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Diselenolane-mediated cellular uptake.

Nicolas Chuard1, Amalia I Poblador-Bahamonde1, Lili Zong1

  • 1Department of Organic Chemistry , University of Geneva , Geneva , Switzerland . Email: stefan.matile@unige.ch ; http://www.unige.ch/sciences/chiorg/matile/ ; Tel: +41 22 379 6523.

Chemical Science
|April 21, 2018
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Summary
This summary is machine-generated.

Selenium compounds, specifically 1,2-diselenolanes, show superior cellular uptake efficiency compared to sulfur analogs. This novel selenium-mediated delivery targets the cytosol effectively and is non-toxic.

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Area of Science:

  • Biochemistry
  • Cell Biology
  • Medicinal Chemistry

Background:

  • Thiol-mediated uptake using strained disulfides has been a focus, prompting exploration of selenium alternatives.
  • Understanding cellular uptake mechanisms is crucial for targeted drug delivery and biological research.

Purpose of the Study:

  • To investigate and compare the cellular uptake efficiency of selenium-based compounds (1,2-diselenolanes) against sulfur-based analogs (1,2-dithiolanes and epidithiodiketopiperazines).
  • To determine the intracellular localization and mechanism of uptake for 1,2-diselenolanes.

Main Methods:

  • Utilized fluorescent model substrates to track cellular uptake in HeLa Kyoto cells.
  • Employed MTT assay for toxicity assessment and various inhibitors to probe uptake pathways (endocytosis, thiol-mediated uptake).
  • Introduced thiol-exchange affinity chromatography and DTT oxidation assays to study selenosulfide formation.

Main Results:

  • Cellular uptake of 1,2-diselenolanes significantly exceeded that of 1,2-dithiolanes and epidithiodiketopiperazines in both efficiency and intracellular localization.
  • The diselenide analog of lipoic acid demonstrated optimal performance, delivering fluorophores to the cytosol without endosomal capture or nuclear accumulation.
  • Diselenolane-mediated delivery was confirmed as non-toxic, temperature-sensitive, and independent of endocytosis or conventional thiol-mediated pathways.

Conclusions:

  • 1,2-Diselenolanes represent a highly efficient and targeted system for cytosolic delivery, outperforming traditional sulfur-based compounds.
  • The unique properties of selenium, including selenophilicity and specific dihedral angles, likely contribute to this enhanced uptake.
  • The study introduces a novel method (thiol-exchange affinity chromatography) to elucidate the mechanisms of selenosulfide involvement in cellular uptake.