Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors
Abstract: The use of light as an external trigger to change ligand shape and as a result its bioactivity, allows the probing of pharmacologically relevant systems with spatiotemporal resolution. A hetero-stilbene lead resulting from the screening of a compound that was originally designed as kinase inhibitor served as a starting point for the design of photoswitchable sirtuin inhibitors. Because the original stilbenoid structure exerted unfavourable photochemical characteristics it was remodelled to its heteroarylic diazeno analogue. By this intramolecular azologization, the shape of the molecule was left unaltered, whereas the photoswitching ability was improved. As anticipated, the highly analogous compound showed similar activity in its thermodynamically stable stretched-out (E)-form. Irradiation of this isomer triggers isomerisation to the long-lived (Z)-configuration with a bent geometry causing a considerably shorter end‐to‐end distance. The resulting affinity shifts are intended to enable real‐time photomodulation of sirtuins in vitro
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Anmerkungen
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Beilstein journal of organic chemistry. - 15 (2019) , 2170-2183, ISSN: 1860-5397
- Ereignis
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Veröffentlichung
- (wo)
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Freiburg
- (wer)
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Universität
- (wann)
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2020
- Urheber
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Grathwol, Christoph Werner
Wössner, Natalie
Swyter, Sören
Smith, Adam C.
Tapavicza, Enrico
Hofstetter, Robert K.
Bodtke, Anja
Jung, Manfred
Link, Andreas
- Beteiligte Personen und Organisationen
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Pharmazeutische und Medizinische Chemie, Arbeitskreis Manfred Jung
- DOI
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10.3762/bjoc.15.214
- URN
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urn:nbn:de:bsz:25-freidok-1540684
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:21 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Grathwol, Christoph Werner
- Wössner, Natalie
- Swyter, Sören
- Smith, Adam C.
- Tapavicza, Enrico
- Hofstetter, Robert K.
- Bodtke, Anja
- Jung, Manfred
- Link, Andreas
- Pharmazeutische und Medizinische Chemie, Arbeitskreis Manfred Jung
- Universität
Entstanden
- 2020
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