Azobenzenes: The Quest for Visible Light Triggering

Koch, Vanessa; Bräse, Stefan

doi:10.1002/9783527827626.ch3

Cited by 4 publications

(3 citation statements)

References 87 publications

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“…An alternative strategy involves conferring photosensitivity upon bioactive small molecules. [2] This is frequently achieved by introducing or substituting specific components of their structure with molecular photoswitches [3] -substances that exhibit reversible alterations in properties (such as shape and polarity) upon exposure to light, with azobenzene derivatives [4] being the most commonly used. This emerging approach known as "photopharmacology" [5] has given rise to a plethora of compounds with potential antimicrobial [6] and anticancer applications.…”

Section: Introductionmentioning

confidence: 99%

Reversible Influence of Hemipiperazine Photochromism on the Early Development of Zebrafish Embryo

Seliwjorstow,

Takamiya,

Rastegar

et al. 2024

ChemBioChem

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This study explores the potential of controlling organismal development with light by using reversible photomodulation of activity in bioactive compounds. Specifically, our research focuses on plinabulin 1, an inhibitor of tubulin dynamics that contains a photochromic motif called hemipiperazine. The two isomeric forms, Z‐1 and E‐1, can partially interconvert with light, yet show remarkable thermal stability in darkness. The Z‐isomer exhibits higher cytotoxicity due to stronger binding to α‐tubulin's colchicine site. The less toxic E‐1 form, considered a "pro‐drug", can be isolated in vitro and stored. Upon activation by blue or cyan light, it predominantly generates the more toxic Z‐1 form. Here we demonstrate that 1 can effectively photomodulate epiboly, a critical microtubule‐dependent cell movement during gastrulation in zebrafish embryos. This research highlights the potential of photomodulation for precise and reversible control of cellular activities and organismal development.

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Section: Introductionmentioning

confidence: 99%

Reversible Influence of Hemipiperazine Photochromism on the Early Development of Zebrafish Embryo

Seliwjorstow,

Takamiya,

Rastegar

et al. 2024

ChemBioChem

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“…For trans -azobenzene, there is a π→π* band around 320 nm and a very weak (symmetry-forbidden) n→π* band around 440 nm. cis -Azobenzene shows two bands at 240 and 280 nm, and the n→π* transition is slightly more allowed than for trans -azobenzene [ 15 ]. As the bands of cis - and trans -azobenzene overlap, irradiation results in a photostationary state (PSS) which is a mixture of the isomers.…”

Section: Introductionmentioning

confidence: 99%

A fiber-optic spectroscopic setup for isomerization quantum yield determination

Volker,

Steen,

Crespi

2024

Beilstein J. Org. Chem.

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A spectroscopic setup for isomerization quantum yield determination is reported. The setup combines fiber-coupled LEDs, a commercially calibrated thermopile detector for measurement of the photon flux, and a fiber-coupled UV–vis spectrometer. By solving the rate equations numerically, isomerization quantum yields can be obtained from the UV–vis absorption spectra. We show that our results for the prototypical photoswitch azobenzene are in excellent agreement with the literature. The analysis of the errors showed that the quantum yields determined using this method are in the same order of magnitude as when using actinometry, thus demonstrating the reliability of our setup.

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“…Small photoswitchable compounds have recently garnered significant attention due to their wide range of applications in fields such as materials sciences, [1] supramolecular chemistry, [2] catalysis, [3] and biology [4] . These molecules undergo reversible structural changes upon irradiation with light and can be classified into various classes, including azobenzenes, [5] stilbenes, [6] spiropyrans [7] or dithienylethenes [8] . To distinguish themselves from these structures, which have been explored over decades, a few research groups have recently focused on developing hemithioindigos (HTIs) as emerging photoswitches [9] .…”

Section: Introductionmentioning

confidence: 99%

Easily Accessible Substituted Heterocyclic Hemithioindigos as Bistable Molecular Photoswitches

Gernet,

El Rhaz,

Jean

2023

Chemistry A European J

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Thioaurone chromophores, part of the indigoid family and commonly named hemithioindigos, have recently gained attention due to their interesting photoswitching properties. The study focuses on heterocyclic hemithioindigos (Het-HTIs) and investigates their synthesis using electron-rich and electron-poor heterocycles and modifications to the thioindigo moiety. Furthermore, it aims to evaluate the photoswitching performances of these synthesised compounds, with a particular emphasis on the influence of the heterocycles on the photoisomerization capabilities, which was found to be more prominent than the modifications made to the thioindigo moiety. Among the 44 Het-HTIs tested, several exhibited highly efficient photoswitchable properties, demonstrating Z-to-E photoisomerization in the blue region, and E-to-Z photoisomerization in the green or the red regions. Additionally, the metastable E-isomer displayed an impressive half-life of up to 54 days in a polar solvent (DMSO). These results suggest that heterocyclic hemithioindigos hold great promise as photoswitches for researchers interested in light-controlled molecular mechanisms.

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Azobenzenes: The Quest for Visible Light Triggering

Cited by 4 publications

References 87 publications

Reversible Influence of Hemipiperazine Photochromism on the Early Development of Zebrafish Embryo

Reversible Influence of Hemipiperazine Photochromism on the Early Development of Zebrafish Embryo

A fiber-optic spectroscopic setup for isomerization quantum yield determination

Easily Accessible Substituted Heterocyclic Hemithioindigos as Bistable Molecular Photoswitches

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