Boronic acid based dynamic click chemistry: recent advances and emergent applications

Chatterjee, Saurav; Anslyn, Eric V.; Bandyopadhyay, Anupam

doi:10.1039/d0sc05009a

Cited by 73 publications

(67 citation statements)

References 78 publications

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“…It should be noted that the question of a meaningful definition of “click chemistry” in connection with polymer synthesis and post‐polymerization modifications deserves caution 134 . In polymer chemistry, the list of available “click” reactions is far longer than that in Table 1 and it comprises Diels‐Alder, Alder‐ene, thio‐bromo, 1,2,4‐triazoline‐3,5‐dione, amino‐yne, and boronic acid‐based chemistry 135–137 . Our feeling, then, is that the potential of “click” reactions in the field of MSR polymers, granted by the orthogonality of these reactions, is not fully deployed to‐date.…”

Section: Click and Other Reactions For Post‐polymerization Assembly And Modificationsmentioning

confidence: 99%

Playing construction with the monomer toy box for the synthesis of multi‐stimuli responsive copolymers by reversible deactivation radical polymerization protocols

D’Acunzo

Masci

2021

Journal of Polymer Science

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In this review article, we survey the 2016–June 2021 scientific literature on the synthesis of multi‐stimuli responsive (MSR) polymers, the main focus being on reversible deactivation radical polymerization techniques (RDRPs, also known as controlled radical polymerizations). In fact, along more than 40 years of extensive research, RDRPs have boosted the synthesis of stimuli‐responsive polymers. RDRPs are now robust, versatile, relatively user‐friendly and even interconvertible, thus allowing control over composition, sequence, and topology of polymers. Such control can afford materials with well‐defined responses to physical, chemical, and biological external stimuli. Furthermore, “click” reactions are used to combine macromolecular precursors or to introduce specific functional groups in the target structure. As a result, MSR polymers are obtained from diverse combinations of commercial or specially synthesized building blocks arranged at will into desired sequences and architectures. Thanks to this versatility, self‐assembling polymeric structures are designed either to respond to triggers and perform specific applicative tasks, or to investigate the influence of structural variables on the responsivity of polymers. The “green” trend emerging in the field of responsive polymers and RDRPs is also briefly discussed.

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Section: Click and Other Reactions For Post‐polymerization Assembly And Modificationsmentioning

confidence: 99%

Playing construction with the monomer toy box for the synthesis of multi‐stimuli responsive copolymers by reversible deactivation radical polymerization protocols

D’Acunzo

Masci

2021

Journal of Polymer Science

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“…Boronic acids (BAs) have lately gained much attention in the site‐specific formation of bioconjugates [24,25] . Reversible covalent complex formation between BA derivatives and 1,2‐ or 1,3‐ cis diol motifs, such as those typically present in biological polyols, including saccharides and glycocalyx, has emerged as an attractive bioorthogonal reaction for the chemical modification of glycoproteins [26] .…”

Section: Introductionmentioning

confidence: 99%

Investigating a Boronate‐Affinity‐Guided Acylation Reaction for Labelling Native Antibodies

Lin

Adak

Huang

et al. 2022

Chemistry A European J

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The excellent molecular recognition capabilities of monoclonal antibodies (mAbs) have opened up exciting opportunities for biotherapeutic discovery. Taking advantage of the full potential of this tool necessitates affinity ligands capable of conjugating directly with small molecules to a defined degree of biorthogonality, especially when modifying natural Abs. Herein, a bioorthogonal boronate‐affinity‐based Ab ligand featuring a 4‐(dimethylamino)pyridine and an S‐aryl thioester to label full‐length Abs is reported. The photoactivatable linker in the acyl donor facilitated purification of azide‐labelled Ab (N3‐Ab) was quantitatively cleaved upon brief exposure to UV light while retaining the original Ab activity. Click reactions enabled the precise addition of biotin, a fluorophore, and a pharmacological agent to the purified N3‐Abs. The resulting immunoconjugate showed selectivity against targeted cells. Bioorthogonal traceless design and reagentless purification allow this strategy to be a powerful tool to engineer native antibodies amenable to therapeutic intervention.

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“…[26][27][28][29][30] The rate of formation of cyclic boronate ester is enhanced by the condensation between ortho carbonyl (aldehyde or ketone) and amine. 31 Nitrogen atom of imine bond donates its lone pair of electrons to the boron center through a dative bond facilitating the formation of tetrahedral boronate ion. 32 Exploiting this behaviour of boronic acid, hydrogel based optical diffuser has been reported.…”

Section: Introductionmentioning

confidence: 99%

Dynamic Multicomponent Reactions Directed Self-assembled G-quadruplex Inherent Antibacterial Hydrogel

Rit

Ghosh

Patidar

et al. 2022

Preprint

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Now-a-days inherent antibacterial hydrogels have gained significant attention due to their utilization against infectious bacteria. Herein, we focus on the development of injectable, self-healable, dynamic, G-quadruplex hydrogel with inherent antibacterial activity. The dynamic self-assembled hydrogel is constructed upon multicomponent reactions (MCR) among guanosine, 2-formylphenylboronic acid and amino acid/peptides in presence of potassium ions. The role of amino acid/peptides toward the formation of G-quadruplex hydrogel is studied in details. G-quadruplex structure is formed via the π-π stacking of G-quartets. The formation of G-quadruplex is investigated by thioflavin T binding assay, CD spectroscopy and PXRD. The formation of the dynamic imino-boronate bond in the hydrogels is well characterised by temperature dependent 11B NMR (VT-NMR) and FT-IR spectroscopy. Furthermore HR-TEM images and rheological experiments reveal the fibrillar networks and the viscoelastic property of the hydrogels. The presence of the dynamic imino-boronate ester bonds makes the hydrogel injectable and self-healable in nature. These dynamic G-quadruplex hydrogels show potential antibacterial activity against a series of Gram positive and Gram negative bacteria. Such injectable and self-healable hydrogels could be used in various applications in the field of biomedical science.

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Boronic acid based dynamic click chemistry: recent advances and emergent applications

Abstract: Fundamental progress, current developments, and rapidly growing applications of iminoboronate and salicylhydroxamic–boronate conjugate esters are deliberated.

Cited by 73 publications

References 78 publications

Playing construction with the monomer toy box for the synthesis of multi‐stimuli responsive copolymers by reversible deactivation radical polymerization protocols

Playing construction with the monomer toy box for the synthesis of multi‐stimuli responsive copolymers by reversible deactivation radical polymerization protocols

Investigating a Boronate‐Affinity‐Guided Acylation Reaction for Labelling Native Antibodies

Dynamic Multicomponent Reactions Directed Self-assembled G-quadruplex Inherent Antibacterial Hydrogel

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