Live-cell imaging with water-soluble aminophenoxazinone dyes synthesised through laccase biocatalysis.
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.
Bruyneel
Frédéric
F
Institute of Condensed Matter and Nanosciences (IMCN), Organic and Medicinal Chemistry Unit (CHOM), Université catholique de Louvain, Bâtiment Lavoisier, Place Louis Pasteur 1, 1348 Louvain-la-Neuve Belgium.
D'Auria
Ludovic
L
Payen
Olivier
O
Courtoy
Pierre J
PJ
Marchand-Brynaert
Jacqueline
J
D000818:Animals; D055162:Biocatalysis; D016466:CHO Cells; D002118:Calcium / Q000737:chemistry; D006224:Cricetinae; D003412:Cricetulus; D005456:Fluorescent Dyes / Q000737:chemistry / Q000378:metabolism*; D042845:Laccase / Q000378:metabolism*; D008274:Magnesium / Q000737:chemistry; D008856:Microscopy, Fluorescence; D010078:Oxazines / Q000737:chemistry / Q000378:metabolism*; D014867:Water / Q000737:chemistry
D005456:Fluorescent Dyes; D010078:Oxazines; D014867:Water; C020456:phenoxazinone; D042845:Laccase; D008274:Magnesium; D002118:Calcium