Photoswitchable Electrical Communication of Glucose Oxidase and Glutathione Reductase with Electrode Surfaces through Photoisomerizable Redox Mediators

Lion‐Dagan, Mazzi; Marx–Tibbon, Sharon; Katz, Eugenii; Willner, Itamar

doi:10.1002/anie.199516041

Cited by 44 publications

(25 citation statements)

References 13 publications

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“…During purification, some cleavage of the silyl groups occurs, but the deprotected amine 3 can be collected. 1 4-Aminophenyldiphenyl methanol (4). Crude 3 (ϳ27 mmol) was placed in a flask equipped with a stirbar, nitrogen inlet and reflux condenser.…”

Section: Methodsmentioning

confidence: 99%

“…Melting point: 180-182ЊC. 1 Chemical actinometry. From the point of view of actinometry, it is best to have the source wavelength range smaller than the absorption wavelength range of the dye.…”

Section: -[Bis(ethoxycarbonylmethyl-amino)-phenyl] Diphenyl Methanolmentioning

confidence: 99%

“…Photochromic compounds have been used to control protein and enzyme activity (1–12) and metal‐ion binding (13–31). In metal‐ion binding systems, light can be used to drive photochromic molecules from one stable or metastable avid binding structure to another stable or metastable loosely binding structure.…”

Section: Introductionmentioning

confidence: 99%

“…Photochromic compounds have been used to control protein and enzyme activity (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) and metal-ion binding (13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31). In metal-ion binding systems, light can be used to drive photochromic molecules from one stable or metastable avid binding structure to another stable or metastable loosely binding struc- ¶Posted on the website on December 31,2001.…”

Section: Introductionmentioning

confidence: 99%

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Kinetic Analysis of a Photosensitive Chelator and its Complex with Zn(II)¶

Stephens

Geary

Weber

2007

Photochemistry and Photobiology

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The reversible sequestration and release of metal ions is an important objective in biological and environmental research. Unfortunately, although there have been dramatic examples of metal ion activity control, there are very few quantitative investigations of stoichiometry, equilibria and kinetics. A significant contributor to this lack of quantitative work is the complexity of many photochromic systems. Therefore, we have attempted to create a simple, reversible photochromic metal‐ion chelator that can be analyzed quantitatively. The chelator should have certain other attributes as well, namely, that it binds to divalent metal ions (because of their extreme biological importance) and that it binds metal ions in the dark so that light is used to release metal ions rather than sequester them. The photochromic chelator (1) binds to divalent metal ions [Zn(II), Cu(II), Pb(II), Hg(II), Fe(II), Co(II) and Cd(II); other metal ions have not yet been tested] in the dark with a significant binding strength. In both methanol (by spectrophotometry) and methanol–water (by voltammetry), the stoichiometry of the 1–Zn(II) complex is 2:1. The binding constant (K1K2) is on the order of 1012–1014M−2 in methanol and 5.0 × 108M−2 in 50% aqueous methanol. The chelator 1 is photolabile, yielding 2 with a quantum efficiency of 0.91. In a solution containing excess Zn(II), so that over 99% of the ligand exists as the monodentate complex, photolysis produces 2 with a quantum efficiency of 0.15. A kinetic analysis leads to the conclusion that the complex itself is photolabile.

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Section: Methodsmentioning

confidence: 99%

Section: -[Bis(ethoxycarbonylmethyl-amino)-phenyl] Diphenyl Methanolmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Kinetic Analysis of a Photosensitive Chelator and its Complex with Zn(II)¶

Stephens

Geary

Weber

2007

Photochemistry and Photobiology

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“…Figure C shows the reversible change of the bioelectrocatalytic reaction rate obtained by cyclic Vis‐UV irradiation. Similar results have been received with another photoswitchable mediator (ferrocene derivative) communicating with immobilized GOx, thus demonstrating a general concept of the enzyme switchable operation controlled by the photoisomerizable electron transfer mediators .…”

Section: Spiropyran‐merocyanine‐based Photoelectrochemical Switchesmentioning

confidence: 99%

Modified Electrodes and Electrochemical Systems Switchable by Light Signals

Katz¹

2018

Electroanalysis

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This article is an overview of extensive research efforts in many laboratories in the last two decades in the area of light‐switchable electrochemical systems and modified electrodes. Electrochemical reactions, including electrocatalytic and bioelectrocatalytic processes, have been reversibly activated and inhibited upon irradiation with light at different wavelengths. In order to realize these light activated or inhibited processes, the electrodes or/and reacting molecules were functionalized with photoisomerizable molecules including various derivatives of diarylethene, phenoxynaphthacenequinone, azobenzene and spiropyran/merocyanine. Photochemical reactions of these species resulted in change of their redox activity, conformation and electrical charge. All these changes affected electrode surfaces or (bio)molecules resulting in switching ON‐OFF corresponding (bio)electrochemical processes. Various systems based on different light‐controlled reactions are reviewed and discussed with specific examples and with many illustrating figures. Possible extensions of the research area and future applications are briefly overviewed in the conclusion section. The present comprehensive review is addressed to a broad scientific community, including newcomers to the area.

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Gated molecular and biomolecular optoelectronic systems via photoisomerizable monolayer electrodes

Willner

Doron

Katz

1998

J. Phys. Org. Chem.

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Reversible electronic transduction of photonic processes occurring on electrodes is the conceptual method to develop molecular and biomolecular optoelectronic systems. Cyclic photochemical activation of molecular or biomolecular monolayer redox-functions provides a general methodology for the amperometric transduction of photonic information that is recorded by the chemical assembly. Alternatively, photoisomerizable monolayers associated with electrodes act as "command interfaces" for controlling the interfacial electron transfer between molecular redox-species or redox-proteins. The systems use a photonic input for the generation of an electronic output and act as information processing assemblies. Programmed arrays of photosensitizer/electron acceptor cross-linked Au-nanoparticle arrays are assembled on indium tin oxide (ITO) for photoelectrochemical applications.

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Photoswitchable Electrical Communication of Glucose Oxidase and Glutathione Reductase with Electrode Surfaces through Photoisomerizable Redox Mediators

Cited by 44 publications

References 13 publications

Kinetic Analysis of a Photosensitive Chelator and its Complex with Zn(II)¶

Kinetic Analysis of a Photosensitive Chelator and its Complex with Zn(II)¶

Modified Electrodes and Electrochemical Systems Switchable by Light Signals

Gated molecular and biomolecular optoelectronic systems via photoisomerizable monolayer electrodes

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