Photoisomerization of hemithioindigo compounds: Combining solvent- and substituent- effects into an advanced reaction model

Graupner, Franziska F.; Herzog, Teja T.; Rott, Florian; Oesterling, Sven; Vivie‐Riedle, Regina de; Cordes, Thorben

doi:10.1016/j.chemphys.2018.07.043

Cited by 16 publications

(16 citation statements)

References 28 publications

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“…257 HTIs show very fast E-Z photoisomerization kinetics as single compounds or when attached to macromolecules 244,248 and the isomerization mechanism, solvent and substituent effects were studied in detail. 258 Decoration with suitable substituents can accelerate the light-induced isomerization even more. When the thioindigo fragment is used as acceptor and the stilbene fragment, functionalized with electron-donating substituents in ortho and para-position, is used as a donor moiety, the photoisomerization occurs in the low ps-range.…”

Section: Photoswitches Relying On the Isomerization About Double-bondsmentioning

confidence: 99%

Molecular photoswitches in aqueous environments

et al. 2021

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Section: Photoswitches Relying On the Isomerization About Double-bondsmentioning

confidence: 99%

Molecular photoswitches in aqueous environments

et al. 2021

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“…Recently, the development of photoPROTACs has been the focus of several researchers and has been receiving increasing interest ( Graupner et al, 2018 ; Heindl and Wegner, 2020 ; Pugachev et al, 2020 ). After retrieval of comprehensive information, we found that photochromic and photocleavable functional groups are most extensively used in photoPROTAC development.…”

Section: Progress Of Photoprotac Developmentmentioning

confidence: 99%

Photopharmacology of Proteolysis-Targeting Chimeras: A New Frontier for Drug Discovery

et al. 2021

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Photopharmacology is an emerging field that uses light to precisely control drug activity. This strategy promises to improve drug specificity for reducing off-target effects. Proteolysis-targeting chimeras (PROTACs) are an advanced technology engineered to degrade pathogenic proteins through the ubiquitin-proteasome system for disease treatment. This approach has the potential to target the undruggable proteome via event-driven pharmacology. Recently, the combination strategy of photopharmacology and PROTACs has gained tremendous momentum for its use in the discovery and development of new therapies. This review systematically focuses on PROTAC-based photopharmacology. Herein, we provide an overview of the new and vibrant research on photoPROTACs, discuss the advantages and disadvantages of this approach as a biological tool, and outline the challenges it faces in a clinical setting.

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“…To date a variety of molecular motors are available, powered by different energy sources, ,− performing different kinds of directional motions, ,− and operating by distinct mechanisms. We have contributed to these developments with visible light responsive molecular motors that are based on the hemithioindigo (HTI) chromophore − and undergo directional rotational motions. − Most recently we presented a molecular motor able to deliver a fully directional eight-shaped motion upon green light irradiation . The next frontier of research is presently headed toward application of molecular motors and integration of their functions with other molecular components.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Relay-Control of Organocatalysis with a Hemithioindigo-Based Molecular Motor

Grill

Dube

2020

J. Am. Chem. Soc.

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Integration of individual molecular components such as molecular motors or switches into larger meta-functional systems represents a current challenge at the forefront of molecular machine research. Here we present a modular supramolecular approach to relay the photoinduced geometry changes of a hemithioindigo based molecular motor into catalytic efficiency of a chemical reaction. Using the intrinsic chemical nature of the motor for recognition of different hydrogenbonding organocatalysts a greater than 10-fold modulation in binding affinity is achieved upon photoisomerization. This change in affinity is then translated effectively into control of catalytic competence of the organocatalysts without direct interference by the motor. As an example the organocatalysed Michael addition reaction between nitrostyrene and 3-methoxy-dimethyl aniline was modulated in situ by visible light irradiation. Thus, dynamic and reversible remote control of catalytic processes by the switching capacity of a hemithioindigo molecular motor is established in a multicomponent chemical system. The high intrinsic modularity of this approach presents further advantages, e.g., for easy tailoring of conditions or facile exchange of catalysts and reactions. These results represent a first stepping stone into integrated chemical networks regulated by molecular machines in a fully dynamic way.

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Photoisomerization of hemithioindigo compounds: Combining solvent- and substituent- effects into an advanced reaction model

Cited by 16 publications

References 28 publications

Molecular photoswitches in aqueous environments

Molecular photoswitches in aqueous environments

Photopharmacology of Proteolysis-Targeting Chimeras: A New Frontier for Drug Discovery

Supramolecular Relay-Control of Organocatalysis with a Hemithioindigo-Based Molecular Motor

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