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A High-Affinity "Synthavidin" Receptor for Squaraine Dyes.

Federica Balduzzi¹, Patrick Stewart¹, Soumen K Samanta¹

¹School of Chemistry, University of Bristol, Cantock's Close, Bristol, United Kingdom.

Angewandte Chemie (International Ed. in English)

|October 10, 2023

Summary

New supramolecular glues, based on tetralactam macrocycles with pentacyclic tetraoxapentacene (TOP) units, show enhanced binding affinities and selectivities for squaraine dyes. This advance offers a promising alternative to avidin-biotin systems in biomedical applications.

Keywords:

Fluorescent Probes High-Affinity Binding Host-Guest Systems Molecular Recognition Synthavidin

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Area of Science:

Supramolecular Chemistry
Organic Chemistry
Biomedical Engineering

Background:

Strong host-guest interactions are crucial for supramolecular chemistry, with applications as "supramolecular glues" in biomedical techniques.
The (strept)avidin-biotin system is a widely-used example, but novel alternatives are sought.
Previous work demonstrated strong binding of squaraine dyes by tetralactam macrocycles with anthracenyl units.

Purpose of the Study:

To develop novel host-guest systems with enhanced binding affinities and selectivities for squaraine dyes.
To explore the potential of pentacyclic 5,7,12,14-tetrahydro-5,7,12,14-tetraoxapentacene (TOP) units in macrocyclic receptors.
To assess the stability and detectability of these new supramolecular complexes.

Main Methods:

Synthesis of tetralactam macrocycles incorporating pentacyclic 5,7,12,14-tetrahydro-5,7,12,14-tetraoxapentacene (TOP) units.
Affinity and selectivity measurements using squaraine dyes as guests.
Spectroscopic analysis (fluorescence and absorbance) to monitor binding events.
Photostability assessments of the TOP-based receptors and their complexes.

Main Results:

Receptors with TOP units exhibited significantly increased binding affinities for squaraine dyes (K_a ≈ 10¹⁰ M^-1) compared to anthracenyl analogs.
Improved selectivity was observed for squaraine dye binding.
Binding interactions were successfully monitored via changes in squaraine fluorescence and absorbance.
The TOP-based receptor demonstrated enhanced photostability, both alone and when complexed with squaraines.

Conclusions:

Replacing anthracenyl units with TOP units in tetralactam macrocycles leads to superior host-guest systems for squaraine dyes.
These TOP-based systems offer high affinities, selectivities, and improved photostability.
The developed system shows significant potential for practical applications in "synthavidin" chemistry and biomedical engineering.