A High‐Affinity “Synthavidin” Receptor for Squaraine Dyes

Federica Balduzzi; Patrick Stewart; Soumen K. Samanta; Tiddo J. Mooibroek; Thomas Hoeg‐Jensen; Kejia Shi; Bradley D. Smith; Anthony P. Davis

doi:10.1002/anie.202314373

A High‐Affinity “Synthavidin” Receptor for Squaraine Dyes

Federica Balduzzi, Patrick Stewart, Soumen K. Samanta, Tiddo J. Mooibroek^*, Thomas Hoeg‐Jensen, Kejia Shi, Bradley D. Smith^*, Anthony P. Davis^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

4 Citations (Scopus)

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=10¹⁰ m⁻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.

Original language	English
Article number	e202314373
Number of pages	8
Journal	Angewandte Chemie International Edition
Volume	62
Issue number	48
Early online date	10 Oct 2023
DOIs	https://doi.org/10.1002/anie.202314373
Publication status	Published - 27 Nov 2023

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@article{6da2beaf36274c888a28993b7bf66fd5,

title = "A High‐Affinity “Synthavidin” Receptor for Squaraine Dyes",

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 Ka=1010 m−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.",

author = "Federica Balduzzi and Patrick Stewart and Samanta, {Soumen K.} and Mooibroek, {Tiddo J.} and Thomas Hoeg‐Jensen and Kejia Shi and Smith, {Bradley D.} and Davis, {Anthony P.}",

year = "2023",

month = nov,

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doi = "10.1002/anie.202314373",

language = "English",

volume = "62",

journal = "Angewandte Chemie International Edition",

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T1 - A High‐Affinity “Synthavidin” Receptor for Squaraine Dyes

AU - Balduzzi, Federica

AU - Stewart, Patrick

AU - Samanta, Soumen K.

AU - Mooibroek, Tiddo J.

AU - Hoeg‐Jensen, Thomas

AU - Shi, Kejia

AU - Smith, Bradley D.

AU - Davis, Anthony P.

PY - 2023/11/27

Y1 - 2023/11/27

N2 - 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 Ka=1010 m−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.

AB - 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 Ka=1010 m−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.

U2 - 10.1002/anie.202314373

DO - 10.1002/anie.202314373

M3 - Article (Academic Journal)

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SN - 1521-3773

VL - 62

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 48

M1 - e202314373

ER -

A High‐Affinity “Synthavidin” Receptor for Squaraine Dyes

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