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Synthesis of Differentially Halogenated Lissoclimide Analogues To Probe Ribosome E-Site Binding.

Salvatore Terrosu1, Liliia Nurullina1, Nantamon Supantanapong2

  • 1INSERM U964, CNRS UMR7104, Université de Strasbourg, Institut de Génétique et de Biologie Moléculaire et Cellulaire (IGBMC), 67404 Illkirch, France.

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Marine-derived halogenated compounds, like lissoclimides, show potent biological activity. This study reveals that C2-halogen and C7-hydroxyl groups are critical for lissoclimide potency by enhancing ribosome binding and translation inhibition.

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Area of Science:

  • Marine Natural Products Chemistry
  • Medicinal Chemistry
  • Molecular Biology

Background:

  • Halogenated marine natural products, particularly lissoclimides, are known for their significant antimicrobial and anticancer properties.
  • Previous research identified a halogen-π dispersion interaction involving chlorolissoclimide and the ribosome's tRNA exit site.

Purpose of the Study:

  • To synthesize and evaluate lissoclimide analogues with varying C2 substituents (fluoro, bromo, methyl) to understand the role of halogen identity in biological activity.
  • To investigate the impact of these analogues on eukaryotic translational machinery and ribosome binding.

Main Methods:

  • Synthesis of fluorolissoclimide, bromolissoclimide, and methyllissoclimide analogues.
  • X-ray cocrystallography to determine structures of analogues bound to the eukaryotic ribosome.
  • In vitro and in vivo assays to assess effects on translation, ribosomal thermal stability, and binding constants (FRET).

Main Results:

  • Detailed structural insights into how lissoclimide analogues bind to the eukaryotic ribosome, interacting with ribosomal protein eL42.
  • Demonstrated that the C2-halogen atom, through a halogen-π interaction, synergizes with the C7-hydroxyl group's hydrogen bond to eL42.
  • Observed that this synergy leads to enhanced translation inhibition and cytotoxicity, with reduced activity in analogues lacking these key groups.

Conclusions:

  • The C2-halogen and C7-hydroxyl groups are essential for the potent biological activity of lissoclimides.
  • The halogen-π interaction at C2 and hydrogen bonding at C7 are critical for strong binding to the ribosome and effective translation inhibition.
  • This study provides a deeper understanding of the structure-activity relationships of lissoclimides, guiding future drug design.