Use of the interaction of a boronic acid with a merocyanine to develop an anionic colorimetric assay

Nicolini, Jaqueline; Testoni, F.; Schuhmacher, Samya Maren; Machado, Vanderlei G.

doi:10.1016/j.tetlet.2007.03.020

Cited by 26 publications

(21 citation statements)

References 41 publications

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“…These observations are consistent with the results obtained from the titrations of 1-PBA with F − (Fig. S3, Supporting information) and to experimental data previously obtained for the titration of 2-PBA in acetonitrile with increasing amounts of F − [35]. Fig.…”

Section: Titrations Of the Dye-pba System With Cn − In Acetonitrilesupporting

confidence: 93%

“…Our research group has developed chromogenic chemosensors for F − and CN − based on solvatochromic compounds having a phenolate moiety in their molecular structure [34][35][36][37][38], such as Reichardt's pyridinium N-phenolate betaine dye, 2,6-diphenyl-4-(2,4,6-triphenylpyridinium-1-yl)phenolate (1), and 1-methyl-4-[(1-oxocyclohexa-2,5-dienylidiene)ethylidene]-1,4-dihydropyridine, known as Brooker's merocyanine (2), which have been commonly used as perichromic probes in the investigation of the polarity of different media [39][40][41][42][43]. Another component of the chemosensor set is comprised of boronic acids which are used in supramolecular devices as efficient recognition units, especially for monosaccharides and anionic species, such as F − and CN − [15,[44][45][46][47][48][49].…”

Section: Introductionmentioning

confidence: 99%

“…Another component of the chemosensor set is comprised of boronic acids which are used in supramolecular devices as efficient recognition units, especially for monosaccharides and anionic species, such as F − and CN − [15,[44][45][46][47][48][49]. Therefore, a displacement strategy involving compound 2 and phenyl boronic acid (PBA) was studied for the development of a chromogenic chemosensor which is highly selective toward F − among other anionic species [35]. Compound 2 in acetonitrile is colored, but it reacts with PBA forming a 2-PBA intermediate which is colorless in solution.…”

Section: Introductionmentioning

confidence: 99%

“…Compound 2 in acetonitrile is colored, but it reacts with PBA forming a 2-PBA intermediate which is colorless in solution. With the addition of F − to the medium the original color of the solution is restored because the anion reacts with the boron center displacing 2 [35]. In other related study, Cha et al developed a chromogenic chemosensor for F − based on a displacement assay using a merocyanine as the signalizing unit and PBA [50].…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Anionic chromogenic chemosensors highly selective for cyanide based on the interaction of phenyl boronic acid and solvatochromic dyes

Zimmermann

Nicolini

Marini

et al. 2015

Sensors and Actuators B: Chemical

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Section: Titrations Of the Dye-pba System With Cn − In Acetonitrilesupporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Anionic chromogenic chemosensors highly selective for cyanide based on the interaction of phenyl boronic acid and solvatochromic dyes

Zimmermann

Nicolini

Marini

et al. 2015

Sensors and Actuators B: Chemical

Self Cite

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“…Sensing ensembles such as these have been developed for a wide range of analytes including chiral diols [68], the anticoagulant oligosaccharide heparin [86], phosphosugars [12], nucleotides [84] and more [41,54,56,83].…”

Section: Displacement Assays As a Measure Of Enzyme Activitymentioning

confidence: 99%

Molecular recognition with boronic acids—applications in chemical biology

2013

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Small molecules have long been used for the selective recognition of a wide range of analytes. The ability of these chemical receptors to recognise and bind to specific targets mimics certain biological processes (such as proteinsubstrate interactions) and has therefore attracted recent interest. Due to the abundance of biological molecules possessing polyhydroxy motifs, boronic acids-which form fivemembered boronate esters with diols-have become increasingly popular in the synthesis of small chemical receptors. Their targets include biological materials and natural products including phosphatidylinositol bisphosphate, saccharides and polysaccharides, nucleic acids, metal ions and the neurotransmitter dopamine. This review will focus on the many ways in which small chemical receptors based on boronic acids have been used as biochemical tools for various purposes, including sensing and detection of analytes, interference in signalling pathways, enzyme inhibition and cell delivery systems. The most recent developments in each area will be highlighted.

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Competition Experiments

You¹,

Anslyn²

2012

Supramolecular Chemistry

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Competition assays, particularly indicator displacement assays (IDAs), are now a popular approach for supramolecular detection and sensing. Contrary to the traditional indicator–spacer–receptor approach, an IDA is based on guest competition between an analyte and an indicator for binding of the receptor (host). As a result, synthesis to incorporate the indicator is avoided in the creation of an IDA, and the selection of indicators can be used to impact the assay. IDAs have been utilized to detect and sense various kinds of analytes, including anions, cations, and neutral molecules. Moreover, both synthetic and biological hosts have been explored in IDAs, thereby expanding the scope of IDAs. Besides utilization in individual analyte sensing, IDAs are amenable to pattern‐recognition‐based differential sensing. Recently, IDAs have been explored to discriminate structurally similar analytes, generating diagnostic fingerprints for complex mixtures. Enantioselective indicator displacement assays (eIDAs) have also been explored and have great potential for application in asymmetric catalyst discovery. IDAs with different detection methods, different kinds of guests, and different kinds of hosts are discussed in this chapter.

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Use of the interaction of a boronic acid with a merocyanine to develop an anionic colorimetric assay

Cited by 26 publications

References 41 publications

Anionic chromogenic chemosensors highly selective for cyanide based on the interaction of phenyl boronic acid and solvatochromic dyes

Anionic chromogenic chemosensors highly selective for cyanide based on the interaction of phenyl boronic acid and solvatochromic dyes

Molecular recognition with boronic acids—applications in chemical biology

Competition Experiments

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