Iterative click reactions using trivalent platforms for sequential molecular assembly DOI Creative Commons

Gaku Orimoto,

Suguru Yoshida

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(45), P. 5824 - 5827

Published: Jan. 1, 2024

A facile synthesis of multi(triazole)s by iterative click reactions is disclosed. Diverse multi(triazole)-type mid-molecules can be synthesized easily from readily available modules through good chemoselective reactions.

Language: Английский

Cyclotriphosphazene based materials: Structure, functionalization and applications DOI
Daquan Wang, Xin Xu, Yao Qiu

et al.

Progress in Materials Science, Journal Year: 2024, Volume and Issue: 142, P. 101232 - 101232

Published: Jan. 21, 2024

Language: Английский

Citations

20

Biospecific Chemistry for Covalent Linking of Biomacromolecules DOI Creative Commons
Li Cao, Lei Wang

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(13), P. 8516 - 8549

Published: June 24, 2024

Interactions among biomacromolecules, predominantly noncovalent, underpin biological processes. However, recent advancements in biospecific chemistry have enabled the creation of specific covalent bonds between biomolecules, both vitro and vivo. This Review traces evolution proteins, emphasizing role genetically encoded latent bioreactive amino acids. These acids react selectively with adjacent natural groups through proximity-enabled bioreactivity, enabling targeted linkages. We explore various designed to target different protein residues, ribonucleic acids, carbohydrates. then discuss how these novel linkages can drive challenging properties capture transient protein-protein protein-RNA interactions Additionally, we examine application peptides as potential therapeutic agents site-specific conjugates for native antibodies, highlighting their capacity form stable molecules. A significant focus is placed on reactive therapeutics (PERx), a pioneering technology therapeutics. detail its wide-ranging applications immunotherapy, viral neutralization, radionuclide therapy. Finally, present perspective existing challenges within avenues future exploration advancement this rapidly evolving field.

Language: Английский

Citations

11

Bioinspired Selenium‐Nitrogen Exchange (SeNEx) Click Chemistry Suitable for Nanomole‐Scale Medicinal Chemistry and Bioconjugation DOI
Wei Hou, Yiyuan Zhang,

Fuchao Huang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(15)

Published: Feb. 12, 2024

Abstract Click chemistry is a powerful molecular assembly strategy for rapid functional discovery. The development of click reactions with new connecting linkage great importance expanding the toolbox. We report first selenium‐nitrogen exchange (SeNEx) reaction between benzoselenazolones and terminal alkynes (Se−N to Se−C), which inspired by biochemical SeNEx Ebselen cysteine (Cys) residue Se−S). formed selenoalkyne connection readily elaborated, thus endowing this multidimensional diversity. Besides, modular, predictable, high‐yielding, features fast kinetics (k2≥14.43 M −1 s ), excellent group compatibility, works well at miniaturization (nanomole‐scale), opening up many interesting opportunities organo‐Se synthesis bioconjugation, as exemplified sequential (coupled ruthenium‐catalyzed azide‐alkyne cycloaddition (RuAAC) sulfur‐fluoride (SuFEx)), selenomacrocycle synthesis, nanomole‐scale Se‐containing natural product library DNA‐encoded (DEL), late‐stage peptide modification ligation, multiple functionalization proteins. These results indicated that useful developments, established will serve transformative platform in multidisciplinary fields such synthetic chemistry, material science, chemical biology, medical drug

Language: Английский

Citations

10

Genetically enabling phosphorus fluoride exchange click chemistry in proteins DOI Creative Commons
Li Cao, Bingchen Yu, Shanshan Li

et al.

Chem, Journal Year: 2024, Volume and Issue: 10(6), P. 1868 - 1884

Published: March 5, 2024

Phosphorus fluoride exchange (PFEx), recently debuted in small molecules, represents the forefront of click chemistry. To explore PFEx's potential biological settings, we developed amino acids phosphoramidofluoridate tyrosine (PFY) and lysine (PFK) featuring phosphoramidofluoridates incorporated them into proteins through genetic code expansion. PFY/PFK selectively reacted with nearby His, Tyr, Lys, or Cys proteins, both vitro living cells, demonstrating that proximity enabled PFEx reactivity without external reagents. The reaction His showed unique pH-dependent properties created thermally sensitive linkages. Additionally, Na2SiO3 enhanced reactions Tyr Cys. PFEx, by generating defined covalent P-N/O linkages, extends utility phosphorus linkages aligning nature's use phosphate connectors other biomolecules. More versatile durable than sulfur (SuFEx), expands latent bioreactive arsenal for protein engineering will facilitate broad application this potent chemistry biomedical fields.

