Transition-Metal-Free CO-Releasing BODIPY Derivatives Activatable by Visible to NIR Light as Promising Bioactive Molecules

Palao, Eduardo; Slanina, Tomáš; Muchová, Lucie; Šolomek, Tomáš; Vı́tek, Libor; Klán, Petr

doi:10.1021/jacs.5b10800

Cited by 273 publications

(282 citation statements)

References 68 publications

(118 reference statements)

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“…These carbon monoxide-releasing molecules were formed from transition-metal-free photolabile constructs based on BODIPY chromophores (COR-BDPs) and were described as a novel visible/NIR (up to 730 nm)-activatable nanosystem. 71 In other applications, photocages have also been suggested for overcoming problems with photoisomerization and enhancing control of the protection/deprotection of thiol groups, e.g., using NDBF photocages. 35 Photocage-based systems can provide advantages such as biocompatible chromophores and red-shifted absorption; 55 two-photon cages can be designed to have enhanced two-photon absorption cross-sections, good water solubility, and low toxicity.…”

Section: Other Applications Of Light In Ddssmentioning

confidence: 99%

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

et al. 2017

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Nanotechnology has begun to play a remarkable role in various fields of science and technology. In biomedical applications, nanoparticles have opened new horizons, especially for biosensing, targeted delivery of therapeutics, and so forth. Among drug delivery systems (DDSs), smart nanocarriers that respond to specific stimuli in their environment represent a growing field. Nanoplatforms that can be activated by an external application of light can be used for a wide variety of photoactivated therapies, especially light-triggered DDSs, relying on photoisomerization, photo-cross-linking/un-cross-linking, photoreduction, and so forth. In addition, light activation has potential in photodynamic therapy, photothermal therapy, radiotherapy, protected delivery of bioactive moieties, anticancer drug delivery systems, and theranostics (i.e., real-time monitoring and tracking combined with a therapeutic action to different diseases sites and organs). Combinations of these approaches can lead to enhanced and synergistic therapies, employing light as a trigger or for activation. Nonlinear light absorption mechanisms such as two-photon absorption and photon upconversion have been employed in the design of light-responsive DDSs. The integration of a light stimulus into dual/multiresponsive nanocarriers can provide spatiotemporal controlled delivery and release of therapeutic agents, targeted and controlled nanosystems, combined delivery of two or more agents, their on-demand release under specific conditions, and so forth. Overall, light-activated nanomedicines and DDSs are expected to provide more effective therapies against serious diseases such as cancers, inflammation, infections, and cardiovascular disease with reduced side effects and will open new doors toward the treatment of patients worldwide.

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Section: Other Applications Of Light In Ddssmentioning

confidence: 99%

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

et al. 2017

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“…17 While two-photon methods provide high spatial resolution, 18 their very small focal volumes currently limit many practical applications. Recently, near-IR photodecaging strategies have been described based on cyanine 19, BODIPY, 20 and phthalocyanine 21 dyes. 22 A current challenge for red- and near-IR photodecaging strategies lies is the need to improve the kinetics of photorelease.…”

Section: Introductionmentioning

confidence: 99%

Rapid Bioorthogonal Chemistry Turn-on through Enzymatic or Long Wavelength Photocatalytic Activation of Tetrazine Ligation

et al. 2016

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Rapid bioorthogonal reactivity can be induced by controllable, catalytic stimuli using air as the oxidant. Methylene blue (4 μM) irradiated with red light (660 nm) catalyzes the rapid oxidation of a dihydrotetrazine to a tetrazine thereby turning on reactivity toward trans-cyclooctene dienophiles. Alternately, the aerial oxidation of dihydrotetrazines can be efficiently catalyzed by nanomolar levels of horseradish peroxidase under peroxide-free conditions. Selection of dihydrotetrazine/tetrazine pairs of sufficient kinetic stability in aerobic aqueous solutions is key to the success of these approaches. In this work, polymer fibers carrying latent dihydrotetrazines were catalytically activated and covalently modified by trans-cyclooctene conjugates of small molecules, peptides and proteins. In addition to visualization with fluorophores, fibers conjugated to a cell adhesive peptide exhibited a dramatically increased ability to mediate contact guidance of cells.

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“…One appealing alternative is to use near-infrared light to deliver bioactive molecules, thereby generating a spatially targeted biological effect while avoiding the undesired side effects associated with systemic delivery. Progress using metallic nanoparticles, liposomal formulations, and, recently, small molecule uncaging has been achieved4567891011121314. However, the site-specific release of bioactive molecules alone sacrifices the benefits of conventional PDT treatments (that is, catalytic light-driven generation of toxic ROS).…”

mentioning

confidence: 99%

Near-infrared uncaging or photosensitizing dictated by oxygen tension

2016

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Existing strategies that use tissue-penetrant near-infrared light for the targeted treatment of cancer typically rely on the local generation of reactive oxygen species. This approach can be impeded by hypoxia, which frequently occurs in tumour microenvironments. Here we demonstrate that axially unsymmetrical silicon phthalocyanines uncage small molecules preferentially in a low-oxygen environment, while efficiently generating reactive oxygen species in normoxic conditions. Mechanistic studies of the uncaging reaction implicate a photoredox pathway involving photoinduced electron transfer to generate a key radical anion intermediate. Cellular studies demonstrate that the biological mechanism of action is O2-dependent, with reactive oxygen species-mediated phototoxicity in normoxic conditions and small molecule uncaging in hypoxia. These studies provide a near-infrared light-targeted treatment strategy with the potential to address the complex tumour landscape through two distinct mechanisms that vary in response to the local O2 environment.

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Transition-Metal-Free CO-Releasing BODIPY Derivatives Activatable by Visible to NIR Light as Promising Bioactive Molecules

Cited by 273 publications

References 68 publications

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

Rapid Bioorthogonal Chemistry Turn-on through Enzymatic or Long Wavelength Photocatalytic Activation of Tetrazine Ligation

Near-infrared uncaging or photosensitizing dictated by oxygen tension

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