Synthesis, spectroscopic properties and protein labeling of water soluble 3,5-disubstituted boron dipyrromethenes

Sulfur-containing 3,5-disubstituted boron dipyrromethene (Bodipy®) fluorescent probes with improved water solubility were synthesized. A dicarboxylic acid derivative that can be excited by the 543nm HeNe laser line is very soluble in aqueous solution and retains high fluorescence quantum yield of th...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2009-12, Vol.19 (24), p.6911-6913
Main Authors: Dilek, Özlem, Bane, Susan L.
Format: Article
Language:English
Subjects:
Analytical, structural and metabolic biochemistry
Biological and medical sciences
Boron Compounds - chemical synthesis
Boron Compounds - chemistry
Boron dipyrromethenes
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Fundamental and applied biological sciences. Psychology
General aspects, investigation methods
Protein labeling
Proteins
Proteins - chemistry
Solubility
Spectrometry, Fluorescence
Water - chemistry
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Summary:Sulfur-containing 3,5-disubstituted boron dipyrromethene (Bodipy®) fluorescent probes with improved water solubility were synthesized. A dicarboxylic acid derivative that can be excited by the 543nm HeNe laser line is very soluble in aqueous solution and retains high fluorescence quantum yield of the unionizable parent molecule. Conversion of the dicarboxylic acid to the succimidyl or sulfosuccinimidyl diester produces molecules capable of labeling proteins with a bright and stable fluorescence signal.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2009.10.080