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https://hdl.handle.net/2440/99539
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Type: | Journal article |
Title: | Photoregulation of α-chymotrypsin activity by spiropyran-based inhibitors in solution and attached to an optical fiber |
Other Titles: | Photoregulation of alpha-chymotrypsin activity by spiropyran-based inhibitors in solution and attached to an optical fiber |
Author: | Zhang, X. Heng, S. Abell, A. |
Citation: | Chemistry: A European Journal, 2015; 21(30):10703-10713 |
Publisher: | Wiley |
Issue Date: | 2015 |
ISSN: | 0947-6539 1521-3765 |
Statement of Responsibility: | Xiaozhou Zhang, Sabrina Heng, Andrew. D. Abell |
Abstract: | Here the synthesis and characterization of a new class of spiropyran-based protease inhibitor is reported that can be reversibly photoswitched between an active spiropyran (SP) isomer and a less active merocyanine (MC) isomer upon irradiation with UV and visible light, respectively, both in solution and on a surface of a microstructured optical fiber (MOF). The most potent inhibitor in the series (SP-3 b) has a C-terminal phenylalanyl-based α-ketoester group and inhibits α-chymotrypsin with a Ki of 115 nM. An analogue containing a C-terminal Weinreb amide (SP-2 d) demonstrated excellent stability and photoswitching in solution and was attached to the surface of a MOF. The SP isomer of Weinreb amide 2 d is a competitive reversible inhibitor in solution and also on fiber, while the corresponding MC isomer was significantly less active in both media. The ability of this new class of spiropyran-based protease inhibitor to modulate enzyme activity on a MOF paves the way for sensing applications. |
Keywords: | enzymes; peptidomimetics; photoswitching, spiropyran; surface chemistry |
Rights: | © 2015 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim |
DOI: | 10.1002/chem.201501488 |
Published version: | http://dx.doi.org/10.1002/chem.201501488 |
Appears in Collections: | Aurora harvest 7 IPAS publications |
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