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Synthesis of Water‐Soluble Red‐Emitting Thienyl–BODIPYs and Bovine Serum Albumin Labeling
Author(s) -
Poirel Arnaud,
Retailleau Pascal,
De Nicola Antoinette,
Ziessel Raymond
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303988
Subject(s) - cationic polymerization , bovine serum albumin , chemistry , quantum yield , yield (engineering) , fluorescence , rose bengal , ammonium , absorption (acoustics) , solubility , photochemistry , grafting , nuclear chemistry , polymer chemistry , chromatography , organic chemistry , materials science , polymer , physics , quantum mechanics , metallurgy , composite material
Thesynthesis of three red‐emitting and water‐soluble thienyl‐BODIPYs has beenachieved. The trimethyl(propargyl)ammonium group was chosen as a vector forwater solubility. One or two cationic arms were introduced either on the2‐position of the thienyl unit or on the 4‐position on the boron atom. Thesedyes have pronounced absorption around 600 nm and intense emission at 650 nmwith quantum yield of about 60% in water. Grafting of such BODIPYs via a flexible arm to BSA is veryefficient, allowing attachment of 1 to 30 labels in a controlled manner. Very strong fluorescence (quantum yield 56%)without aggregation of the dye at a low loading ratio (1:5 BSA/label) in PBSbuffer is measured.