A Platform Approach to Cleavable Macrocycles for the Controlled Disassembly of Mechanically Caged Molecules |
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Authors: | Dr. Abed Saady Georgia K. Malcolm Dr. Matthew P. Fitzpatrick Dr. Noel Pairault Dr. Graham J. Tizzard Dr. Soran Mohammed Prof. Ali Tavassoli Prof. Stephen M. Goldup |
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Affiliation: | 1. School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT UK;2. School of Chemistry, University of Southampton, University Road, Southampton, SO17 1BJ UK |
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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. |
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Keywords: | mechanical bonds rotaxanes macrocycles crown ethers prodrugs |
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