Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 10, Pages 2995-2999Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201411274
Keywords
dyes; pigments; fluorescence; imaging agents; proteins; synthetic methods
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Funding
- Institut Universitaire de France (IUF)
- Burgundy region (FABER programme, PARI Action 6, SSTIC 6 Imagerie, instrumentation, chimie et applications biomedicales)
- French Government through the French National Research Agency (ANR) [ANR-10-EQPX-05-01/IMAPPI Equipex]
- Fondation de Cooperation Scientifique Bourgogne Franche-Comte
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The preparation of highly water-soluble and strongly fluorescent diketopyrrolopyrrole (DPP) dyes using an unusual taurine-like sulfonated linker has been achieved. Exchanging a phenyl for a thienyl substituent shifts the emission wavelength to near =600nm. The free carboxylic acid group present in these new derivatives was readily activated and the dyes were subsequently covalently linked to a model protein (bovine serum albumin; BSA). The bioconjugates were characterized by electronic absorption, fluorescence spectroscopy and MALDI-TOF mass spectrometry, thus enabling precise determination of the labeling density (ratio DPP/BSA about 3 to 8). Outstanding values of fluorescence quantum yield (30% to 59%) for these bioconjugates are obtained. The photostability of these DPP dyes is considerably greater than that of fluorescein under the same irradiation conditions. Remarkably low detection limits between 80 and 300molecules/m(2) were found for the BSA bioconjugates by fluorescence imaging with a epifluorescence microscope.
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