Synthesis of an azido-tagged low affinity ratiometric calcium sensor

TETRAHEDRON

卷:71

Article

Caldwell, Stuart T.¹  Cairns, Andrew G.¹  Olson, Marnie²  Chalmers, Susan²  Sandison, Mairi²  Mullen, William³  McCarron, John G.²  Hartley, Richard C.¹ 

[1] Univ Glasgow, WestCHEM Sch Chem, Glasgow G12 8QQ, Lanark, Scotland

[2] Univ Strathclyde, Strathclyde Inst Pharm & Biomed Sci, Glasgow G4 0RE, Lanark, Scotland

[3] Univ Glasgow, Coll Med Vet & Life Sci, Inst Cardiovasc & Med Sci, BHP Glasgow Cardiovasc Res Ctr, Glasgow G12 8QQ, Lanark, Scotland

关键词: Calcium;    Thiohydantoin;    BAPTA;    Fluorescence;    Bioorthogonal;   

DOI  :  10.1016/j.tet.2015.10.052

来源: Elsevier

【 摘 要 】

Changes in high localised concentrations of Ca2+ ions are fundamental to cell signalling. The synthesis of a dual excitation, ratiometric calcium ion sensor with a K-d of 90 mu M, 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. (C) 2015 The Authors. Published by Elsevier Ltd.

【 授权许可】

Free