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

Abed Saady, Georgia Malcolm, Matthew Fitzpatrick, Noel Pairault, Graham Tizzard, Soran Mohammed, Ali Tavassoli, Stephen Goldup

Research output: Contribution to journalArticlepeer-review

38 Downloads (Pure)

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
Article numbere202400344
Number of pages7
JournalAngewandte Chemie (International Edition)
Volume2024
Early online date26 Jan 2024
DOIs
Publication statusPublished - 6 Mar 2024

Bibliographical note

SMG thanks the ERC (Agreement no. 724987) and Leverhulme Trust (RPG-2020-399) for funding and the Royal Society for a Wolfson Research Fellowship (RSWF\FT\180010). A. Saady thanks the Council for Higher Education-Israel for a personal fellowship.

Keywords

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

Fingerprint

Dive into the research topics of 'A Platform Approach to Cleavable Macrocycles for the Controlled Disassembly of Mechanically Caged Molecules'. Together they form a unique fingerprint.

Cite this