5C] showed promising tumor targeting in mice.

Area of Science:

  • Biochemistry
  • Molecular Biology
  • Drug Delivery

Background:

  • pH-sensitive agents are crucial for targeted drug delivery.
  • Cyclic peptides offer unique structural properties for molecular interactions.

Purpose of the Study:

  • To synthesize and evaluate novel cyclic peptides as pH-sensitive agents.
  • To investigate their potential for targeting acidic tissues and intracellular delivery.
  • To elucidate their mechanism of action within cell membranes.

Main Methods:

  • Synthesis of cyclic peptides with varying tryptophan (W) and glutamic acid (E) residues.
  • Biophysical studies to determine membrane localization and mechanism.
  • In vitro translocation assays with a polar cargo molecule (amanitin).

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  • In vivo tumor targeting studies in mice using fluorescently-labeled peptides.

    • Main Results:

    • Cyclic peptides c[(WE)4WC] and c[E4W5C] translocated amanitin across lipid bilayers in a pH-dependent manner.
    • These peptides induced cell death in a pH- and concentration-dependent manner.
    • The asymmetric peptide c[E4W5C] demonstrated significant targeting of acidic 4T1 mammary tumors in mice (tumor-to-muscle ratio of 5.6 at 24 hours).
    • A pH-insensitive peptide c[R4W5C] showed no tumor targeting, confirming the pH-sensitivity mechanism.

    Conclusions:

    • A novel class of pH-sensitive cyclic peptides has been developed.
    • These peptides can be utilized for targeted delivery to acidic environments and intracellular delivery.
    • The asymmetric peptide c[E4W5C] shows potential as a tool for investigating or targeting acidic tissues, including tumors.