Boronate Affinity Chromatography

Muhammad, Pir; Li, Daojin; Liu, Zhen

doi:10.1002/9780470027318.a9414

Cited by 7 publications

(8 citation statements)

References 80 publications

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“…Boronic acids effectively interact with diols [ 1 – 4 ] that have found application in various fields: in the recognition and sensing of carbohydrates and glycoproteins [ 5 – 11 ], in separation techniques [ 12 ] and in labeling and manipulation of proteins [ 13 – 15 ]. In recent years, boronic acid derivatives were applied in the construction of functional materials, i.e., stimuli-responsive devices and carriers for drug delivery [ 16 – 22 ].…”

Section: Introductionmentioning

confidence: 99%

Closed polymer containers based on phenylboronic esters of resorcinarenes

Sergeeva¹,

Nizameev²,

Kadirov³

et al. 2018

Beilstein J. Nanotechnol.

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Novel polymer nanospheres (p(SRA-B)) were prepared by cross-linking a sulfonated resorcinarene (SRA) with phenylboronic acid. p(SRA-B) shows good stability in water and can be used as a nanocontainer for the pH- and glucose-controlled substrate release. Fluorescent dyes (fluorescein, pyrene and 1,3,6,8-pyrenetetrasulfonic acid tetrasodium salt) were successfully loaded into p(SRA-B). The release of dye is achieved by lowering the pH value to 3 or by adding glucose.

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Section: Introductionmentioning

confidence: 99%

Closed polymer containers based on phenylboronic esters of resorcinarenes

Sergeeva¹,

Nizameev²,

Kadirov³

et al. 2018

Beilstein J. Nanotechnol.

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“…Since then, knowledge obtained from previous studies were further used for subsequent design and preparation of new BAMs . With increased knowledge and understanding, we proposed a suite of strategies for selectivity adjustment . As illustrated in Figure , besides boronate affinity interaction, multiple secondary interactions, primarily including hydrophobic interaction, ionic interaction, and hydrogen bonding, can occur on BAMs, while Lewis base effect (Lewis acid–base coordination) favors complexation under less basic conditions.…”

Section: Novel Boronate Affinity Materialsmentioning

confidence: 99%

“…Green arrows, favorable interaction; cyan arrows, unfavorable interactions; red up arrow, the interaction can be enhanced by the means specified; blue down arrows, the interactions can be suppressed by the means specified. Adapted with the permission from ref . Copyright 2015 Wiley.…”

Section: Novel Boronate Affinity Materialsmentioning

confidence: 99%

Synthesis and Applications of Boronate Affinity Materials: From Class Selectivity to Biomimetic Specificity

2017

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Due to the complexity of biological systems and samples, specific capture and targeting of certain biomolecules is critical in much biological research and many applications. cis-Diol-containing biomolecules, a large family of important compounds including glycoproteins, saccharides, nucleosides, nucleotides, and so on, play essential roles in biological systems. As boronic acids can reversibly bind with cis-diols, boronate affinity materials (BAMs) have gained increasing attention in recent years. However, real-world applications of BAMs are often severely hampered by three bottleneck issues, including nonbiocompatible binding pH, weak affinity, and difficulty in selectivity manipulation. Therefore, solutions to these issues and knowledge about the factors that influence the binding properties are of significant importance. These issues have been well solved by our group in past years. Our solutions started from the synthesis and screening of boronic acid ligands with chemical moieties favorable for binding at neutral and acidic pH. To avoid tedious synthesis routes, we proposed a straightforward strategy called teamed boronate affinity, which permitted facile preparation of BAMs with strong binding at neutral pH. To enhance the affinity, we confirmed that multivalent binding could significantly enhance the affinity toward glycoproteins. More interestingly, we observed that molecular interactions could be significantly enhanced by confinement within nanoscale spaces. To improve the selectivity, we investigated interactions that govern the selectivity and their interplays. We then proposed a set of strategies for selectivity manipulation, which proved to be useful guidelines for not only the design of new BAMs but also the selection of binding conditions. Applications in metabolomic analysis, glycoproteomic analysis, and aptamer selection well demonstrated the great potential of the prepared BAMs. Molecular imprinting is an important methodology for creating affinity materials with antibody-like binding properties. Boronate affinity-based covalent imprinting is a pioneering approach in molecular imprinting, but only a few cases of successful imprinting of glycoproteins by this method were reported. With sound understanding of boronate affinity, we developed two facile and generally applicable boronate affinity-based molecular imprinting approaches. The resulting boronate affinity molecularly imprinted polymers (MIPs) exhibited dramatically improved binding properties, including biocompatible binding pH range, enhanced affinity, improved specificity, and superb tolerance to interference. In terms of nanoconfinement effect, we explained why the binding pH range was widened and why the affinity was enhanced. The excellent binding properties made boronate affinity MIPs appealing alternatives to antibodies in promising applications such as disease diagnosis, cancer-cell targeting, and single-cell analysis. In this Account, we survey the key aspects of BAMs, the efforts we made to solve these issues, and the connection...

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“…In brief, boronic acids could form ve or six-membered cyclic esters with cis-diols under high pH conditions (usually alkaline conditions) and the cyclic esters will dissociate when the environmental medium is changed to acidic conditions. 39 This pH-controlled capture and release property made boronate affinity materials (BAMs) promising sorbents for the enrichment of cis-diols. 40,41 However, real-world applications of BAMs were oen severely hampered by nonbiocompatible binding pH and weak affinity.…”

Section: Introductionmentioning

confidence: 99%