Co‐aggregation as A Simple Strategy for Preparing Fluorogenic Tetrazine Probes with On‐Demand Fluorogen Selection** DOI Open Access
S. Segawa, Jiajie Wu, Ryan T. K. Kwok

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(11)

Published: Dec. 7, 2023

Abstract Life science has progressed with applications of fluorescent probes—fluorophores linked to functional units responding biological events. To meet the varied demands across experiments, simple organic reactions connect fluorophores and have been developed, enabling on‐demand selection fluorophore‐functional unit combinations. However, synthesis requires professional equipment skills, standing as a daunting task for life scientists. In this study, we present simple, fast, convenient strategy probe preparation: co‐aggregation hydrophobic molecules. We focused on tetrazine—a difficult‐to‐prepare yet useful that provides effective bioorthogonal reactivity strong fluorogenicity. Simply mixing tetrazine molecules aggregation‐induced emission (AIE) luminogens in water, is induced, AIE quenched. Subsequent click reaction bioorthogonally turns emission, identifying these coaggregates fluorogenic probes. Thanks fluorogenicity, established new time‐gated fluorescence bioimaging technique distinguish overlapping signals, multi‐organelle imaging two same‐color fluorophores. Our study showcases potential method preparation probes well protocols molecular design principles approach, offering an solution evolving needs research.

Language: Английский

Matthew effect: General design strategy of ultra‐fluorogenic nanoprobes with amplified dark–bright states in aggregates DOI Creative Commons
S. Segawa, Xinwen Ou, Tianruo Shen

et al.

Aggregate, Journal Year: 2024, Volume and Issue: 5(2)

Published: Jan. 4, 2024

Abstract Fluorescence imaging, a key technique in biological research, frequently utilizes fluorogenic probes for precise imaging living systems. Tetrazine is an effective emission quencher probe designs, which can be selectively damaged upon bioorthogonal click reactions, leading to considerable enhancement. Despite significant efforts increase the enhancement ratio ( I AC / BC ) of tetrazine‐functionalized probes, influence molecular aggregation on properties has been largely overlooked these designs. In this study, we reveal that ultrahigh realized aggregate system when tetrazine paired with aggregation‐induced (AIE) luminogens. amplifies its quenching efficiency and drastically reduce background emissions. Subsequent reactions damage trigger AIE, considerably enhanced . We further showcase capability ultra‐fluorogenic systems selective multiple organelles cells. term unique fluorogenicity AIE luminogen‐quencher complexes amplified dark‐bright states as “Matthew effect” emission, potentially providing universal approach attain diverse

Language: Английский

Citations

10
Unveiling the photophysical mechanistic mysteries of tetrazine-functionalized fluorogenic labels DOI Creative Commons
Tianruo Shen, Xiaogang Liu

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Tetrazine-based fluorogenic labels are widely utilized in medical and biological studies, exhibiting substantial fluorescence enhancement (FE) following tetrazine degradation through bio-orthogonal reactions. However, the underlying mechanisms driving this response remain only partially resolved, particularly regarding diminished FE efficiency deep-red near-infrared (NIR) regions. This knowledge gap has impeded efforts to optimize these for extended emission wavelengths improved ratios. review offers a photophysical perspective, discussing quenching pathways (i.e., energy flows charge separation) that regulate properties exhibited various types of labels. Moreover, work examines emerging role intramolecular rotations certain tetrazine-based structures integration additional quencher units. The proposed alternative channel potential surpass traditional wavelength constraints while achieving FE. By examining mechanisms, aims advance understanding tetrazine-functionalized provide guiding principles their future design practical applications.

Language: Английский

Citations

0
Aggregation-Induced Emission-Based Chemiluminescence Systems in Biochemical Analysis and Disease Theranostics DOI Creative Commons
Yixin Shi, Xuewen He

Molecules, Journal Year: 2024, Volume and Issue: 29(5), P. 983 - 983

Published: Feb. 23, 2024

Chemiluminescence (CL) is of great significance in biochemical analysis and imaging due to its high sensitivity lack need for external excitation. In this review, we summarized the recent progress AIE-based CL systems, including their working mechanisms applications analysis, bioimaging, disease diagnosis treatment. ion molecular detection, shows selectivity sensitivity, especially detection dynamic reactive oxygen species (ROS). Further, integrated NIR-CL single-molecule system nanostructural platform harnessing resonance energy transfer (CRET) have remarkable advantages long-term with superior capability penetrating deep tissue depth signal-to-noise ratio, are promising vivo image-guided therapy. Finally, shortcomings existing AIE-CL provided our perspective on possible ways develop more powerful systems future. It can be highly expected that these promoted will play bigger roles theranostics.

