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Synthesis of an azido-tagged low affinity ratiometric calcium sensor.

Caldwell ST, Cairns AG, Olson M, Chalmers S, Sandison M, Mullen W, McCarron JG, Hartley RC - Tetrahedron (2015)

Bottom Line: The synthesis of a dual excitation, ratiometric calcium ion sensor with a K d 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 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.

View Article: PubMed Central - PubMed

Affiliation: WestCHEM School of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK.

ABSTRACT

Changes in high localised concentrations of Ca(2+) ions are fundamental to cell signalling. The synthesis of a dual excitation, ratiometric calcium ion sensor with a K d 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-oxidation-cyclisation 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.

No MeSH data available.


Related in: MedlinePlus

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Mentions: The final part of the synthesis required the incorporation of the thiohydantoin unit (Scheme 2). 3-Azidopropylamine 15 was prepared by the literature method,37 converted into an isothiocyanate and reacted with the methyl ester of glycine to give thiohydantoin 16.38 Knoevenagel condensation39 with aldehyde 14 completed the fluorophore 17 and saponification of the esters gave NitroAzidoFuraRed.


Synthesis of an azido-tagged low affinity ratiometric calcium sensor.

Caldwell ST, Cairns AG, Olson M, Chalmers S, Sandison M, Mullen W, McCarron JG, Hartley RC - Tetrahedron (2015)

© Copyright Policy - CC BY
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4660056&req=5

Mentions: The final part of the synthesis required the incorporation of the thiohydantoin unit (Scheme 2). 3-Azidopropylamine 15 was prepared by the literature method,37 converted into an isothiocyanate and reacted with the methyl ester of glycine to give thiohydantoin 16.38 Knoevenagel condensation39 with aldehyde 14 completed the fluorophore 17 and saponification of the esters gave NitroAzidoFuraRed.

Bottom Line: The synthesis of a dual excitation, ratiometric calcium ion sensor with a K d 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 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.

View Article: PubMed Central - PubMed

Affiliation: WestCHEM School of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK.

ABSTRACT

Changes in high localised concentrations of Ca(2+) ions are fundamental to cell signalling. The synthesis of a dual excitation, ratiometric calcium ion sensor with a K d 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-oxidation-cyclisation 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.

No MeSH data available.


Related in: MedlinePlus