Synthesis of an azido-tagged low affinity ratiometric calcium sensor

Stuart T. Caldwell, Andrew G. Cairns, Marnie Olson, Susan Chalmers, Mairi Sandison, William Mullen, John G. McCarron, Richard C. Hartley

Research output: Contribution to journalArticle

3 Citations (Scopus)

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.
LanguageEnglish
Pages9571–9578
Number of pages8
JournalTetrahedron
Volume71
Issue number51
Early online date20 Oct 2015
DOIs
Publication statusPublished - 23 Dec 2015

Fingerprint

Thiohydantoins
Calcium ion sensors
Allylation
Ions
Cell signaling
Calcium
Cyclization
Sensors
Endoplasmic Reticulum
Condensation
Peptides

Keywords

  • calcium
  • thiohydantoin
  • BAPTA
  • fluorescence
  • bioorthogonal

Cite this

Caldwell, S. T., Cairns, A. G., Olson, M., Chalmers, S., Sandison, M., Mullen, W., ... Hartley, R. C. (2015). Synthesis of an azido-tagged low affinity ratiometric calcium sensor. Tetrahedron, 71(51), 9571–9578. https://doi.org/10.1016/j.tet.2015.10.052
Caldwell, Stuart T. ; Cairns, Andrew G. ; Olson, Marnie ; Chalmers, Susan ; Sandison, Mairi ; Mullen, William ; McCarron, John G. ; Hartley, Richard C. / Synthesis of an azido-tagged low affinity ratiometric calcium sensor. In: Tetrahedron. 2015 ; Vol. 71, No. 51. pp. 9571–9578.
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Synthesis of an azido-tagged low affinity ratiometric calcium sensor. / Caldwell, Stuart T.; Cairns, Andrew G.; Olson, Marnie; Chalmers, Susan; Sandison, Mairi; Mullen, William; McCarron, John G.; Hartley, Richard C.

In: Tetrahedron, Vol. 71, No. 51, 23.12.2015, p. 9571–9578.

Research output: Contribution to journalArticle

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AU - Caldwell, Stuart T.

AU - Cairns, Andrew G.

AU - Olson, Marnie

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AU - Mullen, William

AU - McCarron, John G.

AU - Hartley, Richard C.

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