Fluorogenic diazaborine formation of semicarbazide with designed coumarin derivatives

Cambray, Samantha; Bandyopadhyay, Anupam; Gao, Jianmin

doi:10.1039/c7cc07389e

Cited by 32 publications

(28 citation statements)

References 24 publications

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“…180 This first attempt at a turn-on fluorescent DAB paved the way for future research in this area and, one year later, Gao and co-workers reported a new fluorogenic DAB. 183 By synthesizing a modified coumarin bearing a 2-ABBA side-chain, the fluorescence was quenched, and the authors envisioned that, upon reaction with semicarbazide, the molecule would regain its fluorescence. The resulting diazaborine showed a 7-fold increase in fluorescence intensity when compared to the starting reactants.…”

Section: Boronated Oximes and Diazaborinesmentioning

confidence: 99%

Boronic acids as building blocks for the construction of therapeutically useful bioconjugates

et al. 2019

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Section: Boronated Oximes and Diazaborinesmentioning

confidence: 99%

Boronic acids as building blocks for the construction of therapeutically useful bioconjugates

et al. 2019

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“…More recently, we reported fluorogenic versions of the diazaborine conjugation chemistry, which reduce the background fluorescence to allow even better visualization of bacterial pathogens. 44…”

Section: Bioorthogonal Conjugation With Designer Nucleophilesmentioning

confidence: 99%

Versatile Bioconjugation Chemistries of ortho-Boronyl Aryl Ketones and Aldehydes

Cambray

Gao

2018

Acc. Chem. Res.

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Biocompatible and bioorthogonal conjugation reactions have proven to be powerful tools in biological research and medicine. While the advent of bioorthogonal conjugation chemistries greatly expands our capacity to interrogate specific biomolecules in situ, biocompatible reactions that target endogenous reactive groups have given rise to a number of covalent drugs as well as a battery of powerful research tools. Despite the impressive progress, limitations do exist with the current conjugation chemistries. For example, most known bioorthogonal conjugations suffer from slow reaction rates and imperfect bioorthogonality. On the other hand, covalent drugs often display high toxicity due to off-target labeling and immunogenicity. These limitations demand continued pursuit of conjugation chemistries with optimal characteristics for biological applications. A spate of papers appearing in recent literature report the conjugation chemistries of 2-formyl and 2-acetyl phenylboronic acids (abbreviated as 2-FPBA and 2-APBA, respectively). These simple reactants are found to undergo fast conjugation with various nucleophiles under physiological conditions, showing great promise for biological applications. The versatile reactivity of 2-FPBA and 2-APBA manifests in dynamic conjugation with endogenous nucleophiles as well as conjugation with designer nucleophiles in a bioorthogonal manner. 2-FPBA/APBA conjugates with amines in biomolecules, such as lysine side chains and aminophospholipids, in a highly dynamic manner to give iminoboronates. In contrast to typical imines, iminoboronates enjoy much improved thermodynamic stability, yet are kinetically labile for hydrolysis due to imine activation by the boronic acid. Dynamic conjugations as such present a novel binding mechanism analogous to hydrogen bonding and electrostatic interactions. Implementation of this covalent binding mechanism has yielded reversible covalent probes of prevalent bacterial pathogens. It has also resulted in reversible covalent inhibitors of a therapeutically important protein Mcl-1. Such covalent probes/inhibitors with 2-FPBA/APBA warheads avoid permanent modification of their biological target, potentially able to mitigate off-target labeling and immunogenicity of covalent drugs. The dynamic conjugation of 2-FPBA/APBA has been recently extended to N-terminal cysteines, which can be selectively targeted via formation of a thiazolidino boronate (TzB) complex. The dynamic TzB formation expands the toolbox for site-specific protein labeling and the development of covalent drugs. On the front of bioorthogonal conjugation, 2-FPBA/APBA has been found to conjugate with α-nucleophiles under physiologic conditions with rate constant ( k) over 1000 M s, which overcomes the slow kinetics problems and rekindles the interest of using the conjugation of α-nucleophiles for biological studies. With fast kinetics being a shared feature, this family of conjugation chemistries gives remarkably diverse product structures depending on the choice of nucleophile. Importantly, ...

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“… 45 Remarkably, 2-APBA and semicarbazide were demonstrated to be a “sweet partner” in developing ideal biorthogonal reactions formation as reactants and product do not exhibit toxicity, and the reaction can be used for selective bacterial detection ( Fig. 7f ) via peptidoglycan modification of fluorogenic probe 52 or fluorophore-labeled conjugates. 45 …”

Section: Iminoboronate Chemistrymentioning

confidence: 99%

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

2021

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Fluorogenic diazaborine formation of semicarbazide with designed coumarin derivatives

Cited by 32 publications

References 24 publications

Boronic acids as building blocks for the construction of therapeutically useful bioconjugates

Boronic acids as building blocks for the construction of therapeutically useful bioconjugates

Versatile Bioconjugation Chemistries of ortho-Boronyl Aryl Ketones and Aldehydes

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

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