Recent applications of CBT-Cys click reaction in biological systems

Zhu, Yuechao; Zhang, Xian; Qin, You; Jiang, Zhengyu

doi:10.1016/j.bmc.2022.116881

Cited by 13 publications

(7 citation statements)

References 75 publications

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“…Several electrophilic groups were developed to selectively target proteins with N-terminal Cys, − e.g., thioesters, O -salicylaldehyde esters, activated aldehydes, activated nitriles, 2-((alkylthio)(aryl)methylene)malononitriles, N -hydroxysuccinimide-activated acrylamides, 2-benzylacrylaldehydes, 2-formylphenylboronic acids, − and monosubstituted cyclopropenones . Here, we focused on activated heteroaromatic nitriles, which were found to have a wide range of applicability in recent years. ,− Inspired by the final step in the biosynthesis of d -luciferin, Rao and co-workers utilized a click reaction between 2-cyanobenzothiazole and N-terminal Cys for protein labeling . In the first step, addition of the thiol to the nitrile leads to reversible formation of the thioimidate intermediate (Figure A), which is followed by an intramolecular condensation reaction with amine to form the 2-aminothiazolidine intermediate.…”

Section: Introductionmentioning

confidence: 99%

“…25 A wide range of applications have been demonstrated for the reaction between heterocyclic nitriles and 1,2-aminothiols as summarized in recent reviews. 21,23,24 To exemplify, sitespecific labeling of proteins with N-terminal Cys has been exploited for imaging, drug delivery, and protein immobilization (Figure 1B). In addition to protein labeling, the same reaction is also used for the controllable in situ assembly of bioactive compounds and nanostructures (Figure 1C).…”

Section: ■ Introductionmentioning

confidence: 99%

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Tunable Heteroaromatic Nitriles for Selective Bioorthogonal Click Reaction with Cysteine

et al. 2023

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The binucleophilic properties of 1,2-aminothiol and its rare occurrence in nature make it a useful reporter for tracking molecules in living systems. The 1,2-aminothiol moiety is present in cysteine, which is a substrate for a biocompatible click reaction with heteroaromatic nitriles. Despite the wide range of applications for this reaction, the scope of nitrile substrates has been explored only to a limited extent. In this study, we expand the chemical space of heteroaromatic nitriles for bioconjugation under physiologically relevant conditions. We systematically assembled a library of 116 2-cyanobenzimidazoles, 1-methyl-2cyanobenzimidazoles, 2-cyanobenzothiazoles, and 2-cyanobenzoxazoles containing electron-donating and electron-withdrawing substituents at all positions of the benzene ring. The compounds were evaluated for their stability, reactivity, and selectivity toward the N-terminal cysteine of model oligopeptides. In comparison to the benchmark 6-hydroxy-2-cyanobenzothiazole or 6-amino-2cyanobenzothiazole, we provide highly selective and moderately reactive nitriles as well as highly reactive yet less selective analogs with a variety of enabling attachment chemistries to aid future applications in bioconjugation, chemical biology, and nanomaterial science.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Tunable Heteroaromatic Nitriles for Selective Bioorthogonal Click Reaction with Cysteine

et al. 2023

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“…Moreover, the reaction processes have characteristics such as simple operation, mild reaction conditions (not sensitive to oxygen and water), high selectivity and so high reaction yield along with nondifficult purification/product isolation technique. Within this scope, among the mentioned multicomponent reactions that offer many opportunities for a great number of post-condensation cyclizations, cycloaddition between azides and alkynes (Huisgen reaction) has gained much more and ever-increasing attention in consequence of yielding potentially biological active 1,2,3-triazole compounds [10][11][12] .…”

Section: Introductionmentioning

confidence: 99%

Click chemistry: A fascinating, Nobel-winning method for the improvement of biological activity

Halay

Açıkbaş

2023

ACE

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Click chemistry is totally an approach consisting of efficient and reliable reactions that bind two molecular building blocks and require no complex purification techniques. The aspire of achieving molecules with the desired characteristics and behaviour is the key to the click chemistry concept. In this concept, in order to obtain 1,2,3-triazole products as diversely functionalized molecules, copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction has been widely used for years in the field of materials science, organic synthesis and the biochemistry. This review focusses on the importance of click chemistry for obtaining biologically active triazole molecules and therefore the applications of such 1,2,3-triazole derivatives in medicinal chemistry field are highlighted.

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“…In brief, these CBT-Cys probes/prodrugs were "co-incubated" with their labeling-free precursors (25 or 50 µM) for administration to conquer the interference of intracellular Cys (20-100 µM) and warrant their self-assemblies inside cells. 16,27,28,[29][30][31][32][33] There were some excellent reviews on the applications of CBT-Cys click reaction for in vivo bioimaging recently published, [34][35][36][37][38] but they did not include or emphatically review recent breakthroughs in this field, particularly in recent 5 years. Hence, we propose this mini-review, aiming to highlight recent remarkable and inspiring achievements of CBT-Cys click reaction for in vivo optical bioimagings including fluorescence imaging (FLI), bioluminescence imaging (BLI), photoacoustic imaging (PAI), and multimodal imaging (Figure 1 and Table 1).…”

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confidence: 99%

CBT‐Cys click reaction for optical bioimaging in vivo

Tang

Bai

et al. 2023

VIEW

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Derived from the D‐luciferin regeneration pathway in firefly body, the click condensation reaction between 2‐cyanobenzothiazole (CBT) and D‐cysteine (Cys) (CBT‐Cys click reaction) possesses unique advantages, including superior biocompatibility, high second order reaction rate, and metal‐free mild conditions, emerging as a powerful bioorthogonal tool for a variety of chemical biological applications. Moreover, owing to its programmable controllability (e.g., pH, reduction, or enzyme), CBT‐Cys click reaction is exploited to fabricate stimuli‐activatable imaging probes with self‐assembling behaviors in physiological context. At stimuli‐rich pathological lesions of interest, these probes undergo CBT‐Cys click reaction to form cyclic dimers/oligomers or linear polymers, and further self‐assemble into nanostructures. The in situ formed nanostructures promote the selective accumulation and retention of imaging agent cargos at pathological lesions, thus enabling precise and enhanced in vivo imaging of diseases (especially tumors). To address the significance and recent breakthroughs of smart CBT‐Cys probes for enhanced optical imaging of tumors/other diseases, we herein propose this mini‐review, in which advances (particularly in recent 5 years) and potential challenges (or chances) in this field are emphasized.

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Recent applications of CBT-Cys click reaction in biological systems

Cited by 13 publications

References 75 publications

Tunable Heteroaromatic Nitriles for Selective Bioorthogonal Click Reaction with Cysteine

Tunable Heteroaromatic Nitriles for Selective Bioorthogonal Click Reaction with Cysteine

Click chemistry: A fascinating, Nobel-winning method for the improvement of biological activity

CBT‐Cys click reaction for optical bioimaging in vivo

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