Caldwell, S. T. , Cairns, A. G., Olson, M., Chalmers, S., Sandison, M., Mullen, W. , McCarron, J. G. and Hartley, R. C. (2015) Synthesis of an azido-tagged low affinity ratiometric calcium sensor. Tetrahedron, 71(51), pp. 9571-9578. (doi: 10.1016/j.tet.2015.10.052) (PMID:26709317) (PMCID:PMC4660056)
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Abstract
Changes in high localized concentrations of Ca2+ ions are fundamental to cell signalling. The synthesis of a dual excitation, ratiometric calcium ion sensor with a Kd of 90 μM, is described. It is tagged with an azido group for bioconjugation, and absorbs in the blue/green and emits in the red region of the visible spectrum with a large Stokes shift. The binding modulating nitro group is introduced to the BAPTA core prior to construction of a benzofuran-2-yl carboxaldehyde by an allylation-oxdiation-cyclization sequence, which is followed by condensation with an azido-tagged thiohydantoin. The thiohydantoin unit has to be protected with an acetoxymethyl (AM) caging group to allow CuAAC click reaction and incorporation of the KDEL peptide endoplasmic reticulum (ER) retention sequence.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Caldwell, Dr Stuart and Sandison, Dr Mairi and Cairns, Mr Andrew and Hartley, Professor Richard and Mullen, Dr Bill |
| Authors: | Caldwell, S. T., Cairns, A. G., Olson, M., Chalmers, S., Sandison, M., Mullen, W., McCarron, J. G., and Hartley, R. C. |
| College/School: | College of Medical Veterinary and Life Sciences > School of Cardiovascular & Metabolic Health College of Science and Engineering > School of Chemistry College of Science and Engineering > School of Engineering > Biomedical Engineering |
| Journal Name: | Tetrahedron |
| Publisher: | Elsevier |
| ISSN: | 0040-4020 |
| ISSN (Online): | 1464-5416 |
| Published Online: | 20 October 2015 |
| Copyright Holders: | Copyright © 2015 The Authors |
| First Published: | First published in Tetrahedron 71(5):9571-9578 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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