Water‐Soluble Red‐Emitting Distyryl‐Borondipyrromethene (BODIPY) Dyes for Biolabeling |
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| Authors: | Dr Song‐lin Niu Cédrik Massif Dr Gilles Ulrich Prof Pierre‐Yves Renard Dr Anthony Romieu Dr Raymond Ziessel |
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| Institution: | 1. Laboratoire de Chimie Moléculaire et Spectroscopies Avancées (LCOSA), LMSPC UMR 7515 au CRNS, Ecole Européenne de Chimie, Polymères et Matériaux, 25 rue Becquerel, 67087 Strasbourg Cedex 02 (France), Fax: (+33)?3‐68‐85‐27‐6;2. COBRA‐CNRS UMR 6014 & FR 3038 rue Lucien Tesnière, 76131 Mont‐Saint‐Aignan (France), Fax: (+33)?2‐35‐52‐29‐71;3. Université de Rouen, Place Emile Blondel, 76821 Mont‐Saint‐Aignan (France);4. Institut Universitaire de France, 103 Boulevard Saint‐Michel, 75005, Paris (France) |
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| Abstract: | A series of water‐soluble red‐emitting distyryl‐borondipyrromethene (BODIPY) dyes were designed and synthesized by using three complementary approaches aimed at introducing water‐solubilizing groups on opposite faces of the fluorescent core to reduce or completely suppress self‐aggregation. An additional carboxylic acid functional group was introduced at the pseudo‐meso position of the BODIPY scaffold for conjugation to amine‐containing biomolecules/biopolymers. The optical properties of these dyes were evaluated under simulated physiological conditions (i.e., phosphate‐buffered saline (PBS), pH 7.5) or in pure water. The emission wavelength (λmax) of these labels was found in the 640–660 nm range with quantum yields from modest to unprecedentedly high values (4 to 38 %). The bioconjugation of these distyryl‐BODIPY dyes with bovine serum albumin (BSA) and the monoclonal antibody (mAb) 12A5 was successfully performed under mild aqueous conditions. |
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| Keywords: | biolabeling BODIPYs fluorescence sulfonated linker water soluble |
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