A supramolecular cucurbit[8]uril-based rotaxane chemosensor for the optical tryptophan detection in human serum and urine

Abstract

Sensing small biomolecules in biofluids remains challenging for many optical chemosensors based on supramolecular host-guest interactions due to adverse interplays with salts, proteins, and other biofluid components. Instead of following the established strategy of developing alternative synthetic binders with improved affinities and selectivity, we report a molecular engineering approach that addresses this biofluid challenge. Here we introduce a cucurbit[8]uril-based rotaxane chemosensor feasible for sensing the health-relevant biomarker tryptophan at physiologically relevant concentrations, even in protein- and lipid-containing human blood serum and urine. Moreover, this chemosensor enables emission-based high-throughput screening in a microwell plate format and can be used for label-free enzymatic reaction monitoring and chirality sensing. Printed sensor chips with surface-immobilized rotaxane-microarrays are used for fluorescence microscopy imaging of tryptophan. Our system overcomes the limitations of current supramolecular host-guest chemosensors and will foster future applications of supramolecular sensors for molecular diagnostics.

Polyrotaxane‐Based Functional Materials Enabled by Molecular Mobility and Conformational Transition†

“…[ 185‐187 ] Polyrotaxanes with slide‐ring structure are receiving more and more attention in biomedical fields including drug release, theranostics, bioimaging, chemical sensing, and biointerfaces. [ 188‐191 ]…”

Surface Engineering of MoS2 Quantum Dots via Cyclodextrin-Based Host–Guest Chemistry as Versatile Platforms for Enhanced Cell Imaging Application

“…Microplate reader-based fluorescence assay can provide a high throughput, convenient, and fast analysis platform, which has a wide range of applications in biomedicine, chemical detection, and other fields. 60,61 Encouraged by the above results, we further investigated the potential utility of FA-MoS 2 QDs for cell recognition in a microplate. Upon seeding cells in the microplate, FA-MoS 2 QDs and β-CD-MoS 2 QDs were added and incubated for 2 h. After removing free QDs, fluorescence signals of cells were recorded by the microplate reader (Figure 7a).…”

Methodologies for Spontaneous Preparation of Chemosensors and Their Arrays Using Off‐the‐Shelf Reagents

“…Each role of the off-the-shelf building block in the displacement assays contributed to obtaining fingerprint-like response profiles for pattern recognition in real samples. Recently, the potential of chemosensors in practical sensing applications has been reported; [14,[120][121][122][123][124][125][126][127][128] however, their favorable sensing performance still relies on complicated molecular designs that require multiple steps of organic synthesis. In other words, the detectable analyte structures are limited by the structure of building blocks of chemosensors.…”