Accessing Functionalized Tetrazines as Click Chemistry Tools: A Synthesis Guide for Chemists and Chemical Biologists DOI Creative Commons
Lucas Moritz Bickem, Katerina Gavriel, Kevin Neumann

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(3)

Published: Nov. 30, 2023

Abstract Since the first report that 1,2,4,5‐tetrazines undergo a bioorthogonal reaction with dienophiles in form of an inverse electron‐demand Diels‐Alder reaction, demand for high‐yielding synthetic approaches towards them grew steadily. Despite this significant interest, tetrazines were predominantly accessed via Pinner synthesis or other Pinner‐like reactions, significantly limiting available substrates. In particular, unsymmetrically substituted s‐tetrazines selective conjugation to another species presented major challenge. To tackle these challenges, new and innovative transformations have been developed widen scope accessible symmetric unsymmetric tetrazines. For instance, Ni(II), Zn(II), sulphur‐catalysed reactions between two nitriles hydrazine developed, which provide access wide range (un‐)symmetric aryl s‐tetrazines. Also, amidines orthoesters give alkyl substituents, whereas usage CH 2 Cl yields valuable H‐monosubstituted Methods using thiocarbohydrazides, terminal fluoroolefins, oxetane esters, tosyl hydrazones are among recent additions. Due high interest tetrazine click‐chemistry approaches, some reach beyond we expect overview routes aid exploration further applications Ultimately, hope guide chemists chemical biologists accessing functional

Language: Английский

Near‐Infrared Light‐Driven Photocatalysis with an Emphasis on Two‐Photon Excitation: Concepts, Materials, and Applications DOI Creative Commons
Chuang Han, Bidyut Kumar Kundu, Yujun Liang

et al.

Advanced Materials, Journal Year: 2023, Volume and Issue: 36(5)

Published: Sept. 13, 2023

Efficient utilization of sunlight in photocatalysis is widely recognized as a promising solution for addressing the growing energy demand and environmental issues resulting from fossil fuel consumption. Recently, there have been significant developments various near-infrared (NIR) light-harvesting systems artificial photosynthesis photocatalytic remediation. This review provides an overview most recent advancements NIR light through creation novel nanostructured materials molecular photosensitizers, well modulating strategies to enhance processes. A special focus given emerging two-photon excitation photocatalysis. The unique features limitations different are critically evaluated. In particular, it highlights advantages utilizing compared UV-visible irradiation one-photon excitation. Ongoing challenges potential solutions future exploration light-responsive also discussed.

Language: Английский

Citations

54

Bioorthogonal chemistry for prodrug activation in vivo DOI
Qunfeng Fu, Siyong Shen, Pengwei Sun

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(22), P. 7737 - 7772

Published: Jan. 1, 2023

Bioorthogonal chemistry used in prodrug activation for cancer treatment and its potential clinical translation.

Language: Английский

Citations

47

Minimalist Tetrazine N-Acetyl Muramic Acid Probes for Rapid and Efficient Labeling of Commensal and Pathogenic Peptidoglycans in Living Bacterial Culture and During Macrophage Invasion DOI Creative Commons

Ashlyn S. Hillman,

Stephen N. Hyland, Kimberly A. Wodzanowski

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(10), P. 6817 - 6829

Published: March 1, 2024

-Acetyl muramic acid (NAM) probes containing alkyne or azide groups are commonly used to investigate aspects of cell wall synthesis because their small size and ability incorporate into bacterial peptidoglycan (PG). However, copper-catalyzed alkyne-azide cycloaddition (CuAAC) reactions not compatible with live cells, strain-promoted (SPAAC) reaction rates modest and, therefore, as desirable for tracking the temporal alterations growth, remodeling, division. Alternatively, tetrazine-

