A Platform Approach to Cleavable Macrocycles for the Controlled Disassembly of Mechanically Caged Molecules

Abed Saady, Georgia K. Malcolm, Matthew P. Fitzpatrick, Noel Pairault, Graham J. Tizzard, Soran Mohammed, Ali Tavassoli, Stephen M. Goldup

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Inspired by interlocked oligonucleotides, peptides and knotted proteins, synthetic systems where a macrocycle cages a bioactive species that is “switched on” by breaking the mechanical bond have been reported. However, to date, each example uses a bespoke chemical design. Here we present a platform approach to mechanically caged structures wherein a single macrocycle precursor is diversified at a late stage to include a range of trigger units that control ring opening in response to enzymatic, chemical, or photochemical stimuli. We also demonstrate that our approach is applicable to other classes of macrocycles suitable for rotaxane and catenane formation.

Original languageEnglish
JournalAngewandte Chemie - International Edition
Early online date26 Jan 2024
DOIs
StatePublished - 15 Apr 2024
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Keywords

  • crown ethers
  • macrocycles
  • mechanical bonds
  • prodrugs
  • rotaxanes

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