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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.
Afiliación
  • Caldwell ST; WestCHEM School of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK.
  • Cairns AG; WestCHEM School of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK.
  • Olson M; Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, UK.
  • Chalmers S; Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, UK.
  • Sandison M; Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, UK.
  • Mullen W; BHF Glasgow Cardiovascular Research Centre, Institute of Cardiovascular and Medical Sciences, College of Medical Veterinary and Life Sciences, University of Glasgow, Glasgow G12 8QQ, UK.
  • McCarron JG; Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, UK.
  • Hartley RC; WestCHEM School of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK.
Tetrahedron ; 71(51): 9571-9578, 2015 Dec 23.
Article en En | MEDLINE | ID: mdl-26709317
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 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-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.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Tetrahedron Año: 2015 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Tetrahedron Año: 2015 Tipo del documento: Article Pais de publicación: Reino Unido