Recent Advances in the Development of Targeted Activation Strategies for Organoboron Prodrugs DOI Open Access

Moyi Liu,

Taotao Zou

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 27, 2024

Abstract Elevated levels of reactive oxygen species (ROS) are a hallmark varieties diseases such as cancer, inflammation, and neurodegenerative disorders. Inspired by the discrepancy ROS concentrations between pathological tissues normal counterparts, an increasing number ROS‐responsive theragnostic prodrugs developed in past years, with particularly high proportions organoboron‐based that can respond to H 2 O . Unfortunately, studies have demonstrated intrinsic (H ) most tissue only slightly higher than not adequate activate organoboron prodrugs; contrast, several compounds been clinically approved which boronic acid acts electrophilic warhead. To this end, developing more robust universal approaches for acid‐prodrug activation becomes highly attractive. In context, we discuss recently reported strategies boron‐caged particular focus on their design principles mechanisms. The perspectives future directions important research area discussed well.

Language: Английский

Multiscale photocatalytic proximity labeling reveals cell surface neighbors on and between cells DOI
Zhi Lin, Kaitlin Schaefer, Irene Lui

et al.

Science, Journal Year: 2024, Volume and Issue: 385(6706)

Published: July 18, 2024

Proximity labeling proteomics (PLP) strategies are powerful approaches to yield snapshots of protein neighborhoods. Here, we describe a multiscale PLP method with adjustable resolution that uses commercially available photocatalyst, Eosin Y, which upon visible light illumination activates different photo-probes range radii. We applied this platform profile neighborhoods the oncogenic epidermal growth factor receptor and orthogonally validated more than 20 neighbors using immunoassays AlphaFold-Multimer prediction. further profiled cell-cell synapses induced by bispecific T cell engagers chimeric antigen cells. This integrated maps local distal networks on between surfaces, will aid in systematic construction surface interactome, revealing horizontal signaling partners reveal new immunotherapeutic opportunities.

Language: Английский

Citations

24
Robust Miniemulsion PhotoATRP Driven by Red and Near-Infrared Light DOI Creative Commons
Xiaolei Hu, Rongguan Yin, Jaepil Jeong

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(19), P. 13417 - 13426

Published: May 1, 2024

Photoinduced polymerization techniques have gathered significant attention due to their mild conditions, spatiotemporal control, and simple setup. In addition homogeneous media, efforts been made implement photopolymerization in emulsions as a practical greener process. However, previous photoinduced reversible deactivation radical (RDRP) heterogeneous media has relied on short-wavelength lights, which limited penetration depth, resulting slow relatively poor control. this study, we demonstrate the first example of highly efficient miniemulsion ATRP open air driven by red or near-infrared (NIR) light. This was facilitated utilization water-soluble photocatalyst, methylene blue (MB+). Irradiation red/NIR light allowed for excitation MB+ subsequent photoreduction deactivator presence electron donors initiate mediate The NIR light-driven photoATRP provided successful synthesis polymers with low dispersity (1.09 ≤ Đ 1.29) quantitative conversion within an hour. study further explored impact kinetics reactors varying sizes large-scale reaction (250 mL), highlighting advantages longer-wavelength light, particularly dispersed owing its superior penetration. work opens new avenues robust emulsion techniques, offering more approach improved control efficiency.

Language: Английский

Citations

16
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
Synthesis, Characterization, and Catalytic Activity of Ni(0) (DQ)dtbbpy, an Air-Stable, Bifunctional Red-Light-Sensitive Precatalyst DOI
Jingsheng Li, Pengpeng Wang, Bing Bai

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 5, 2025

Despite a well-established and growing body of work on nickel(0) precatalysts, the potential complexes as bifunctional precatalysts remains underexplored. In this study, we synthesized, characterized, evaluated catalytic activity (Ni(0)(DQ)dtbbpy), bifunctional, red-light-sensitive, air-stable complex. Owing to its unique photophysical properties, it effectively catalyzed etherification amination aryl bromides under 620–630 nm light irradiation, functioning both photocatalyst an active metal catalyst. Mechanistic studies density functional theory (DFT) calculations further confirmed exceptional absorption properties Ni(0)(DQ)dtbbpy in red-light region, well electron transfer process triggered by irradiation.