Language: Английский

Citations

8

What is the future of click chemistry in drug discovery and development? DOI
Ana Carolina Amorim Orrico, Anthony J. Burke

Expert Opinion on Drug Discovery, Journal Year: 2024, Volume and Issue: 19(3), P. 267 - 280

Published: Jan. 12, 2024

Introduction The concept of click chemistry was introduced in 2001 as an effective, efficient, and sustainable approach to making functional groups harnessing the thermodynamic properties a set known chemical reactions that are based on nature. Some most common examples include produce 1,2,3-triazoles, which have been used with great success drug discovery development, biology. unite two molecules quickly irreversibly, can be performed inside living cells, without harming cell.

Language: Английский

Citations

6

Modular synthesis of functional libraries by accelerated SuFEx click chemistry DOI Creative Commons
Joshua A. Homer, Rebecca A. Koelln, Andrew S. Barrow

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(11), P. 3879 - 3892

Published: Jan. 1, 2024

The Accelerated SuFEx Click Chemistry (ASCC) protocol, adapted to a 96-well plate format, has been applied the late-stage derivatization of bioactive molecules and array synthesis anticancer agents, showcasing its potential for drug discovery.

Language: Английский

Citations

6

Bioorthogonal Bond Cleavage Chemistry for On-demand Prodrug Activation: Opportunities and Challenges DOI
Qingqiang Min, Xingyue Ji

Journal of Medicinal Chemistry, Journal Year: 2023, Volume and Issue: 66(24), P. 16546 - 16567

Published: Dec. 12, 2023

Time- and space-resolved drug delivery is highly demanded for cancer treatment, which, however, can barely be achieved with a traditional prodrug strategy. In recent years, the strategy based on bioorthogonal bond cleavage chemistry has emerged advantages of high temporospatial resolution over activation homogeneous irrespective individual heterogeneity. past five tremendous progress been witnessed in this field one such entering Phase II clinical trials. This Perspective aims to highlight these new advances (2019–2023) critically discuss their pros cons. addition, remaining challenges potential strategic directions future will also included.

Language: Английский

Citations

12

Phosphorus Fluoride Exchange (PFEx) Click Chemistry: 2‐Substituted‐alkynyl‐1‐cyclotriphosphazene (SACP) Hubs for Diversity Oriented Clicking DOI Open Access
Zifei Wang, Dharmendra S. Vishwakarma, Shoujun Sun

et al.

Advanced Synthesis & Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 8, 2025

Abstract Phosphorus Fluoride Exchange (PFEx) is a new click chemistry technology that hinges on the creation of innovative hubs to unlock its potential and broaden applications. In this study, we outline some guiding principles for PFEx hub development validate these by developing hub, 2‐substituted‐alkynyl‐1‐cyclotriphosphazenes (SACPs). These SACPs serve as versatile with stable functionality orthogonal reactivity, exemplifying their utility within Diversity Oriented Clicking (DOC) framework. We demonstrate interact various 1,3‐dipoles, enabling synthesis phosphorus‐rich compounds through sequential cycloaddition reactions, thus pioneering synthetic routes wide application chemistry.

Language: Английский

Citations

0

Advances in sulfur fluoride exchange for chemical biology DOI
Tobias Hansen,

Marcos San Segundo,

Annika M. Mergel

et al.

Trends in Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0

Engineered Polymeric Microspheres with Synergistic Hydrogen‐Bonding Nanotraps and Multisite Adsorption for Ultrafast Herbicide Decontamination DOI Open Access

Jicai Jiang,

Haibo Wan,

Jinchang Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

The ultrafast removal of trace herbicides like paraquat (PQ) and diquat (DQ) from water is urgent yet challenging due to their highwater stability strong binding properties. Here, efficient PQ DQ based on hydrogen-bonding nanotraps dominant multi-site adsorption were developed. Two crosslinked polymeric microspheres, βCD-PF γCD-PF, synthesized cyclodextrins (CDs) hexafluorocyclotriphosphazene (HFP). γCD-PF microsphere with sufficient hydrogen bonding the pore surface prompts kinetics constants up 127.09 192.64 g mg-1 min-1, achieving 99% efficiency for within 5 s. exhibits exceptional selectivity over larger competing dyes. Importantly, (1 ppm) can be effectively treated achieve a concentration far below U.S. EPA standard (0.003 30 seconds. driven by mechanism: electrostatic π-π interactions HFP promote adsorbate accumulation CD surface, while high-density in enhance bond strength, enabling rapid capture. This work provides valuable strategy designing adsorbents effective herbicide water.

Language: Английский

Citations

0