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Open Access Cellular Uptake Mediated by Cyclic Oligochalcogenides

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This article is Open Access under the terms of the Creative Commons CC BY-NC-ND licence.

Cellular uptake is one of the central challenges in chemical biology and beyond. With the objective to find conceptually innovative ways to enter into cells, cyclic oligochalcogenides (COCs) are emerging as powerful tools. Increasing ring tension is shown to maximize speed and selectivity of dynamic covalent exchange chemistry on the way into cells. However, simple dynamic covalent attachment immobilizes the transporters on membrane proteins, resulting in endosomal capture. To move across the membrane into the cytosol, dynamic covalent COC opening has to produce high acidity chalcogenols that remain deprotonated in neutral water and, according to the present working hypothesis, initiate COC walking along disulfide tracks in membrane proteins, across the bilayer and into the cytosol. Compatibility of diselenolanes, the current 'lord of the rings', with the delivery of larger substrates of biological relevance is currently under investigation.

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Keywords: CELLULAR UPTAKE; DYNAMIC COVALENT CHEMISTRY; MOLECULAR WALKERS; REACTIVE INTERMEDIATES

Document Type: Research Article

Affiliations: 1: Department of Organic Chemistry, University of Geneva, Geneva, Switzerland, SCS-DSM Award for best poster presentation in Medicinal Chemistry;, Email: [email protected] 2: Department of Organic Chemistry, University of Geneva, Geneva, Switzerland 3: Department of Organic Chemistry, University of Geneva, Geneva, Switzerland;, Email: [email protected]

Publication date: April 1, 2019

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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