Language: Английский

Citations

1
Deep-Red and Ultrafast Photocatalytic Proximity Labeling Empowered In Situ Dissection of Tumor-Immune Interactions in Primary Tissues DOI

Zhizheng Lou,

Yan Zhang, Xuan Liang

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 4, 2025

Immunotherapy efficacy in solid tumors varies greatly, influenced by the tumor microenvironment (TME) and dynamic tumor-immune interactions within it. Decoding these situ with minimal interference native tissue architecture delicate immune responses is critical for understanding progression optimizing therapeutic strategies. Here, we introduce CAT-Tissue, a novel deep-red photocatalytic proximity labeling method that enables ultrafast, high-resolution profiling of primary tissues. By leveraging nanobody-Chlorin e6 as photocatalyst biotin-aniline probe, CAT-Tissue enabled rapid comprehensive detection various both coculture systems sections. Coupled bulk RNA-sequencing, revealed distinct gene expression patterns between tumor-neighboring tumor-distal lymphocytes, highlighting recognition CD8+ T cells, which exhibited activated, effector, exhausted phenotypes. cell strategy excellent penetration biocompatibility, offers nongenetically encoded platform high sensitivity spatiotemporal controllability complex environments situ, may advance our immunology guide development more effective immunotherapies.

Language: Английский

Citations

1
Multiprobe Photoproximity Labeling of the EGFR Interactome in Glioblastoma Using Red-Light DOI
Feifei Tong, Weidong Zhou, Michalina Janiszewska

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Photocatalytic proximity labeling has emerged as a valuable technique for studying interactions between biomolecules in cellular context, providing precise spatiotemporal control over protein labeling. One significant advantage of these methods is their modularity, allowing the use single photocatalyst with different reactive probes to expand interactome coverage and capture diverse interactions. Despite advances, fewer have been developed using red-light excitation, limiting photoproximity more complex media such tissues animal models. Herein, we develop platform under utilizing catalyst two distinct probe types. We first design carbene based system that utilizes sulfonium diazo probes. This successfully applied on A549 cells epidermal growth factor receptor (EGFR) Cetuximab-Chlorin e6 conjugate. Benchmarking against established techniques indicates this approach performs comparably leading carbene-based methods. Next, leverage strong singlet oxygen generation (SOG) ability Chlorin establish an alternative aniline hydrazide EGFR directed chemoproteomics experiments reveal overlap system, capturing subset identified by SOG system. Finally, deploy our characterization resected human glioblastoma (GBM) tissue samples removed from locations same tumor, representing tumor's infiltrating edge its viable center, identifying several GBM specific interacting proteins may serve launch point future therapeutic campaigns.

Language: Английский

Citations

1
Recent advancements in the molecular design of deep-red to near-infrared light-absorbing photocatalysts DOI
Minling Zhong, Yujie Sun

Chem Catalysis, Journal Year: 2024, Volume and Issue: 4(8), P. 100973 - 100973

Published: April 17, 2024

Language: Английский

Citations

7
Diazirine-Functionalized Polyurethane Crosslinkers for Isocyanate-Free Curing of Polyol-Based Coatings DOI Creative Commons
Felix J. de Zwart, Lukas A. Wolzak, Keimpe J. van den Berg

et al.

ACS Applied Polymer Materials, Journal Year: 2024, Volume and Issue: 6(6), P. 3517 - 3522

Published: March 5, 2024

Polyurethane coatings have strong material properties due to the hydrogen bonding inherent urethane groups. However, installing this moiety usually requires curing through difficult-to-handle isocyanates. In work, we show development of a polyurethane-based crosslinker that can be used formulate one-component polyurethane coating with similar those isocyanate-based coatings. To achieve this, diazirine functionalities generate carbenes upon heating, which react alcohol in polyol crosslinked network high storage modulus.

Language: Английский

Citations

4
Near-infrared light activatable nanoplatform for proteins labeling, enrichment and visualization in living systems DOI
Peng Liu, Shengli Zhang, Tingting Zhang

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110966 - 110966

Published: Feb. 1, 2025

Language: Английский

Citations

0
Photolytic Access to Oxaspirodecanes and Chromenes from Vinyldiazo Ester Cycloaddition with p-Quinones: A Vinylcarbene Is Not Involved DOI

Soumen Biswas,

Ramon Trevino,

Seth O. Fremin

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

Synthetic methods that provide access to skeletally diverse heterocyclic motifs are poised accelerate drug discovery and streamline the synthesis of advanced intermediates materials. However, development such synthetic necessitates leveraging previously unexplored mechanistic pathways. We report herein an efficient blue light-emitting diode light-induced reaction vinyldiazoacetates quinones produces spirocyclic dihydrofurans, featuring synthetically challenging oxaspiro[4,5]decane core numerous medicinal agents, agrochemicals, natural products. In a departure from well-established photochemical reactivity diazo compounds, these reactions do not involve vinylcarbene formed by photolytic dinitrogen extrusion. Instead, they result photoexcitation quinone its triplet state with subsequent energy transfer vinyldiazo ester. The addition vinylogous carbon vinyldiazoacetate oxygen affords diradical collapses dihydrofuran upon loss dinitrogen. A strain release-driven Bro̷nsted acid-catalyzed rearrangement products unravels fused bicyclic ring system equally medicinally valuable chromenes, enabling facile skeletal diversification important motifs.

Language: Английский

Citations

0