Designing Bioorthogonal Reactions for Biomedical Applications

Research, Journal Year: 2023, Volume and Issue: 6

Published: Jan. 1, 2023

Bioorthogonal reactions are a class of chemical that can be carried out in living organisms without interfering with other reactions, possessing high yield, selectivity, and efficiency. Since the first proposal conception by Professor Carolyn Bertozzi 2003, bioorthogonal chemistry has attracted great attention been quickly developed. As an important biology tool, have applied broadly biomedicine, including bio-labeling, nucleic acid functionalization, drug discovery, activation, synthesis antibody-drug conjugates, proteolysis-targeting chimeras. Given this, we summarized basic knowledge, development history, research status, prospects their biomedical applications. The main purpose this paper is to furnish overview intriguing variety applications provide guidance for design novel enrich toolkits.

Language: Английский

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Enantioselective synthesis of 3a-azido-pyrroloindolines by copper-catalyzed asymmetric dearomative azidation of tryptamines

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(50), P. 7831 - 7834

Published: Jan. 1, 2023

Copper-catalyzed asymmetric dearomative azidation of tryptamines using azidobenziodoxolone as an azidating reagent was developed, which affords a variety 3a-azido-pyrroloindolines in good to high enantioselectivities under mild reaction conditions. The azides could be readily transformed into the corresponding 3a-amino-pyrroloindolines via reduction and 1,2,3-triazole derivatives click reaction.

Language: Английский

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Synthesis of Highly Stable and Reactive Nitrile N-Oxides and Their Application as Catalyst-Free Crosslinkers

Macromolecules, Journal Year: 2023, Volume and Issue: 56(12), P. 4715 - 4726

Published: June 5, 2023

Nitrile N-oxide-based click ligation is a very promising technique for polymer crosslinking due to the unique advantages of catalyst-free and byproduct-free reactions. For this technique, nitrile N-oxides that are sufficiently stable at room temperature have high reactivity under mild conditions desirable. Usually, neighboring bulky substituents introduced enhance stability N-oxides, which however bring down steric hindrance. Herein, methyl groups, small-sized substituents, were into o,o′-positions phenyl enable reactivity. Thus, several novel aromatic synthesized. Among them, ditopic prepared through three simple steps including etherification, oximation, oxidative dehydrogenation, whereas tritopic synthesized by directly introducing N-oxide functionality corresponding trifunctional compounds avoid undesirable side These as reagents exhibited reactivity, efficient natural rubber was achieved give elastomers with good mechanical properties, revealing potential such useful crosslinkers unsaturated bond-containing polymers. This work provides reliable synthesis ditopic/tritopic broadening application toward crosslinking.

Language: Английский

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The Cyanopyridine–Aminothiol Click Reaction: Expanding Horizons in Chemical Biology

Synlett, Journal Year: 2023, Volume and Issue: 35(10), P. 1067 - 1071

Published: Nov. 20, 2023

Abstract Bioorthogonal reactions hold significant promise for applications in chemical biology. Despite their potential, nitriles have often been overlooked as reactive functional groups selective bioconjugation. The condensation reaction between cyanopyridines and 1,2-aminothiols stands out a particularly favorable nitrile modification strategy that proceeds under biocompatible conditions. Cyanopyridines can be seamlessly incorporated into peptides proteins through both biotechnological approaches. Similarly, the integration of is achievable, leveraging uniquely N-terminal cysteine group. 1 Introduction 2 Biocompatible Condensation Reaction 3 Peptide Macrocyclisation 4 Orthogonality to Cysteine 5 Combination with Genetic Encoding 6 Conclusion

Language: Английский

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Novel Oleanolic Acid-Phtalimidines Tethered 1,2, 3 Triazole Hy-Brids As Promising Antibacterial Agents: Design, Synthesis, In Vitro Experiments and In Silico Docking Studies

Published: May 23, 2023

As part of valorisation agricultural waste into bioactive compounds, a series structurally novel oleanolic acid ((3β-hydroxyolean-12-en-28-oic acid, OA-1)-phtalimidines (isoindolinones) conjugates 18a-v bearing 1,2,3-triazole moieties were designed and synthesized by treating previously azide 4 prepared from OA-1 isolated olive pomace (Olea europaea L.) with wide range propargylated phtalimidines using the Cu(I)-catalyzed click chemistry approach. its newly analogues screened in vitro for their antibacterial activity against two Gram-positive bacteria, Staphylococcus aureus Listeria monocytogenes; Gram-negative Salmonella thyphimurium Pseudomonas aeruginosa. Attractive results obtained notably L. monocytogenes. Compounds 18d, 18g 18h exhibited highest when compared other compounds tested pathogenic bacterial strains. Molecular docking study was performed to explore binding mode most active derivatives target protein Results showed importance both hydrogen bonding hydrophobic interactions are favor experimental data.

