Oligomers of Cyclic Oligochalcogenides for Enhanced Cellular Uptake

Article Article scientifique Article Oligomers of Cyclic Oligochalcogenides for Enhanced Cellular Uptake eng 2021 author Martinent Rémi 885155 author Du Dongchen 924798 author Lopez Andarias Javier 810949 author Sakai Naomi 0000-0002-9460-1944 131140 author Matile Stefan 0000-0002-8537-8349 129654 253-259 10.1002/cbic.202000630 1439-4227 Monomeric cyclic oligochalcogenides (COCs) are emerging as attractive transporters to deliver substrates of interest into the cytosol through thiol‐mediated uptake. The objective of this study was to explore COC oligomers. We report a systematic evaluation of monomers, dimers, and trimers of asparagusic, lipoic, and diselenolipoic acid as well as their supramolecular monomers, dimers, trimers, and tetramers. COC dimers were more than twice as active as the monomers on both the covalent and noncovalent levels, whereas COC trimers were not much better than dimers. These trends might suggest that thiol‐mediated uptake of COCs is synergistic over both short and long distances, that is, it involves more than two COCs and more than one membrane protein, although other interpretations cannot be excluded at this level of complexity. These results thus provide attractive perspectives for structural evolution as well as imminent use in practice. Moreover, they validate automated HC‐CAPA as an invaluable method to collect comprehensive data on cytosolic delivery within a reasonable time at a level of confidence that is otherwise inconceivable. Dewey 540 36 Département de chimie organique 141 false 761 Groupe Matile ChemBioChem 22 1 d480a6d7-3f2f-4ab4-9590-b14b9f68ad2f Article (Published version) Restricted cbic.202000630.pdf 3213740 application/pdf eaf1fb53-0fdd-4bae-9ad5-aabc37d3033e Article (Published version) Public 330.pdf 3557237 application/pdf openAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Oligomers of Cyclic Oligochalcogenides for Enhanced Cellular Uptake	ChemBioChem			2021	393	442

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Du, Dongchen