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DC Field | Value | Language |
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dc.contributor.author | Chowdhury, A. | - |
dc.contributor.author | Chatterjee, S. | - |
dc.contributor.author | Kushwaha, A. | - |
dc.contributor.author | Kumar, T. J. D | - |
dc.contributor.author | Bandyopadhyay, A. | - |
dc.date.accessioned | 2024-07-07T08:04:34Z | - |
dc.date.available | 2024-07-07T08:04:34Z | - |
dc.date.issued | 2024-07-07 | - |
dc.identifier.uri | http://dspace.iitrpr.ac.in:8080/xmlui/handle/123456789/4671 | - |
dc.description.abstract | Finding an ideal bioorthogonal reaction that responds to a wide range of biological queries and applications is of great interest in biomedical applications. Rapid diazaborine (DAB) formation in water by the reactions of ortho-carbonyl phenylboronic acid with α-nucleophiles is an attractive conjugation module. Nevertheless, these conjugation reactions demand to satisfy stringent criteria for bioorthogonal applications. Here we show that widely used sulfonyl hydrazide (SHz) offers a stable DAB conjugate by combining with ortho-carbonyl phenylboronic acid at physiological pH, competent for an optimal biorthogonal reaction. Remarkably, the reaction conversion is quantitative and rapid (k2>103 M−1 s−1) at low micromolar concentrations, and it preserves comparable efficacy in a complex biological milieu. DFT calculations support that SHz facilitates DAB formation via the most stable hydrazone intermediate and the lowest energy transition state compared to other biocompatible α-nucleophiles. This conjugation is extremely efficient on living cell surfaces, enabling compelling pretargeted imaging and peptide delivery. We anticipate this work will permit addressing a wide range of cell biology queries and drug discovery platforms exploiting commercially available sulfonyl hydrazide fluorophores and derivatives. | en_US |
dc.language.iso | en_US | en_US |
dc.title | Sulfonyl Diazaborine ‘Click’ Chemistry Enables Rapid and Efficient Bioorthogonal Labeling | en_US |
dc.type | Article | en_US |
Appears in Collections: | Year-2023 |
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full text.pdf | 1.54 MB | Adobe PDF | View/Open Request a copy |
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