title: Synthesis of water-soluble red-emitting thienyl-BODIPYs and bovine serum albumin labeling.
abstract: The synthesis of three red-emitting and water-soluble thienyl-BODIPYs has been achieved. The trimethyl(propargyl)ammonium group was chosen as a vector for water solubility. One or two cationic arms were introduced either on the 2-position of the thienyl unit or on the 4-position on the boron atom. These dyes have pronounced absorption around 600 nm and intense emission at 650 nm with quantum yield of about 60% in water. Grafting of such BODIPYs via a flexible arm to BSA is very efficient, 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 PBS buffer is measured.
authors.affiliation: Laboratoire de Chimie Organique et Spectroscopies Avancées (LCOSA), ICPEES-LCOSA, UMR 7515 CNRS/Université de Strasbourg, École Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087 Strasbourg Cedex 02 (France), Fax: (+33) 3-68-85-27-61.
authors.forename: Arnaud
authors.initials: A
authors.lastname: Poirel
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Antoinette
authors.initials: A
authors.lastname: De Nicola
authors.forename: Raymond
authors.initials: R
authors.lastname: Ziessel
mesh_terms: D000818:Animals; D001896:Boron Compounds / Q000737:chemistry*; D002417:Cattle; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D012710:Serum Albumin, Bovine / Q000737:chemistry* / Q000378:metabolism; D012995:Solubility; D014867:Water / Q000737:chemistry
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D014867:Water; D012710:Serum Albumin, Bovine
keywords: bioconjugation; borondipyrromethene; dyes; fluorescent probes; water solubility