Rustler, Karin and Mickert, Matthias J. and Nazet, Julian and Merkl, Rainer and Gorris, Hans H. and Koenig, Burkhard (2018) Development of photoswitchable inhibitors for beta-galactosidase. ORGANIC & BIOMOLECULAR CHEMISTRY, 16 (40). pp. 7430-7437. ISSN 1477-0520, 1477-0539
Full text not available from this repository. (Request a copy)Abstract
Azobenzenes are of particular interest as a photochromic scaffold for biological applications because of their high fatigue resistance, their large geometrical change between extended (trans) and bent (cis) isomer, and their diverse synthetic accessibility. Despite their wide-spread use, there is no reported photochromic inhibitor of the well-investigated enzyme -galactosidase, which plays an important role for biochemistry and single molecule studies. Herein, we report the synthesis of photochromic competitive -galactosidase inhibitors based on the molecular structure of 2-phenylethyl -d-thiogalactoside (PETG) and 1-amino-1-deoxy--d-galactose (-d-galactosylamine). The thermally highly stable PETG-based azobenzenes show excellent photochromic properties in polar solvents and moderate to high photostationary states (PSS). The optimized compound 37 is a strong competitive inhibitior of -galactosidase from Escherichia coli and its inhibition constant (K-i) changes between 60 nM and 290 nM upon irradiation with light. Additional docking experiments supported the observed structure-activity relationship.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | POTENT GLYCOSIDASE INHIBITORS; IONOTROPIC GLUTAMATE-RECEPTOR; LIGHT ACTIVATION; OPTICAL CONTROL; EMERGING CLASS; BLIND MICE; ENZYME; AZOBENZENE; AMINO(HYDROXYMETHYL)CYCLOPEN-TANETRIOLS; PHOTOREGULATION; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 500 Science > 570 Life sciences |
| Divisions: | Biology, Preclinical Medicine > Institut für Biophysik und physikalische Biochemie > Prof. Dr. Rainer Merkl Chemistry and Pharmacy > Institut für Analytische Chemie, Chemo- und Biosensorik Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 04 Dec 2019 12:53 |
| Last Modified: | 04 Dec 2019 12:53 |
| URI: | https://pred.uni-regensburg.de/id/eprint/13672 |
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