A simple ionic triphenylene receptor for catecholamines, serotonin and d-glucosamine in buffered water

Givelet, Cécile; Bibal, Brigitte

doi:10.1039/c1ob06099f

Cited by 13 publications

(4 citation statements)

References 31 publications

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“…[ 56,57 ] The selectivity of SBs is expectedly even lower (selectivity ratio <3, Table S7, Supporting Information). [ 32–34 ] Likewise, ZARs become more selective for serotonin over dopamine in the presence of salts (selectivity ratio of 17 in water versus 40 in phosphate buffer, Figure 5f–h and Table S4 and S7, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…[56,57] The selectivity of SBs is expectedly even lower (selectivity ratio <3, Table S7, Supporting Information). [32][33][34] Likewise, ZARs become more selective for serotonin over dopamine in the presence of salts (selectivity ratio of 17 in water versus 40 in phosphate buffer, Figure 5f-h S3 and S6, Supporting Information), known SBs (orange; Tables S6 and S7, Supporting Information), and ZAR1 (blue; Table S5, Supporting Information) in water and buffered aqueous media. g,h) Binding titrationexperiments monitored by fluorescence spectroscopy at λ em = 424 nm for FAR1 with g) serotonin and h) dopamine as function of the salinity ofthe aqueous medium.…”

Section: Zar-based Neurotransmitter Distinctionmentioning

confidence: 99%

“…However, to our knowledge, they do not fulfill the affinity and selectivity requirements for diagnostic applications in biofluids. [26][27][28] We assess that all contemporary SBs for serotonin and dopamine (Figure 1, Figure S3 and Table S7, Supporting Information) that were rationally designed performed very poorly, [1,[29][30][31][32][33][34] because i) their affinity for the target molecules is too low, particularly in aqueous media and in the presence of salts; ii) their binding selectivity is insufficient, for example, they cannot distinguish neurotransmitters from amino acids; and/or iii) they lack in a signal transduction mode and therefore are no receptors. Clearly, the currently pursued design principles for SBs need to be complemented with novel strategies.…”

Section: Introductionmentioning

confidence: 99%

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Fluorescent Nanozeolite Receptors for the Highly Selective and Sensitive Detection of Neurotransmitters in Water and Biofluids

et al. 2021

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The design and preparation of synthetic binders (SBs) applicable for small biomolecule sensing in aqueous media remains very challenging. SBs designed by the lock‐and‐key principle can be selective for their target analyte but usually show an insufficient binding strength in water. In contrast, SBs based on symmetric macrocycles with a hydrophobic cavity can display high binding affinities but generally suffer from indiscriminate binding of many analytes. Herein, a completely new and modular receptor design strategy based on microporous hybrid materials is presented yielding zeolite‐based artificial receptors (ZARs) which reversibly bind the neurotransmitters serotonin and dopamine with unprecedented affinity and selectivity even in saline biofluids. ZARs are thought to uniquely exploit both the non‐classical hydrophobic effect and direct non‐covalent recognition motifs, which is supported by in‐depth photophysical, and calorimetric experiments combined with full atomistic modeling. ZARs are thermally and chemically robust and can be readily prepared at gram scales. Their applicability for the label‐free monitoring of important enzymatic reactions, for (two‐photon) fluorescence imaging, and for high‐throughput diagnostics in biofluids is demonstrated. This study showcases that artificial receptor based on microporous hybrid materials can overcome standing limitations of synthetic chemosensors, paving the way towards personalized diagnostics and metabolomics.

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Section: Resultsmentioning

confidence: 99%

Section: Zar-based Neurotransmitter Distinctionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Fluorescent Nanozeolite Receptors for the Highly Selective and Sensitive Detection of Neurotransmitters in Water and Biofluids

et al. 2021

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“…A common strategy is to suitably functionalize the backbone of artificial receptors whose binding properties toward selected substrates have been already successfully studied in lipophilic media, to allow their solubilization in water …”

Section: Introductionmentioning

confidence: 99%

A Route to Oligosaccharide-Appended Salicylaldehydes: Useful Building Blocks for the Synthesis of Metal–Salophen Complexes

Bedini

Forte

Castro³

et al. 2013

J. Org. Chem.

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A simple and general synthetic protocol to obtain oligosaccharide-appended salicylaldehydes, key intermediates for the synthesis of water-soluble metal-salophen complexes, is here reported. Six new aldehydes have been prepared and fully characterized as well as the corresponding zinc- and uranyl-salophen complexes. These new derivatives show very good solubility in water. Preliminary studies on the association of compound 19-U, that is, the uranyl maltotetraose derivative, with hydrogen phosphate and fluoride provide very encouraging results and open up the possibility of using such compounds for the efficient recognition of anions in pure water.

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Affinity Enhancement by Dendritic Side Chains in Synthetic Carbohydrate Receptors

et al. 2015

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Dendritic side chains have been used to modify the binding environment in anthracene-based synthetic carbohydrate receptors. Control of length, charge, and branching enabled the positioning of side-chain carboxylate groups in such a way that they assisted in binding substrates rather than blocking the cavity. Conformational degeneracy in the dendrimers resulted in effective preorganization despite the flexibility of the system. Strong binding was observed to glucosammonium ions in water, with K a values up to 7000 m À1 . Affinities for uncharged substrates (glucose and N-acetylglucosamine) were also enhanced, despite competition from solvent and the absence of electrostatic interactions.

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A simple ionic triphenylene receptor for catecholamines, serotonin and d-glucosamine in buffered water

Abstract: The combination of hydrophobic effects and ionic pairing within a triphenylene-based receptor were exploited for the binding of biological phenylethylamines, serotonin and D-glucosamine in phosphate buffered water.

Cited by 13 publications

References 31 publications

Fluorescent Nanozeolite Receptors for the Highly Selective and Sensitive Detection of Neurotransmitters in Water and Biofluids

Fluorescent Nanozeolite Receptors for the Highly Selective and Sensitive Detection of Neurotransmitters in Water and Biofluids

A Route to Oligosaccharide-Appended Salicylaldehydes: Useful Building Blocks for the Synthesis of Metal–Salophen Complexes

Affinity Enhancement by Dendritic Side Chains in Synthetic Carbohydrate Receptors

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