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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Zhang, Xiaozhou Abell, Andrew D. Heng, Sabrina |
| Description | Author Affiliation: Zhang X ( ARC Centre of Excellence for Nanoscale BioPhotonics, Institute for Photonics and Advanced Sensing and Department of Chemistry, The University of Adelaide, South Australia, 5005 (Australia).); Heng S ( ARC Centre of Excellence for Nanoscale BioPhotonics, Institute for Photonics and Advanced Sensing and Department of Chemistry, The University of Adelaide, South Australia, 5005 (Australia).); Abell AD ( ARC Centre of Excellence for Nanoscale BioPhotonics, Institute for Photonics and Advanced Sensing and Department of Chemistry, The University of Adelaide, South Australia, 5005 (Australia). andrew.abell@adelaide.edu.au.) |
| 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 $K_{i}$ 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. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 30 |
| Volume Number | 21 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2015-07-20 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Benzopyrans Chemistry Chymotrypsin Antagonists & Inhibitors Indoles Nitro Compounds Protease Inhibitors Animals Pharmacology Metabolism Isomerism Molecular Docking Simulation Optical Fibers Photochemical Processes Ultraviolet Rays |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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