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Vorträge und Posterpräsentationen (mit Tagungsband-Eintrag):

R. Oliveira Conceição, M.D. Mihovilovic:
"Synthesis Of Double-Click Azobenzenes For An Easy Functionalization Of Biomolecules";
Poster: 21st European Symposium on Organic Chemistry, Wien; 14.07.2019 - 18.07.2019; in: "21st European Symposium on Organic Chemistry", (2019), S. 128.



Kurzfassung englisch:
The control of a bioactive compound´s activity is of crucial importance in the fields of medicine and biology. Photopharmacology offers the possibility of obtaining this control by using light, an external, non-toxic and orthogonal stimulus which can be quantitatively and qualitatively regulated, as well as spatially and temporally controlled. More concretely, in photopharmacology the bioactive compound is covalently bound to a photoswitch, a chemical entity that suffers a reversible chemical transformation after the absorption of one photon. Consequently, the physical properties of the bioactive compound will be different before and after irradiation resulting in a different ability to interact with its target. 1,2
Several photoswitches such as azobenzenes, hemithioindigos, stilbenes, diarylethenes, spiropyrans, thiophenefulgides and, more recently, donor-acceptor Stenhouse adducts are available.3,4 Among all of these, azobenzenes, which reversibly isomerize between the trans and the cis conformation, are probably the most well-studied. Due to their high quantum yields, fast photoisomerization rates and resistance to optical fatigue, they have been used in the study of ion-channels, GABAA and Glutamate receptors, for example.5-7
In this work, we aim to offer a simple, fast and selective way of functionalizing a biomolecule with an azobenzene, by taking advantage of click chemistry. Several photoswitches containing 2 different click chemistry moieties were synthesized, allowing a selective covalent bond to 1 or 2 different molecules. In addition, the photophysical properties of this molecules were studied. This library allows to choose, from a variety of molecules, at least one which is suitable for the desired application according to the photophysical properties and click moieties.

1. Velema, W. A., Szymanski, W. & Feringa, B. L. Photopharmacology : beyond proof of principle Photopharmacology : beyond proof of principle. J. Am. Chem. Soc. 126, 2178 (2014).
2. Lerch, M. M., Hansen, M. J., van Dam, G. M., Szymanski, W. & Feringa, B. L. Emerging Targets in Photopharmacology. Angew. Chem. Int. Ed. 55, 10978-10999 (2016).
3. Beierle, J. M., Kistemaker, H. A. V, Velema, W. A. & Feringa, B. L. Reversible Photocontrol of Biological Systems by the Incorporation of Molecular Photoswitches. Chem. Rev. 113, 6114-6178 (2013).
4. Szymański, W., Feringa, B. L. & Lerch, M. M. The (photo)chemistry of Stenhouse photoswitches: guiding principles and system design. Chem. Soc. Rev. 47, (2018).
5. Banghart, M., Borges, K., Isacoff, E., Trauner, D. & Kramer, R. H. Light-activated ion channels for remote control of neuronal firing. Nat. Neurosci. 7, 1381-1386 (2004).
6. Stein, M. et al. Azo-Propofols : Photochromic Potentiators of GABA A Receptors **. Angew. Chem. Int. Ed. 51, 10500-10504 (2012).
7. Volgraf, M. et al. Reversibly Caged Glutamate : A Photochromic Agonist of Ionotropic Glutamate Receptors. J. Am. Chem. Soc. 250, 260-261 (2007).


Elektronische Version der Publikation:
https://publik.tuwien.ac.at/files/publik_286002.pdf


Erstellt aus der Publikationsdatenbank der Technischen Universität Wien.