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https://hdl.handle.net/2440/61873
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Type: | Journal article |
Title: | Structural optimization of photoswitch ligands for surface attachment of α-chymotrypsin and regulation of its surface binding |
Other Titles: | Structural optimization of photoswitch ligands for surface attachment of alpha-chymotrypsin and regulation of its surface binding |
Author: | Pearson, D. Abell, A. |
Citation: | Chemistry: A European Journal, 2010; 16(23):6983-6992 |
Publisher: | Wiley-V C H Verlag GMBH |
Issue Date: | 2010 |
ISSN: | 0947-6539 1521-3765 |
Statement of Responsibility: | David Pearson and Andrew D. Abell |
Abstract: | A modified gold surface that allows photoregulated binding of alpha-chymotrypsin has previously been reported. Here the development of this surface is reported, through the synthesis of a series of trifluoromethyl ketones and alpha-keto esters containing the azobenzene group and a surface attachment group as photoswitch inhibitors of alpha-chymotrypsin. All of the compounds are inhibitors of the enzyme, with activity that can be modulated by photoisomerization. The best photoswitch shows a reversible change in IC(50) inhibition constant of >5.3 times on photoisomerization. The trifluoromethyl ketone 1 exhibited excellent photoswitching and was attached to a gold surface in a two-step procedure involving an azide-alkyne cycloaddition. The resulting modified surface bound alpha-chymotrypsin to a degree that could be modulated by UV/Vis irradiation, showing "slow-tight" enzyme binding as observed for inhibitors in solution. |
Keywords: | azo compounds enzyme inhibitors photoswitching surface chemistry surface plasmon resonance |
Rights: | Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
DOI: | 10.1002/chem.200903369 |
Grant ID: | http://purl.org/au-research/grants/arc/DP0771901 http://purl.org/au-research/grants/arc/DP0771901 |
Published version: | http://dx.doi.org/10.1002/chem.200903369 |
Appears in Collections: | Aurora harvest Chemistry publications IPAS publications |
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