ArticleNature chemistry2023
Isomerization of bioactive acylhydrazones triggered by light or thiols.
Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 32 citations in OpenAlex.
- Multiscale Free-Energy Methods for Protonation-Coupled Light-Responsive Binding of Ionizable Photoswitchable eDHFR Inhibitors.Journal of chemical information and modeling · 2026Article
- Dynamic Control of Nucleic Acids Self-Assembly and Expression Using Photoswitches.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Design, Properties and Applications of Multiple Dynamic Hydrogels.Materials (Basel, Switzerland) · 2026Review
- Multistate photoswitches beyond on and off.Nature communications · 2026Review
- Optical control of the cardiac rhythm with photoswitchable NaNature communications · 2026Article
- Novel Antifungal Scaffold Targeting Tubulin Overcomes Sclerotinia Sclerotiorum Resistance.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Hydrazone-based photocages for precise sub-organelle visualization and drug release.Communications chemistry · 2025Article
- An intrinsic self-healable supramolecular dynamic covalent elastomer for sustainable high-performance tactile sensing.Chemical science · 2025Article
- Discovery of novel positive allosteric modulators targeting GluN1/2A NMDARs as anti-stroke therapeutic agents.RSC medicinal chemistry · 2024Article
- Fully Reversible and Super-Fast Photo-Induced Morphological Transformation of Nanofilms for High-Performance UV Detection and Light-Driven Actuators.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
Corrections and comments
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Authors and funding
14 authors at 5 institutions in 2 countries.
Funding
Abstract
The acylhydrazone unit is well represented in screening databases used to find ligands for biological targets, and numerous bioactive acylhydrazones have been reported. However, potential E/Z isomerization of the C=N bond in these compounds is rarely examined when bioactivity is assayed. Here we analysed two ortho-hydroxylated acylhydrazones discovered in a virtual drug screen for modulators of N-methyl-D-aspartate receptors and other bioactive hydroxylated acylhydrazones with structurally defined targets reported in the Protein Data Bank. We found that ionized forms of these compounds, which are populated under laboratory conditions, photoisomerize readily and the isomeric forms have markedly different bioactivity. Furthermore, we show that glutathione, a tripeptide involved with cellular redox balance, catalyses dynamic E⇄Z isomerization of acylhydrazones. The ratio of E to Z isomers in cells is determined by the relative stabilities of the isomers regardless of which isomer was applied. We conclude that E/Z isomerization may be a common feature of the bioactivity observed with acylhydrazones and should be routinely analysed.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.