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Diselenolane-mediated cellular uptake

Hildebrandt, Jana
Weigand, Wolfgang
Published in Chemical Science. 2018, vol. 9, no. 7, p. 1860-1866
Abstract The emerging power of thiol-mediated uptake with strained disulfides called for a move from sulfur to selenium. We report that according to results with fluorescent model substrates, cellular uptake with 1,2-diselenolanes exceeds uptake with 1,2-dithiolanes and epidithiodiketopiperazines with regard to efficiency as well as intracellular localization. The diselenide analog of lipoic acid performs best. This 1,2-diselenolane delivers fluorophores efficiently to the cytosol of HeLa Kyoto cells, without detectable endosomal capture as with 1,2-dithiolanes or dominant escape into the nucleus as with epidithiodiketopiperazines. Diselenolane-mediated cytosolic delivery is non-toxic (MTT assay), sensitive to temperature but insensitive to inhibitors of endocytosis (chlorpromazine, methyl-β-cyclodextrin, wortmannin, cytochalasin B) and conventional thiol-mediated uptake (Ellman's reagent), and to serum. Selenophilicity, the extreme CSeSeC dihedral angle of 0° and the high but different acidity of primary and secondary selenols might all contribute to uptake. Thiol-exchange affinity chromatography is introduced as operational mimic of thiol-mediated uptake that provides, in combination with rate enhancement of DTT oxidation, direct experimental evidence for existence and nature of the involved selenosulfides.
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Research group Groupe Matile
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CHUARD, Nicolas et al. Diselenolane-mediated cellular uptake. In: Chemical Science, 2018, vol. 9, n° 7, p. 1860-1866. doi: 10.1039/C7SC05151D https://archive-ouverte.unige.ch/unige:102319

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Deposited on : 2018-02-20

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