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Epidithiodiketopiperazines : strain-promoted thiol-mediated cellular uptake at the highest tension

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Published in ACS Central Science. 2017, vol. 3, no. 5, p. 449-453
Abstract The disulfide dihedral angle in epidithiodiketopiperazines (ETPs) is near 0°. Application of this highest possible ring tension to strain-promoted thiol-mediated uptake results in efficient delivery to the cytosol and nucleus. Compared to the previous best asparagusic acid (AspA), ring-opening disulfide exchange with ETPs occurs more efficiently even with nonactivated thiols, and the resulting thiols exchange rapidly with nonactivated disulfides. ETP-mediated cellular uptake is more than 20 times more efficient compared to AspA, occurs without endosomal capture, depends on temperature, and is “unstoppable” by inhibitors of endocytosis and conventional thiol-mediated uptake, including siRNA against the transferrin receptor. These results suggest that ETP-mediated uptake not only maximizes delivery to the cytosol and nucleus but also opens the door to a new multitarget hopping mode of action.
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Research groups Groupe Matile
Groupe Adibekian
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ZONG, Lili et al. Epidithiodiketopiperazines : strain-promoted thiol-mediated cellular uptake at the highest tension. In: ACS Central Science, 2017, vol. 3, n° 5, p. 449-453. https://archive-ouverte.unige.ch/unige:95404

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Deposited on : 2017-07-12

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