Language: Английский

Citations

2
Co‐aggregation as A Simple Strategy for Preparing Fluorogenic Tetrazine Probes with On‐Demand Fluorogen Selection** DOI
S. Segawa, Jiajie Wu, Ryan T. K. Kwok

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(11)

Published: Dec. 7, 2023

Life science has progressed with applications of fluorescent probes-fluorophores linked to functional units responding biological events. To meet the varied demands across experiments, simple organic reactions connect fluorophores and have been developed, enabling on-demand selection fluorophore-functional unit combinations. However, synthesis requires professional equipment skills, standing as a daunting task for life scientists. In this study, we present simple, fast, convenient strategy probe preparation: co-aggregation hydrophobic molecules. We focused on tetrazine-a difficult-to-prepare yet useful that provides effective bioorthogonal reactivity strong fluorogenicity. Simply mixing tetrazine molecules aggregation-induced emission (AIE) luminogens in water, is induced, AIE quenched. Subsequent click reaction bioorthogonally turns emission, identifying these coaggregates fluorogenic probes. Thanks fluorogenicity, established new time-gated fluorescence bioimaging technique distinguish overlapping signals, multi-organelle imaging two same-color fluorophores. Our study showcases potential method preparation probes well protocols molecular design principles approach, offering an solution evolving needs research.

Language: Английский

Citations

6
Improved thermal properties of polydimethylsiloxane by copolymerization and thiol–ene crosslinking of 2-pyrone-4,6-dicarboxylic acid moiety DOI Creative Commons

Tetsuo Shimura,

Yijie Jin, Keiichi Kuboyama

et al.

Polymer Chemistry, Journal Year: 2024, Volume and Issue: 16(1), P. 45 - 51

Published: Nov. 25, 2024

Thermally stable copolymers of 2-pyrone-4,6-dicarboxylic acid (PDC), a metabolic intermediate lignin, and polydimethylsiloxane were synthesized cross-linked by using thiol–ene click chemistry.

Language: Английский

Citations

0
Cutting-edge bioorthogonal chemistry: Innovations, practical applications, and emerging trends DOI Open Access
Anup Basnet Chetry

European Journal of Chemistry, Journal Year: 2024, Volume and Issue: 15(4), P. 355 - 365

Published: Dec. 31, 2024

Bioorthogonal chemistry has emerged as a pivotal field in molecular science, offering transformative tools for applications drug discovery, imaging, and biology. This review provides comprehensive analysis of recent advancements bioorthogonal chemistry, emphasizing key innovations, practical applications, future research directions. We explore state-of-the-art reactions, including Staudinger ligation, strain-promoted azide-alkyne cycloaddition (SPAAC), tetrazine detailing their mechanisms, advantages, limitations. The highlights significant innovations such novel fluorogenic probes, improved catalysts, enhanced reaction conditions that have expanded the utility efficiency these reactions. Practical are examined, showing how advances revolutionized fields like live-cell targeted delivery, labeling. Looking to future, we discuss emerging trends potential avenues, integration with other advanced technologies development new methodologies. detailed overview current state outlines its potential, serving valuable resource researchers practitioners field.

Language: Английский

Citations

0
Co‐aggregation as A Simple Strategy for Preparing Fluorogenic Tetrazine Probes with On‐Demand Fluorogen Selection** DOI Open Access
S. Segawa, Jiajie Wu, Ryan T. K. Kwok

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(11)

Published: Dec. 7, 2023

Abstract Life science has progressed with applications of fluorescent probes—fluorophores linked to functional units responding biological events. To meet the varied demands across experiments, simple organic reactions connect fluorophores and have been developed, enabling on‐demand selection fluorophore‐functional unit combinations. However, synthesis requires professional equipment skills, standing as a daunting task for life scientists. In this study, we present simple, fast, convenient strategy probe preparation: co‐aggregation hydrophobic molecules. We focused on tetrazine—a difficult‐to‐prepare yet useful that provides effective bioorthogonal reactivity strong fluorogenicity. Simply mixing tetrazine molecules aggregation‐induced emission (AIE) luminogens in water, is induced, AIE quenched. Subsequent click reaction bioorthogonally turns emission, identifying these coaggregates fluorogenic probes. Thanks fluorogenicity, established new time‐gated fluorescence bioimaging technique distinguish overlapping signals, multi‐organelle imaging two same‐color fluorophores. Our study showcases potential method preparation probes well protocols molecular design principles approach, offering an solution evolving needs research.

Language: Английский

Citations

0