Effect of Two-Photon Excitation to 8-Azacoumarin Derivatives as Photolabile Protecting Groups DOI Open Access
Takuya Kobayakawa,

Hikaru Takano,

Takahiro Ishii

et al.

Chemical and Pharmaceutical Bulletin, Journal Year: 2024, Volume and Issue: 72(3), P. 311 - 312

Published: March 15, 2024

An improvement of the two-photon excitation was achieved using 8-azacoumarin-type caged compounds, which showed large values uncaging action cross-section (δu >0.1 Goeppert–Mayer (GM)). In particular, 7-hydroxy-6-iodo-8-azacoumarin (8-aza-Ihc)-caged compound an excellent value = 1.28 GM). Therefore, photolabile protecting groups (PPGs) can be used as sources.

Language: Английский

Enhancing Precision in Photodynamic Therapy: Innovations in Light-Driven and Bioorthogonal Activation DOI Creative Commons
Natalia S. Kuzmina, E. A. Fedotova, Petar Jankovic

et al.

Pharmaceutics, Journal Year: 2024, Volume and Issue: 16(4), P. 479 - 479

Published: March 31, 2024

Over the past few decades, photodynamic therapy (PDT) has evolved as a minimally invasive treatment modality offering precise control over cancer and various other diseases. To address inherent challenges associated with PDT, researchers have been exploring two promising avenues: development of intelligent photosensitizers activated through light-induced energy transfers, charges, or electron disruption photosensitive bonds. Moreover, there is growing emphasis on bioorthogonal delivery activation within tumors, enabling targeted deployment these systems in specific tissues, thus achieving highly PDT. This concise review highlights advancements made last decade realm light-activated photosensitizers, comparing their efficacy shaping future directions advancement therapy.

Language: Английский

Citations

3

Spatio-temporal control of mitosis using light via a Plk1 inhibitor caged for activity and cellular permeability DOI Creative Commons
Victoria von Glasenapp, Ana C. Almeida, Dalu Chang

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Feb. 19, 2025

Abstract The ability to control the activity of kinases spatially and temporally is essential elucidate role signalling pathways in development physiology. Progress this direction has been hampered by lack tools manipulate kinase a highly controlled manner vivo. Here we report strategy modify BI2536, well characterized inhibitor conserved mitotic Polo-like 1 (Plk1). We introduce same coumarin photolabile protecting group (PPG) at two positions inhibitor. At one position, prevents interaction with Plk1, second it masks an added carboxylic acid, important for cellular retention. Exposure light results removal both PPGs, leading activation its trapping inside cells. demonstrate efficacy caged three-dimensional spheroid cultures: uncaging single pulse, can inhibit Plk1 arrest cell division, dynamic process, spatio-temporal control. Our design be applied other small molecules, providing solution their living cells unprecedented precision.

Language: Английский

Citations

0

A Structurally Compact Aqueous Soluble Oxypicolinium Photocage with High Photosensitivity DOI Creative Commons

Komadhie C. Dissanayake,

Mohammad K. I. Walid,

Madelyn Austin

et al.

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

Published: Jan. 1, 2025

Photocages are protecting groups that can be unmasked with light irradiation and provide spatiotemporal control over the activity of a biomolecule.

Language: Английский

Citations

0

Conceptual expansion of photomedicine for spatiotemporal treatment methods DOI Creative Commons
P. K. Hashim,

Ashwin T Shaji,

Ammathnadu S. Amrutha

et al.

RSC Medicinal Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review covers the history of light therapy, emergence photopharmacology, its methods, and challenges. Current advancements show promise for treating diseases like cancer with precision minimal side effects.

Language: Английский

Citations

0

Exploring the Phototherapeutic Applications of Mitochondria-Targeted COUPY Photocages of Antitumor Drugs DOI

Marta López‐Corrales,

Eduardo Izquierdo‐García, Manel Bosch

et al.

Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: 68(9), P. 9741 - 9754

Published: April 28, 2025

Photocleavable protecting groups hold great promise in photopharmacology to control the release of bioactive molecules from their caged precursors within specific subcellular compartments. Herein, we describe a series photocages based on COUPY scaffold, incorporating chlorambucil (CLB) and 4-phenylbutyric acid (4-PBA) as payloads that can be efficiently activated with visible light. Confocal microscopy confirmed preferential accumulation CLB 4-PBA N-hexyl mitochondria, which exhibited remarkable phototoxicity against cancer cells upon green-yellow light irradiation, IC50 values nanomolar range. This effect was attributed synergistic mechanism involving photorelease intrinsic photogeneration Type I II ROS by scaffold mitochondria. Thus, COUPY-caged derivatives underscore potential COUPY-caging versatile platform develop innovative light-activated agents operating simultaneously through photodynamic therapy photoactivated chemotherapy.

Language: Английский

Citations

0

Innovative Application of Conventional Hydrazone Analogues as Photocages with Ultrahigh Photolysis Efficiency for Dynamic Bioimaging and Prodrug Construction DOI
Hongmei Wu,

Yongxiao Sun,

Yanbing Ke

et al.

Sensors and Actuators B Chemical, Journal Year: 2025, Volume and Issue: unknown, P. 137907 - 137907

Published: May 1, 2025

Language: Английский

Citations

0

Wavelength-Selective Xanthene-Based Monochromophoric Photoremovable Protecting Groups for Tuning Soft Matter Material Properties DOI

Saugat Mondal,

Wai Lean Koay,

Ishan Daga

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(33), P. 23376 - 23386

Published: Aug. 8, 2024

Photocontrolled deprotection of specific functional groups has garnered significant interest over the past two decades. Notably, selective distinct based on wavelength emerged as a prominent focus in recent research. The achievement this objective primarily involved utilization linker-based bichromophoric systems and diverse cocktail mixtures photoresponsive protecting (PRPGs), each responsive to varying wavelengths light. Herein, we present first wavelength-selective monochromophoric system hydroxanthene moiety, enabling release functionalities under 450 600 nm light, respectively. mechanism photodegradation was thoroughly investigated by 1H NMR, UV–vis, fluorescence spectroscopy, suggesting proton-coupled electron transfer photorelease step arylmethyl type second step. utility xanthene-based PRPGs demonstrated multistep degradation microparticles dual-color tuning polymer chain architecture, thus opening an avenue design advanced photoreactive wavelength-controlled for applications soft matter materials.

Language: Английский

Citations

3

Reversible covalent c-Jun N-terminal kinase inhibitors targeting a specific cysteine by precision-guided Michael-acceptor warheads DOI Creative Commons
Dániel Bálint, Ádám Levente Póti, Anita Alexa

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Oct. 4, 2024

Language: Английский

Citations

3

Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells DOI Creative Commons

Marta López‐Corrales,

Anna Rovira,

Albert Gandioso

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7128 - 7140

Published: May 20, 2023

Releasing bioactive molecules in specific subcellular locations from the corresponding caged precursors offers great potential photopharmacology, especially when using biologically compatible visible light. By taking advantage of intrinsic preference COUPY coumarins for mitochondria and their long wavelength absorption region, we have synthesized fully characterized a series COUPY-caged model compounds to investigate how structure coumarin caging group affects rate efficiency photolysis process. Uncaging studies yellow (560 nm) red light (620 phosphate-buffered saline medium demonstrated that incorporation methyl position adjacent photocleavable bond is particularly important fine-tune photochemical properties group. Additionally, use version protonophore 2,4-dinitrophenol allowed us confirm by confocal microscopy photoactivation can occur within living HeLa cells upon irradiation with low doses The new photolabile protecting groups presented here complement toolbox therapeutic applications since they will facilitate delivery photocages active into mitochondria.

Language: Английский

Citations

7

All-photonic kinase inhibitors: light-controlled release-and-report inhibition DOI Creative Commons
Cassandra L. Fleming, Carlos Benitez‐Martin, Elin Bernson

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(18), P. 6897 - 6905

Published: Jan. 1, 2024

An all-photonic method is described, in which (i) the release of an active kinase inhibitor controlled externally with light; and (ii) fluorescence employed to report both binding its corresponding target.

Language: Английский

Citations

2