Pyrrole Hemithioindigo Antimitotics with Near‐Quantitative Bidirectional Photoswitching that Photocontrol Cellular Microtubule Dynamics with Single‐Cell Precision**

Sailer, Alexander; Meiring, Joyce; Heise, Constanze; Pettersson, Linda N.; Akhmanova, Anna; Ahlfeld, Julia; Thorn‐Seshold, Oliver

doi:10.1002/anie.202104794

Cited by 43 publications

(45 citation statements)

References 62 publications

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“…Photoinduced geometry change in a hemithioindigo based molecular motor has been used to modulate catalytic efficiency of a chemical reaction [138] . Pyrrole hemithioindigo 57 has been employed in the photocontrol of cellular microtubule dynamics and cell cycle progression and cell death [139] …”

Section: Different Classes Of Visible Light‐driven Molecular Switches...mentioning

confidence: 99%

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Visible Light‐Driven Molecular Switches and Motors: Recent Developments and Applications

Wang

Bisoyi

Zhang

et al. 2022

Chemistry A European J

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Inspired by human vision, a diverse range of light‐driven molecular switches and motors have been developed for fundamental understanding and application in material science and biology. Recently, the design and synthesis of visible light‐driven molecular switches and motors have been actively pursued. This emerging trend is partly motivated to avoid the harmful effects of ultraviolet light, which was necessary to drive the classical molecular switches and motors at least in one direction, impeding their employment in biomedical and photopharmacology applications. Moreover, visible light‐driven molecular switches and motors are demonstrated to enable benign optical materials for advanced photonic devices. Therefore, during the past several years, visible light‐driven molecular switches based on azobenzene derivatives, diarylethenes, 1,2‐dicyanodithienylethenes, hemithioindigo derivatives, iminothioindoxyls, donor‐acceptor Stenhouse adducts, and overcrowded alkene based molecular motors have been judiciously designed, synthesized, and used in the development of functional materials and systems for a wide range of applications. In this Review, we present the recent developments toward the design of visible light‐driven molecular switches and motors, with their applications in the fabrication of functional materials and systems in material science, bioscience, pharmacology, etc. The visible light‐driven molecular switches and motors realized so far undoubtedly widen the scope of these interesting compounds for technological and biological applications. We hope this Review article could provide additional impetus and inspire further research interests for future exploration of visible light‐driven advanced materials, systems, and devices.

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Section: Different Classes Of Visible Light‐driven Molecular Switches...mentioning

confidence: 99%

“…[138] Pyrrole hemithioindigo 57 has been employed in the photocontrol of cellular microtubule dynamics and cell cycle progression and cell death. [139]…”

Section: Hemithioindigos and Iminothioindoxylsmentioning

confidence: 99%

Visible Light‐Driven Molecular Switches and Motors: Recent Developments and Applications

Wang

Bisoyi

Zhang

et al. 2022

Chemistry A European J

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“…In subsequent studies, Sailer et al implemented near-quantitative photoswitchable pyrrole HPIs to address two additional factors that limit the photoswitchability of azobenzenes in biological assays: the limited bidirectional photoisomerization within the biologically compatible light spectrum and the restricted accessibility of high photostationary states due to fixed-wavelength lasers available in confocal microscopes [ 44 ].…”

Section: Photoswitchable Microtubule-targeting Agentsmentioning

confidence: 99%

“…Remarkably, they also demonstrated that during confocal microscopy this compound can be photoactivated in live cells with spatial and temporal precision. Whereas microtubule dynamics were not significantly influenced by the addition of the Z -isomer, irradiation with 442 nm laser pulses resulted in suppressed microtubule dynamics [ 44 ].…”

Section: Photoswitchable Microtubule-targeting Agentsmentioning

confidence: 99%

Photopharmacology of Antimitotic Agents

Kirchner

Pianowski

2022

IJMS

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Antimitotic agents such as the clinically approved vinca alkaloids, taxanes and epothilone can arrest cell growth during interphase and are therefore among the most important drugs available for treating cancer. These agents suppress microtubule dynamics and thus interfere with intracellular transport, inhibit cell proliferation and promote cell death. Because these drugs target biological processes that are essential to all cells, they face an additional challenge when compared to most other drug classes. General toxicity can limit the applicable dose and therefore reduce therapeutic benefits. Photopharmacology aims to avoid these side-effects by introducing compounds that can be applied globally to cells in their inactive form, then be selectively induced to bioactivity in targeted cells or tissue during a defined time window. This review discusses photoswitchable analogues of antimitotic agents that have been developed by combining different photoswitchable motifs with microtubule-stabilizing or microtubule-destabilizing agents.

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“…These compounds, which are cell-compatible and show antimitotic photoswitchable bioactivity, have been named hemithioindigo-colchicinoid tubulin binders (HOTubs, 450 nm) ( Sailer et al, 2019 ). Likewise, the microtubule inhibitor colchicine served as template for the design of pyrrole hemithioindigo (PHTubs) compounds (photoswitched in the range 435–450 nm) ( Sailer et al, 2021 ). Furthermore, colchicine has been used as structural reference for the development of photoswitchable cytotoxic compounds based on spiropyran (SP, exposed to UV light at 365 nm) ( Rastogi et al, 2021 ).…”

Section: Photopharmacology: Light-triggered Analogues Of Mta Smentioning

confidence: 99%

Recent Approaches to the Identification of Novel Microtubule-Targeting Agents

Eli

Castagna

Mapelli

et al. 2022

Front. Mol. Biosci.

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Microtubules are key components of the eukaryotic cytoskeleton with essential roles in cell division, intercellular transport, cell morphology, motility, and signal transduction. They are composed of protofilaments of heterodimers of α-tubulin and β-tubulin organized as rigid hollow cylinders that can assemble into large and dynamic intracellular structures. Consistent with their involvement in core cellular processes, affecting microtubule assembly results in cytotoxicity and cell death. For these reasons, microtubules are among the most important targets for the therapeutic treatment of several diseases, including cancer. The vast literature related to microtubule stabilizers and destabilizers has been reviewed extensively in recent years. Here we summarize recent experimental and computational approaches for the identification of novel tubulin modulators and delivery strategies. These include orphan small molecules, PROTACs as well as light-sensitive compounds that can be activated with high spatio-temporal accuracy and that represent promising tools for precision-targeted chemotherapy.

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Pyrrole Hemithioindigo Antimitotics with Near‐Quantitative Bidirectional Photoswitching that Photocontrol Cellular Microtubule Dynamics with Single‐Cell Precision**

Cited by 43 publications

References 62 publications

Visible Light‐Driven Molecular Switches and Motors: Recent Developments and Applications

Visible Light‐Driven Molecular Switches and Motors: Recent Developments and Applications

Photopharmacology of Antimitotic Agents

Recent Approaches to the Identification of Novel Microtubule-Targeting Agents

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