TY - JOUR
T1 - A Platform Approach to Cleavable Macrocycles for the Controlled Disassembly of Mechanically Caged Molecules
AU - Saady, Abed
AU - Malcolm, Georgia K.
AU - Fitzpatrick, Matthew P.
AU - Pairault, Noel
AU - Tizzard, Graham J.
AU - Mohammed, Soran
AU - Tavassoli, Ali
AU - Goldup, Stephen M.
N1 - Publisher Copyright:
© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
PY - 2024
Y1 - 2024
N2 - 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.
AB - 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.
KW - crown ethers
KW - macrocycles
KW - mechanical bonds
KW - prodrugs
KW - rotaxanes
UR - http://www.scopus.com/inward/record.url?scp=85186568815&partnerID=8YFLogxK
U2 - 10.1002/anie.202400344
DO - 10.1002/anie.202400344
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AN - SCOPUS:85186568815
SN - 1433-7851
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
ER -