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Spiropyran-Based Photoisomerizable α-Amino Acid for Membrane-Active Peptide Modification.

Andrii Hrebonkin1,2, Sergii Afonin1, Anna Nikitjuka2,3

  • 1Karlsruhe Institute of Technology, POB 3640, 76021, Karlsruhe, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 17, 2024
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Summary

Researchers developed a novel spiropyran amino acid for photoisomerizable peptides. This advancement enables light-controlled regulation of peptide functions, including toxicity and biological activity, opening new avenues in photopharmacology.

Keywords:
BP100membrane-active peptidesmolecular photoswitchesphotopharmacologyspiropyran

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Area of Science:

  • Medicinal Chemistry
  • Biochemistry
  • Photopharmacology

Background:

  • Photoisomerizable peptides are key in photopharmacology.
  • Azobenzene and diarylethene peptides show promise.
  • Spiropyran use in photoregulating bioactive peptides is underexplored.

Purpose of the Study:

  • To design and synthesize a spiropyran-derived amino acid for photoisomerizable peptides.
  • To demonstrate the utility of this amino acid by incorporating it into a bioactive peptide.
  • To investigate the photoregulation of peptide functions.

Main Methods:

  • Synthesis of a novel spiropyran amino acid: (S)-2-amino-3-(6'-methoxy-1',3',3'-trimethylspiro-[2H-1-benzopyran-2,2'-indolin-6-yl])propanoic acid.
  • Incorporation of the spiropyran amino acid into the membrane-active peptide BP100.
  • Assessment of photoisomerization effects on peptide toxicity, bacteriotoxicity, and actin-auxin oscillator modulation.

Main Results:

  • Successful synthesis of a spiropyran-derived amino acid suitable for peptide preparation.
  • Demonstrated photoregulation of membrane perturbation by spiropyran-containing BP100.
  • Significant photoisomer-dependent modulation of peptide toxicity, bacteriotoxicity (E. coli), and actin-auxin oscillator activity.

Conclusions:

  • The novel spiropyran amino acid is a valuable building block for creating photoisomerizable peptides.
  • Spiropyran-based peptides offer light-controllable modulation of biological activities.
  • This work expands the toolkit for photopharmacology with spiropyran-based systems.