bio-conjugates is observed in aqueous buffers without adding
aggregate disrupting additives.
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Conclusion and future work
In summary, a promising new class of water-soluble fluores-
cent labels based on a di-styryl E-BODIPY scaffold, has been
developed. The use of sequential derivatisations of its N,N-
dimethylpropargylamine linker arms and meso-phenyl carboxylic
acid with 1,3-propanesultone and the dipeptide (a-sulfo-b-
alanine)2 has led for the first time to a poly-sulfonated red-emitting
BODIPY dye which does not aggregate in aqueous solutions.
The successful post-synthetic sulfonation of highly-functionalised
BODIPY cores clearly demonstrates the versatility of this easy-to-
implement water-solubilising method. In this context, we believe
that this procedure has a strong potential to enhance the water
solubility of promising but highly hydrophobic fluorescent and/or
redox active multi-component systems such as “cascatelle” dyes24
or through-bond energy transfer cassettes.25 As proteins labels,
water-soluble BODIPY dyes, such as 9, are more or less equivalent
to the commercial sulfoindocyanine dye Cy 5.0. However, to im-
prove the brightness of the resulting BODIPY–protein conjugates,
further sulfonation of our water-soluble derviatives in the 2- and
6-positions through the Boyer–Burgess method11,26 and/or the
size increase of the BODIPY bio-conjugatable linker are currently
under investigation.
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Acknowledgements
17 C. Goze, G. Ulrich and R. Ziessel, Org. Lett., 2006, 8, 4445.
18 M. S. T. Goncalves, Chem. Rev., 2009, 109, 190.
This work was supported by the Agence Nationale de la Recherche
(Programme Blanc 2009, ANR-09-BLAN-0081-01) especially for
a PhD grant to Ce´drik Massif, La Re´gion Haute-Normandie
via the CRUNCh program (CPER 2007-2013), and Institut
Universitaire de France (IUF). We thank Dr Guillaume Clave´ for
the synthesis of sulfoindocyanine dye Cy 5.0, Dr Herve´ Volland
(iBiTecS, LERI, CEA-Saclay) for kind gift of anti-HA mAb clone
12CA5, and Professor Jack Harrowfield (CNRS-ISIS, Strasbourg)
for commenting on the manuscript before publication.
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