Visible light initiated release of calcium ions through photochemical electron transfer reactions

Heymann, Romina R.; Thum, Matthew D.; Hardee, Apryl L.; Falvey, Daniel E.

doi:10.1039/c6pp00469e

Cited by 7 publications

(8 citation statements)

References 34 publications

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“…In another case, these authors demonstrated the efficient release of calcium ions (Ca 2+ ) from an EDTA complex facilitated by photolysis of riboflavin photocatalysts at λ irr > 440 nm. 1410 An interesting visible-light uncaging reaction using photocatalytic deboronative hydroxylation was recently reported by Chen and co-workers (one example is presented in Scheme 92. 1411 Phenol, alcohol, and amine derivatives were liberated from the corresponding boronates in high chemical yields in bacteria and mammalian cells by reaction with transient hydrogen peroxides generated in the presence of molecular oxygen using fluorescein or rhodamine derivatives as photocatalysts and ascorbate as a reductant.…”

Section: Photosensitized Release: From Small Molecules To Nanoparticl...mentioning

confidence: 97%

“…The authors proposed photodeprotection mechanisms involving both oxidative and reductive quenching scenarios (Scheme ) corresponding to the general mechanism shown in Scheme d. In another case, these authors demonstrated the efficient release of calcium ions (Ca 2+ ) from an EDTA complex facilitated by photolysis of riboflavin photocatalysts at λ irr > 440 nm …”

Section: Photosensitized Release: From Small Molecules To Nanoparticl...mentioning

confidence: 99%

“… This species has a large two-photon cross section (350 GM) at 775 nm. Ca 2+ photorelease (/uptake) has also been accomplished using a photoswitchable diarylethene-containing chelator, visible-light irradiation of flavin photosensitizers in the presence of Ca 2+ -EDTA, and two-photon excitation of a 5-bromo-2-nitrobenzyl-substituted ethylene glycol tetraacetic acid chelator . The last example discussed here is a system that releases metal ions such as Ca 2+ or Zn 2+ from polymersomes, that is, bilayer vesicles that self-assemble from amphiphilic diblock copolymers .…”

Section: Release Mediated By Photoswitchingmentioning

confidence: 99%

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Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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Photoactivatable (alternatively, photoremovable, photoreleasable, or photocleavable) protecting groups (PPGs), also known as caged or photocaged compounds, are used to enable non-invasive spatiotemporal photochemical control over the release of species of interest. Recent years have seen the development of PPGs activatable by biologically and chemically benign visible and near-infrared (NIR) light. These long-wavelength-absorbing moieties expand the applicability of this powerful method and its accessibility to non-specialist users. This review comprehensively covers organic and transition metal-containing photoactivatable compounds (complexes) that absorb in the visible- and NIR-range to release various leaving groups and gasotransmitters (carbon monoxide, nitric oxide, and hydrogen sulfide). The text also covers visible- and NIR-light-induced photosensitized release using molecular sensitizers, quantum dots, and upconversion and second-harmonic nanoparticles, as well as release via photodynamic (photooxygenation by singlet oxygen) and photothermal effects. Release from photoactivatable polymers, micelles, vesicles, and photoswitches, along with the related emerging field of photopharmacology, is discussed at the end of the review.

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Section: Photosensitized Release: From Small Molecules To Nanoparticl...mentioning

confidence: 97%

Section: Photosensitized Release: From Small Molecules To Nanoparticl...mentioning

confidence: 99%

Section: Release Mediated By Photoswitchingmentioning

confidence: 99%

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Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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“…4The rate of Ca 2+ release is >20 times faster than those for riboflavin and enzyme catalysts, UV irradiation, and diffusion from a CaSO 4 slurry ( Supplementary Fig. 11) 19,[33][34][35] . These advantages facilitate the rapid, large-scale fabrication of hydrogels, which is highly desirable for industrial applications.…”

Section: Resultsmentioning

confidence: 99%

Visible-light-assisted multimechanism design for one-step engineering tough hydrogels in seconds

et al. 2020

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Tough hydrogels that are capable of efficient mechanical energy dissipation and withstanding large strains have potential applications in diverse areas. However, most reported fabrication strategies are performed in multiple steps with long-time UV irradiation or heating at high temperatures, limiting their biological and industrial applications. Hydrogels formed with a single pair of mechanisms are unstable in harsh conditions. Here we report a one-step, biocompatible, straightforward and general strategy to prepare tough soft hydrogels in a few tens of seconds under mild conditions. With a multimechanism design, the network structures remarkably improve the mechanical properties of hydrogels and maintain their high toughness in various environments. The broad compatibility of the proposed method with a spectrum of printing technologies makes it suitable for potential applications requiring high-resolution patterns/structures. This strategy opens horizons to inspire the design and application of high-performance hydrogels in fields of material chemistry, tissue engineering, and flexible electronics.

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“…Photoreleased molecules are of considerable interest not only in the field of photochemistry but also in site‐specific delivery applications . Current literature on sensitizer and drug photorelease has mainly focused on the use of direct UV, visible and near‐IR light to activate the release mechanisms.…”

Section: Introductionmentioning

confidence: 99%

S,S‐Chiral Linker Induced U Shape with a Syn‐facial Sensitizer and Photocleavable Ethene Group

Ghosh

Belh

Chiemezie

et al. 2018

Photochem & Photobiology

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There is a major need for light-activated materials for the release of sensitizers and drugs. Considering the success of chiral columns for the separation of enantiomer drugs, we synthesized an S,S-chiral linker system covalently attached to silica with a sensitizer ethene near the silica surface. First, the silica surface was modified to be aromatic rich, by replacing 70% of the surface groups with (3-phenoxypropyl)silane. We then synthesized a 3-component conjugate [chlorin sensitizer, S,S-chiral cyclohexane and ethene building blocks] in 5 steps with a 13% yield, and covalently bound the conjugate to the (3-phenoxypropyl)silane-coated silica surface. We hypothesized that the chiral linker would increase exposure of the ethene site for enhanced O -based sensitizer release. However, the chiral linker caused the sensitizer conjugate to adopt a U shape due to favored 1,2-diaxial substituent orientation; resulting in a reduced efficiency of surface loading. Further accentuating the U shape was π-π stacking between the (3-phenoxypropyl)silane and sensitizer. Semiempirical calculations and singlet oxygen luminescence data provided deeper insight into the sensitizer's orientation and release. This study has lead to insight on modifications of surfaces for drug photorelease and can help lead to the development of miniaturized photodynamic devices.

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Visible light initiated release of calcium ions through photochemical electron transfer reactions

Cited by 7 publications

References 34 publications

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Visible-light-assisted multimechanism design for one-step engineering tough hydrogels in seconds

S,S‐Chiral Linker Induced U Shape with a Syn‐facial Sensitizer and Photocleavable Ethene Group

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