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Issue 52, 2015
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Cellular uptake: lessons from supramolecular organic chemistry

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The objective of this Feature Article is to reflect on the importance of established and emerging principles of supramolecular organic chemistry to address one of the most persistent problems in life sciences. The main topic is dynamic covalent chemistry on cell surfaces, particularly disulfide exchange for thiol-mediated uptake. Examples of boronate and hydrazone exchange are added for contrast, comparison and completion. Of equal importance are the discussions of proximity effects in polyions and counterion hopping, and more recent highlights on ring tension and ion pair–π interactions. These lessons from supramolecular organic chemistry apply to cell-penetrating peptides, particularly the origin of “arginine magic” and the “pyrenebutyrate trick,” and the currently emerging complementary “disulfide magic” with cell-penetrating poly(disulfide)s. They further extend to the voltage gating of neuronal potassium channels, gene transfection, and the delivery of siRNA. The collected examples illustrate that the input from conceptually innovative chemistry is essential to address the true challenges in biology beyond incremental progress and random screening.

Graphical abstract: Cellular uptake: lessons from supramolecular organic chemistry

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Publication details

The article was received on 26 Apr 2015, accepted on 19 May 2015 and first published on 01 Jun 2015

Article type: Feature Article
DOI: 10.1039/C5CC03472H
Chem. Commun., 2015,51, 10389-10402

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    Cellular uptake: lessons from supramolecular organic chemistry

    G. Gasparini, E. Bang, J. Montenegro and S. Matile, Chem. Commun., 2015, 51, 10389
    DOI: 10.1039/C5CC03472H

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