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Live‐Cell Imaging with Water‐Soluble Aminophenoxazinone Dyes Synthesised through Laccase Biocatalysis
Author(s) -
Bruyneel Frédéric,
D'Auria Ludovic,
Payen Olivier,
Courtoy Pierre. J.,
MarchandBrynaert Jacqueline
Publication year - 2010
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201000145
Subject(s) - biocatalysis , laccase , chromophore , fluorescence , chemistry , live cell imaging , regioselectivity , quenching (fluorescence) , combinatorial chemistry , photochemistry , organic chemistry , enzyme , biochemistry , cell , catalysis , reaction mechanism , physics , quantum mechanics
Aminophenoxazinone dyes with variable water solubilities were assayed for the first time in a live‐cell imaging application. Among a library of ten sulfonylated chromophores, one compound gave excellent results as an endocytic marker, showing a precise subcellular distribution. The compound was compared to four commercial vital tracers, including Lucifer Yellow. The first laccase‐mediated regioselective synthesis of a diphosphorylated 2‐aminophenoxazinone dye was also described. This compound, water‐soluble at 10 −2 M , displayed modest fluorescence properties and the ability to complex Mg 2+ and Ca 2+ cations, therefore giving fluorescence quenching.