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

doi:10.1016/j.tet.2015.10.052

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

Strathclyde Institute Of Pharmacy And Biomedical Sciences

Research output: Contribution to journal › Article › peer-review

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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.

Original language	English
Pages (from-to)	9571–9578
Number of pages	8
Journal	Tetrahedron
Volume	71
Issue number	51
Early online date	20 Oct 2015
DOIs	https://doi.org/10.1016/j.tet.2015.10.052
Publication status	Published - 23 Dec 2015

Keywords

calcium
thiohydantoin
BAPTA
fluorescence
bioorthogonal

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10.1016/j.tet.2015.10.052

Caldwell-etal-Tetrahedron2015-synthesis-of-an-azido-tagged-low-affinity-ratiometric-calcium-sensorFinal published version, 719 KBLicence: CC BY 4.0

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@article{3d52f340bd2045188ebc25670ec6952b,

title = "Synthesis of an azido-tagged low affinity ratiometric calcium sensor",

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.",

keywords = "calcium, thiohydantoin, BAPTA, fluorescence, bioorthogonal",

author = "Caldwell, {Stuart T.} and Cairns, {Andrew G.} and Marnie Olson and Susan Chalmers and Mairi Sandison and William Mullen and McCarron, {John G.} and Hartley, {Richard C.}",

year = "2015",

month = dec,

day = "23",

doi = "10.1016/j.tet.2015.10.052",

language = "English",

volume = "71",

pages = "9571–9578",

journal = "Tetrahedron",

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publisher = "Elsevier Limited",

number = "51",

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T1 - Synthesis of an azido-tagged low affinity ratiometric calcium sensor

AU - Caldwell, Stuart T.

AU - Cairns, Andrew G.

AU - Olson, Marnie

AU - Chalmers, Susan

AU - Sandison, Mairi

AU - Mullen, William

AU - McCarron, John G.

AU - Hartley, Richard C.

PY - 2015/12/23

Y1 - 2015/12/23

N2 - 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.

AB - 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.

KW - calcium

KW - thiohydantoin

KW - BAPTA

KW - fluorescence

KW - bioorthogonal

UR - http://www.sciencedirect.com/science/journal/00404020

U2 - 10.1016/j.tet.2015.10.052

DO - 10.1016/j.tet.2015.10.052

M3 - Article

SN - 0040-4020

VL - 71

SP - 9571

EP - 9578

JO - Tetrahedron

JF - Tetrahedron

IS - 51

ER -

Synthesis of an azido-tagged low affinity ratiometric calcium sensor

Abstract

Keywords

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Susan Chalmers

Targeting Ca2 + Signals in intact native smooth muscle cells

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Synthesis of an azido-tagged low affinity ratiometric calcium sensor

Abstract

Keywords

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Susan Chalmers

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Targeting Ca2 + Signals in intact native smooth muscle cells

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