Journal of the American Chemical Society, Год журнала: 2024, Номер unknown
Опубликована: Дек. 11, 2024
We develop a latent biocompatible cleavage reaction involving the hitherto unexplored interaction between hydroxylamines and cyclopropenones. Our study addresses regioselectivity challenges commonly observed in asymmetric cyclopropenone transformations, substantiated by variations substrate, Density Functional Theory calculations,
Язык: Английский
Journal of the American Chemical Society, Год журнала: 2022, Номер 144(23), С. 10396 - 10406
Опубликована: Июнь 5, 2022
Protein conjugates are valuable tools for studying biological processes or producing therapeutics, such as antibody–drug conjugates. Despite the development of several protein conjugation strategies in recent years, ability to modify one specific amino acid residue on a presence other reactive side chains remains challenge. We show that monosubstituted cyclopropenone (CPO) reagents react selectively with 1,2-aminothiol groups N-terminal cysteine residues give stable 1,4-thiazepan-5-one linkage under mild, biocompatible conditions. The CPO-based reagents, all accessible from common activated ester CPO-pentafluorophenol (CPO-PFP), allow selective modification cysteine-containing peptides and proteins even internal, solvent-exposed residues. This approach enabled preparation dual conjugate 2×cys-GFP, containing both internal residues, by first modifying reagent followed traditional cysteine-modifying reagent. copper-free click reaction between two proteins, dimer de novo mimic IL2 binds β-IL2 receptor low nanomolar affinity. Importantly, compatible reducing agent dithiothreitol (DTT), useful property working prone dimerization. Finally, quantum mechanical calculations uncover origin selectivity distinguish specifically target facilitates construction elaborate multilabeled bioconjugates minimal engineering.
Язык: Английский
Процитировано
43
Chemical & Biomedical Imaging, Год журнала: 2023, Номер 1(7), С. 590 - 619
Опубликована: Май 30, 2023
Among the recent development of click chemistry and bioorthogonal chemistry, fluorogenic reactions occupy a unique place in that fluorescence is generated from nonfluorescent reactants, thereby rendering them highly useful convenient no-wash live-cell imaging. This topic was extensively reviewed 2010 by Wang et al. ( Chem. Soc. Rev. 2010, 39, 1233−1239) 2014 Lin Curr. Opin. Biol. 2014, 21, 89−95). review presents comprehensive up-to-date overview on past decade. The are classified into four major categories basis mechanisms generation. Representative examples each type discussed briefly terms structure, mechanism, advantages. We describe latest applications chemical biology. In end, future opportunities challenges this field tentatively proposed.
Язык: Английский
Процитировано
36
Chem, Год журнала: 2023, Номер 9(8), С. 2095 - 2109
Опубликована: Июнь 5, 2023
Язык: Английский
Процитировано
28
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(10)
Опубликована: Янв. 20, 2024
Developing fluorogenic probes for simultaneous live cell labeling of multiple targets is crucial understanding complex cellular events. The emerging [4+1] cycloaddition between tetrazine and isonitriles holds promise as a bioorthogonal tool, yet existing lack reactivity fluorogenicity. Here, we present the development series tetrazine-functionalized probes. By incorporating pyrazole adducts into fluorophore scaffolds, post-reacted displayed remarkable fluorescence turn-on ratios, up to 3184-fold. Moreover, these modifications are generalizable various fluorophores, enabling broad emission range from 473 659 nm. Quantum chemical calculations further elucidate mechanisms. These enable in cells, without need washing step. Consequently, our findings pave way advanced multiplex imaging detection techniques studies.
Язык: Английский
Процитировано
11
Advanced Materials, Год журнала: 2024, Номер unknown
Опубликована: Ноя. 5, 2024
Abstract Chemical reactions underpin biological processes, and imbalances in critical biochemical pathways within organisms can lead to the onset of severe diseases. Within this context, emerging field “Nanocatalytic Medicine” leverages nanomaterials as catalysts modulate fundamental chemical specific microenvironments This approach is designed facilitate targeted synthesis localized accumulation therapeutic agents, thus enhancing treatment efficacy precision while simultaneously reducing systemic side effects. The effectiveness these nanocatalytic strategies critically hinges on a profound understanding kinetics intricate interplay particular pathological ensure effective catalytic actions. review methodically explores situ their associated biomaterials, emphasizing regulatory that control responses. Furthermore, discussion encapsulates crucial elements‐reactants, catalysts, reaction conditions/environments‐necessary for optimizing thermodynamics reactions, rigorously addressing both biophysical dimensions disease enhance outcomes. It seeks clarify mechanisms underpinning biomaterials evaluate potential revolutionize across various conditions.
Язык: Английский
Процитировано
4
Advanced Synthesis & Catalysis, Год журнала: 2025, Номер unknown
Опубликована: Янв. 23, 2025
Abstract Imidazolium‐dithiocarboxylate zwitterions (NHC ⋅ CS 2 ), a novel organocatalyst that derived from N‐heterocyclic carbene (NHC), was used to activate cyclopropenones. Under the catalysis of 10 mol% NHC 2, range phenols, alcohols, primary and secondary amines react with cyclopropenones produce trisubstituted α , β ‐unsaturated esters amides in 46–95% yield. More than 68 products, including 7 natural product derivatives have been synthesized through this method. Mechanism study showed act as Lewis base C=C double bond trigger ring‐opening reaction. HRMS analysis indicated formation key adduct cyclopropenone. importantly, demonstrated completely different catalytic activity catalysts, latter one cannot catalyse these reactions.
Язык: Английский
Процитировано
0
Chemical Society Reviews, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
In this review, recent progress in tetrazine-based fluorogenic probes for bioorthogonal chemistry is comprehensively analyzed, with a focus on advancements probe design and their imaging applications molecular processes live cells.
Язык: Английский
Процитировано
0
Biomaterials Science, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
Nanotechnology combined with bioorthogonal approaches provides unique routes to improving nuclear medicine imaging and therapy, opening up new avenues treat many different diseases.
Язык: Английский
Процитировано
0
Arabian Journal of Chemistry, Год журнала: 2024, Номер 17(8), С. 105845 - 105845
Опубликована: Май 23, 2024
Cyclopropenone has emerged as a highly versatile precursor in organic synthesis due to its diverse reactivity. The cyclopropenone derivatives could undergo various transformations such cycloaddition reactions, ring-opening and isomerization reactions the presence of different chemical reagents. Over years, significant progress been made manipulation cyclopropenones for construction carbocycles, heterocycles, other useful compounds. Despite several reviews that have concerned chemistry cyclopropenones, utility motifs carbocycles heterocycles rarely reported. Herein, we report recent advancements synthetic precursors towards compounds with biological significance.
Язык: Английский
Процитировано
3
Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(18), С. 4474 - 4487
Опубликована: Янв. 1, 2023
Photogenerated ketenes simplify and accelerate the synthesis of diverse cyclic architectures demonstrate their promising applications in flow chemistry.
Язык: Английский
Процитировано
8