A Chalcogen-Bonding Cascade Switch for Planarizable Push–Pull Probes

Mariano Macchione, Antoine Goujon, Karolina Strakova, Heorhii V. Humeniuk, Giuseppe Licari, Emad Tajkhorshid, Naomi Sakai, Stefan Matile

Research output: Contribution to journalArticle

Abstract

Planarizable push–pull probes have been introduced to demonstrate physical forces in biology. However, the donors and acceptors needed to polarize mechanically planarized probes are incompatible with their twisted resting state. The objective of this study was to overcome this “flipper dilemma” with chalcogen-bonding cascade switches that turn on donors and acceptors only in response to mechanical planarization of the probe. This concept is explored by molecular dynamics simulations as well as chemical double-mutant cycle analysis. Cascade switched flipper probes turn out to excel with chemical stability, red shifts adding up to high significance, and focused mechanosensitivity. Most important, however, is the introduction of a new, general and fundamental concept that operates with non-trivial supramolecular chemistry, solves an important practical problem and opens a wide chemical space.

Original languageEnglish (US)
Pages (from-to)15752-15756
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number44
DOIs
StatePublished - Oct 28 2019

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Keywords

  • chalcogen bonds
  • fluorescent probes
  • force imaging
  • lipid bilayer membranes
  • push-pull fluorophores

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Macchione, M., Goujon, A., Strakova, K., Humeniuk, H. V., Licari, G., Tajkhorshid, E., Sakai, N., & Matile, S. (2019). A Chalcogen-Bonding Cascade Switch for Planarizable Push–Pull Probes. Angewandte Chemie - International Edition, 58(44), 15752-15756. https://doi.org/10.1002/anie.201909741