Synthesis of an azido-tagged low affinity ratiometric calcium sensor

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:Mullen, Dr Bill and Caldwell, Dr Stuart and Sandison, Dr Mairi and Cairns, Mr Andrew and Hartley, Professor Richard
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 > Institute of Cardiovascular and Medical Sciences
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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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
537551Targeting Ca2+ Signals in intact native smooth muscleRichard HartleyWellcome Trust (WELLCOME)WT0922292MACHEM - CHEMISTRY
419371Quota doctoral training account (DTA)Graeme CookeBiotechnology and Biological Sciences Research Council (BBSRC)BB/D526310/1CHEM - CHEMISTRY