Language: Английский

Citations

10

Low-energy photoredox catalysis DOI
David C. Cabanero, Tomislav Rovis

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Language: Английский

Citations

10

Senolysis Enabled by Senescent Cell‐Sensitive Bioorthogonal Tetrazine Ligation DOI
Mengyang Chang, Yue Dong, Hang Xu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(9)

Published: Jan. 18, 2024

Although the clearance of senescent cells has been proven to slow down aging process and promote anti-cancer chemotherapy, development senolytics remains challenging. Herein, we report a senolytic strategy enabled by cell-sensitive bioorthogonal tetrazine ligation. Our design is based on linking dihydrotetrazine (Tz) galactose (Gal) moiety that serves both as recognition for senescence-associated β-galactosidase caging group control activity. Gal-Tz enables efficient click-release fluorescent hemicyanine doxorubicin from trans-cyclooctene-caged prodrug detect eliminate HeLa A549 over non-senescent counterparts with 16.44 index. Furthermore, leverage selective activation delivery proteolysis-targeting chimeras (PROTACs) senolytics. PROTAC TCO-ARV-771 can be selectively activated delivered into induce degradation bromodomain-containing protein 4. Senolytic PROTACs may offer an way intervention cell senescence thanks their unique capacity degrade target proteins in sub-stoichiometric catalytic fashion. The results this study establish ligation approach viable removal cells.

Language: Английский

Citations

9

Advances in the Synthesis of Bioorthogonal Reagents: s-Tetrazines, 1,2,4-Triazines, Cyclooctynes, Heterocycloheptynes, and trans-Cyclooctenes DOI
Yinzhi Fang,

Ashlyn S. Hillman,

Joseph M. Fox

et al.

Topics in Current Chemistry, Journal Year: 2024, Volume and Issue: 382(2)

Published: May 4, 2024

Language: Английский

Citations

7

Visible and near-infrared light-induced photoclick reactions DOI
Youxin Fu, Nadja A. Simeth, Wiktor Szymański

et al.

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: 8(9), P. 665 - 685

Published: Aug. 7, 2024

Language: Английский

Citations

7

Bioorthogonal Synthetic Chemistry Enabled by Visible‐Light Photocatalysis DOI Creative Commons
José L. Mascareñas, Mauro Mato,

Xulián Fernández-González

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(47)

Published: Aug. 13, 2024

Abstract The field of bioorthogonal chemistry has revolutionized our ability to interrogate and manipulate biological systems at the molecular level. However, range chemical reactions that can operate efficiently in environments without interfering with native cellular machinery, remains limited. In this context, rapidly growing area photocatalysis offers a promising avenue for developing new type tools. inherent mildness, tunability, chemoselectivity, external controllability photocatalytic transformations make them particularly well‐suited applications living systems. This minireview summarizes recent advances technologies, particular focus on their potential enable selective generation designed products within biologically relevant or settings.

Language: Английский

Citations

7

Bioorthogonally activated probes for precise fluorescence imaging DOI Creative Commons
Youxin Fu, Xing Zhang, Luling Wu

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This article provides a comprehensive overview of recent advances in the development bioorthogonally activated probes for labelling and precise situ fluorescence imaging both vitro vivo .

Language: Английский

Citations

7

Triplet‐Triplet Annihilation Upconversion‐Based Photolysis: Applications in Photopharmacology DOI Creative Commons

Maxime Klimezak,

Juliane Chaud,

Anaïs Brion

et al.

Advanced Healthcare Materials, Journal Year: 2024, Volume and Issue: 13(19)

Published: April 13, 2024

The emerging field of photopharmacology is a promising chemobiological methodology for optical control drug activities that could ultimately solve the off-target toxicity outside disease location many drugs treatment given pathology. use photolytic reactions looks very attractive light-activated release but requires to develop sensitive red or near-infrared light excitation better tissue penetration. This review will present concepts triplet-triplet annihilation upconversion-based photolysis and their recent in vivo applications light-induced delivery using photoactivatable nanoparticles.

Language: Английский

Citations

6