title: Water-soluble red-emitting distyryl-borondipyrromethene (BODIPY) dyes for biolabeling.
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 (λ(max)) 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.
authors.affiliation: 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.
authors.forename: Song-lin
authors.initials: SL
authors.lastname: Niu
authors.forename: Cédrik
authors.initials: C
authors.lastname: Massif
authors.forename: Gilles
authors.initials: G
authors.lastname: Ulrich
authors.forename: Pierre-Yves
authors.initials: PY
authors.lastname: Renard
authors.forename: Anthony
authors.initials: A
authors.lastname: Romieu
authors.forename: Raymond
authors.initials: R
authors.lastname: Ziessel
mesh_terms: D000911:Antibodies, Monoclonal / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004396:Coloring Agents; D005456:Fluorescent Dyes / Q000737:chemistry; D015394:Molecular Structure; D012710:Serum Albumin, Bovine / Q000737:chemistry; D012995:Solubility; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D000911:Antibodies, Monoclonal; D001896:Boron Compounds; D004396:Coloring Agents; D005456:Fluorescent Dyes; D013343:Styrenes; D014867:Water; D012710:Serum Albumin, Bovine