Language: Английский

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Alkynylated and triazole-linked aroyl-S,N-ketene acetals: one-pot synthesis of solid-state emissive dyes with aggregation-induced enhanced emission characteristics

Scientific Reports, Journal Year: 2023, Volume and Issue: 13(1)

Published: Sept. 1, 2023

Alkynylated aroyl-S,N-ketene acetals are readily synthesized in mostly excellent yields by a Sonogashira reaction resulting substance library of more than 20 examples. Upon expansion the sequence deprotection and concatenating copper-click one-pot fashion, 11 triazole-ligated is accessible. All derivatives show pronounced solid-state emission aggregation-induced properties depending on nature alkynyl or triazole substituents.

Language: Английский

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Klik kimika: erabilera askotariko Nobel saridun erreakzioa

EKAIA Euskal Herriko Unibertsitateko Zientzi eta Teknologi Aldizkaria, Journal Year: 2024, Volume and Issue: 46, P. 87 - 107

Published: Feb. 12, 2024

2022ko Kimikako Nobel saria Carolyn R. Bertozzik, Morten Meldalek eta Karl B. Sharplessek jaso zuten, konposatu desberdinak modu azkar eraginkorrean egiteko prozedura berria garatu zutelako, klik kimika deritzona. Klik erreakzioek hainbat abantaila aurkezten dituzte: adibidez, esperimentalki errazak dira, erreakzio baldintza anitz toleratzen dituzte, oso selektiboak erregioespezifikoak dira etekin kuantitatiboak ematen dituzte. Gainera, ez oxigenoarekiko urarekiko sentikorrak, isolatze etapa erraza duten erreakzioak dira. Horretaz gain, lau talde nagusitan banatu daitezke: ordezkapen nukleozalea, zikloadizioak, karboniloen ez-aldolikoak C-C lotura anizkoitzen gaineko adizio erreakzioak. Aipatutako baldintzak betetzen dituzten erreakzioen artean, kobrez katalizaturiko azida alkino 1,3-zikloadizioa ezagunena da. Izan ere, erabilia izan da eremutan, hala nola, materialen kimikan, biokimikan edo medikoan. Esate baterako, aktibitate biologikoa molekulak gainazal metaliko polimerikoen gainean biokonjugatzeko, farmako berriak garatzeko, propietate hobeak material termoegonkorrak garatzeko katalizatzaile gisa erabil daitezkeen hidrogelak eratzeko erabili ohi Bertozzik aurrerago eraman zuen, sistema biologikoetan ahal den kobrerik gabeko erreakzioa bio-ortogonala sortuz. Horretarako, zitotoxikoa kobre katalizatzailea baztertu zuen alkinoen erreaktibitatea areagotzen duen prozeduran oinarrituz. Are gehiago, hau biomolekulen minbizi-zelulen markatze kobalenterako zelula biziak erabiliz; baita minbiziaren kontrako farmakoak daramatzaten nanopartikulak tumorea selektiboki metatzeko estrategia bezala ere.

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Unveiling the secrets using bioorthogonal chemistry to explore the impact of adipokines on male reproduction and infertility

Journal of Molecular Chemistry., Journal Year: 2024, Volume and Issue: 4(1)

Published: Jan. 31, 2024

Adipocytes secrete bioactive peptides known as adipokines, which have diverse physiological functions related to metabolic homeostasis, inflammation, and energy regulation. However, the precise involvement of adipokines in intricate processes male reproductive function is not well understood. This review article provides a comprehensive overview recent advancements field bioorthogonal chemistry, powerful set techniques used study signaling mechanisms underlying effects on health infertility. By employing advanced chemistry methods, researchers started unravel hidden molecular interactions between tissues. Through use probes such clickable small molecules, labeling, genetically encoded unnatural amino acids, scientists gained unprecedented insight into spatial temporal dynamics adipokine within system. The emphasizes important studies that elucidated impact crucial reproduction, including spermatogenesis, sperm quality, hormone production, testicular function. Furthermore, it explores emerging role infertility, providing insights potential therapeutic strategies for addressing dysfunction associated with adiposity-related disorders. Overall, this highlights pivotal uncovering through exert their influence physiology pathology. combination research holds great promise unraveling mysteries thus opening up new avenues diagnosing treating infertility disturbances. URN:NBN:sciencein.jmc.2024.681

Language: Английский

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Synthesis of 4-(3-(1-substituted/unsubstituted-phenyl-1H-1,2,3-triazole-4-yl)propoxy)benzaldehydes: In vitro antimicrobial, antimalarial activities and In silico docking study

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1317, P. 139006 - 139006

Published: June 18, 2024

Language: Английский

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Saturated Heterocyclic Sulfamoyl Fluorides: Building Blocks for the SuFEx Chemistry

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(42)

Published: July 30, 2024

Abstract A scalable protocol for direct SO 2 F ‐based fluorosulfonylation of saturated (hetero)cyclic and functionalized amines is reported. The method cost‐effective applicable multigram preparation structurally diverse compounds, as illustrated by the synthesis 58 building blocks decorated with common functional groups. comparison overall yields products demonstrates advantages present over alternative approaches. obtained sp 3 ‐enriched sulfamoyl fluorides can be considered a new generation SuFEx (sulfur fluoride exchange) chemistry. synthetic utility synthesized was demonstrated late‐stage reactions tolerating functionality well transformations to provide corresponding sulfamide, sulfamate, sulfonamide derivatives.

Language: Английский

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