Rhodanine-Based Chromophores: Fast Access to Capable Photoswitches and Application in Light-Induced Apoptosis Autoren
Köttner L, Wolff F, Mayer P, Zanin E, Dube H (2024)
Publication Language: English
Publication Type: Journal article, Original article
Publication year: 2024
Journal
Book Volume: 146
Pages Range: 1894–1903
Journal Issue: 3
URI: https://pubs.acs.org/doi/abs/10.1021/jacs.3c07710
DOI: 10.1021/jacs.3c07710
Abstract
Molecular photoswitches are highly desirable in all chemistry-related areas of research. They provide effective outside control over geometric and electronic changes at the nanoscale using an easy to apply, waste-free stimulus. However, simple and effective access to such molecular tools is typically not granted, and elaborate syntheses and substitution schemes are needed in order to obtain efficient photoswitching properties. Here we present a series of rhodanine-based photoswitches that can be prepared in one simple synthetic step without requiring elaborate purification. Photoswitching is induced by UV and visible light in both switching directions, and thermal stabilities of the metastable states as well as quantum yields are very high. An additional benefit is the hydrogen-bonding capacity of the rhodanine fragment, which enables applications in supramolecular or medicinal chemistry. We further show that the known rhodanine-based inhibitor SMI-16a is a photoswitchable apoptosis inducer. The biological activity of SMI-16a can effectively be switched ON or OFF by reversible photoisomerization between the inactive E and the active Z isomer. Rhodanine-based photoswitches therefore represent an easy to access and highly valuable molecular toolbox for implementing light responsiveness to the breadth of functional molecular systems.
Authors with CRIS profile
Laura Köttner
Lehrstuhl für Organische Chemie I
Friederike Wolff
Professur für Experimentelle Molekulare Zelldynamik
Esther Zanin
Professur für Experimentelle Molekulare Zelldynamik
Henry Dube
Lehrstuhl für Organische Chemie I
Involved external institutions
Germany (DE)How to cite
APA:
Köttner, L., Wolff, F., Mayer, P., Zanin, E., & Dube, H. (2024). Rhodanine-Based Chromophores: Fast Access to Capable Photoswitches and Application in Light-Induced Apoptosis Autoren. Journal of the American Chemical Society, 146(3), 1894–1903. https://dx.doi.org/10.1021/jacs.3c07710
MLA:
Köttner, Laura, et al. "Rhodanine-Based Chromophores: Fast Access to Capable Photoswitches and Application in Light-Induced Apoptosis Autoren." Journal of the American Chemical Society 146.3 (2024): 1894–1903.
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