Strong‐binding host–guest pairings in aqueous media have potential as “supramolecular glues” in biomedical techniques, complementing the widely‐used (strept)avidin‐biotin combination. We have previously found that squaraine dyes are bound very strongly by tetralactam macrocycles possessing anthracenyl units as cavity walls. Here we show that replacing the anthracenes with pentacyclic 5,7,12,14‐tetrahydro‐5,7,12,14‐tetraoxapentacene (TOP) units generates receptors which bind squaraines with increased affinities (around
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Abstract K a=1010m −1) and improved selectivities. Binding can be followed through changes to squaraine fluorescence and absorbance. The TOP units are easy to prepare and potentially variable, while the TOP‐based receptor shows improved photostability, both in itself and in complex with squaraines. The results suggest that this system could prove valuable in the further development of practical “synthavidin” chemistry. -
more » « less
Abstract Strong‐binding host–guest pairings in aqueous media have potential as “supramolecular glues” in biomedical techniques, complementing the widely‐used (strept)avidin‐biotin combination. We have previously found that squaraine dyes are bound very strongly by tetralactam macrocycles possessing anthracenyl units as cavity walls. Here we show that replacing the anthracenes with pentacyclic 5,7,12,14‐tetrahydro‐5,7,12,14‐tetraoxapentacene (TOP) units generates receptors which bind squaraines with increased affinities (around
K a=1010m −1) and improved selectivities. Binding can be followed through changes to squaraine fluorescence and absorbance. The TOP units are easy to prepare and potentially variable, while the TOP‐based receptor shows improved photostability, both in itself and in complex with squaraines. The results suggest that this system could prove valuable in the further development of practical “synthavidin” chemistry. -
We developed an epigenetically active, cooperative DNA binding transcription factor platform assisted by cucurbit[7]uril (CB7) host–guest modules. This new type of molecule termed ePIP–HoGu not only mimics the operation of transcription factors as a pair but also recruits the epigenetic modifier to a particular DNA locus.more » « less
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Abstract We report the synthesis and X‐ray crystal structure of a cucurbituril–triptycene chimeric receptor (
1 ). Host1 binds to guests typical of CB[6]–CB[8], but also binds to larger guests such as blue box (20 ) and the Fujita square (22 ). Intriguingly, the geometries of the1 ⋅20 and1 ⋅22 complexes blur the lines between host and guest in that both components fulfill both roles within each complex. The fluorescence output of1 is fully quenched by the formation of complexes with pyridinium‐derived guests. -
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Abstract We report the synthesis and X‐ray crystal structure of a cucurbituril–triptycene chimeric receptor (
1 ). Host1 binds to guests typical of CB[6]–CB[8], but also binds to larger guests such as blue box (20 ) and the Fujita square (22 ). Intriguingly, the geometries of the1 ⋅20 and1 ⋅22 complexes blur the lines between host and guest in that both components fulfill both roles within each complex. The fluorescence output of1 is fully quenched by the formation of complexes with pyridinium‐derived guests.
