Journal
TETRAHEDRON LETTERS
Volume 55, Issue 50, Pages 6764-6768Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.10.054
Keywords
Activatable probes; Azo dyes; Bioconjugation; Dark quenchers; FRET
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Funding
- INSA Rouen
- Rouen University
- CNRS
- Labex SynOrg [ANR-11-LABX-0029]
- region Haute-Normandie (CRUNCh network)
- FEDER (TRIPODE) [33883]
- Institut Universitaire de France (IUF)
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A further extension of the efficient synthetic methodology described in Part I, to the aromatic bis-diazo scaffold of Black Hole Quencher-2 dye is presented. Bioconjugatable derivatives bearing either azido, terminal alkyne, or maleimide reactive group were easily obtained as well as the free-phenol form of BlackBerry (R) Quencher 650 (BBQ-650 (R)) initially developed by Berry & Associates, Inc. Company. The efficient conjugation ability of azido- and maleimide-quenchers was demonstrated through the facile preparation of the first water-soluble and formylated BHQ-2 dyes and a FRET-based probe suitable for the in vitro/in cellulo detection of a cancer-associated protease namely urokinase-type plasminogen activator. (C) 2014 Elsevier Ltd. All rights reserved.
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