Covalent and Visible‐Light Photoswitchable Derivatives of the Potent Synthetic Opioid Isotonitazene and Other Nitazenes
Abstract: Isotonitazene belongs to a potent class of μ‐opioid receptor (μOR) ligands, known as nitazenes. The lack of knowledge surrounding this agonist and others in its class has sparked thorough re‐investigations. To aid in these investigations, the purportedly covalent yet underexplored nitazene BIT was biochemically re‐evaluated in this work, along with a newly synthesized analogue, Iso‐BIT. Moreover, in the pursuit of understanding the mechanism, function and interactions of the μOR, this study involved developing photoswitchable nitazene derivatives as potential probe molecules. Converting known ligands into azo‐containing photoswitchable derivatives offers the opportunity to modulate ligand structure with light, allowing for photocontrol of compound activity. While photocontrol of μOR activity could not be entirely achieved, photophysical evaluation of these 2‐benzimidazole azo‐arenes revealed a novel photoswitch scaffold that responds to visible light. Furthermore, azo‐containing 2 e and 3 e emerged as promising nitazene derivatives that were able to form an exceptionally high fraction of covalent‐ligand receptor complexes with wild‐type μOR at physiological pH.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Covalent and Visible‐Light Photoswitchable Derivatives of the Potent Synthetic Opioid Isotonitazene and Other Nitazenes ; day:10 ; month:06 ; year:2024 ; extent:12
ChemPhotoChem ; (10.06.2024) (gesamt 12)
- Creator
- DOI
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10.1002/cptc.202400022
- URN
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urn:nbn:de:101:1-2406101416396.665643165876
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:55 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Lahmy, Ranit
- Hübner, Harald
- Gmeiner, Peter
- König, Burkhard
Other Objects (12)
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Covalent and Visible‐Light Photoswitchable Derivatives of the Potent Synthetic Opioid Isotonitazene and Other Nitazenes
Synthesis of covalent and non-covalent photoswitchable derivatives and their biological applications
Synthesis and Characterization of Photoswitchable Covalent Ligands for the beta2 - Adrenoceptor
Visible‐Light Photoswitchable Benzimidazole Azo‐Arenes as β‐Arrestin2‐Biased Selective Cannabinoid 2 Receptor Agonists
Development of Photoswitchable Tethered Ligands that Target the μ‐Opioid Receptor
Tailor‐Made Photoconductive Pyrene‐Based Covalent Organic Frameworks for Visible‐Light Driven Hydrogen Generation
Dynamic Covalent Chemistry for Accelerated Photoswitch Discovery and Photoswitchable Core-Shell Metal-Organic Frameworks
Covalent Triazine Framework Nanoparticles via Size‐Controllable Confinement Synthesis for Enhanced Visible‐Light Photoredox Catalysis
Introducing a photo-switchable azo-functionality inside Cr-MIL-101-NH2 by covalent post-synthetic modification
Covalent Polymer‐RNA Conjugates for Potent Activation of the RIG‐I Pathway
Photoswitchable and non-photoswitchable tubulin inhibitors for applications in cell biology
Photoswitchable monolayers on silicon
Covalent and Visible‐Light Photoswitchable Derivatives of the Potent Synthetic Opioid Isotonitazene and Other Nitazenes
Synthesis of covalent and non-covalent photoswitchable derivatives and their biological applications
Synthesis and Characterization of Photoswitchable Covalent Ligands for the beta2 - Adrenoceptor
Visible‐Light Photoswitchable Benzimidazole Azo‐Arenes as β‐Arrestin2‐Biased Selective Cannabinoid 2 Receptor Agonists
Development of Photoswitchable Tethered Ligands that Target the μ‐Opioid Receptor
Tailor‐Made Photoconductive Pyrene‐Based Covalent Organic Frameworks for Visible‐Light Driven Hydrogen Generation
Dynamic Covalent Chemistry for Accelerated Photoswitch Discovery and Photoswitchable Core-Shell Metal-Organic Frameworks
Covalent Triazine Framework Nanoparticles via Size‐Controllable Confinement Synthesis for Enhanced Visible‐Light Photoredox Catalysis
Introducing a photo-switchable azo-functionality inside Cr-MIL-101-NH2 by covalent post-synthetic modification
Covalent Polymer‐RNA Conjugates for Potent Activation of the RIG‐I Pathway
Photoswitchable and non-photoswitchable tubulin inhibitors for applications in cell biology