A novel water‐soluble fluorescent probe: Synthesis, luminescence and biological properties of the sodium salt of the 4‐sulfonato‐3,3′,5,5′‐tetramethyl‐2,2′‐pyrromethen‐1,1′‐BF₂ complex

Abstract

et al. / A novel water-soluble fluorescent probe Mass spectrometry. (5-I3C)-Retinal: m/z 285 (M + ); I3C incorporation calcd. from the mass spectra: 85%; exact mass calcd. for '3C,,'3CH,,0: 258.2174; found: 285.2164. ( 18-'3C)-Retinal: m/z 285 ( M + ) ; I3C incorporation calcd. from the mass spectra: 92.4%.from the Netherlands Organization for the Advancement of Pure Research (ZWO). The authors wich to hank Drs. C. Erkelens and Mr. F. Lefeber for recording the NMR spectra and Mr. J . J. van Houte for recording the mass spectra. The manuscript was reviewed by Miss S. Amadio.Abstract. The reaction of the 3,3',5,5'-tetramethyI-2,2'-pyrromethen-1,l '-BF, complex with chlorosulfonic acid and its subsequent neutralisation with sodium bicarbonate yields the titled compound 1, which, in addition to appropriate thermal and photochemical stability, possesses excellent fluorescent properties. As a preliminary assay of its potential usefulness as a fluorescent probe in medical and biological research, the chemical was administered intravenously to rats and possible signs of toxicity were recorded. The rats showed no apparent detrimental effects and excreted the compound in the urine within three hours. In tests in which Salmonella and E. coli strains were used as indicators of genotoxicity, no mutagenic effects were observed.

Diaroyl(methanato)boron Difluoride Compounds as Medium‐Sensitive Two‐Photon Fluorescent Probes

“…[12] Aiming at keeping the satisfactory aspects of the BODIPY chromophores while improving their features toward two-photon absorption, we became interested in a series of diaroyl(methanato)boron difluoride compounds (Ar 1 Ar 2 BF 2 1±9), with structures related to BODIPY (Scheme 1). b-Diketone±boron difluoride complexes have been known for more than 75 years; [13] nevertheless, the diaroyl series remains largely unexplored, excepting the investigations performed on the parent compound of this series, dibenzoyl(methanato)boron difluoride (9), whose emission [14,15] and reactivity [16] of the singlet excited state have been investigated. Some related compounds were reported to exhibit attractive absorption and emission features, such as large molar absorption coefficients, or large fluorescence quantum yields.…”

Physical and Photophysical Characterization of a BODIPY Phosphatidylcholine as a Membrane Probe

“…Because of these desirable properties, BODIPY fluorophores have found wide application for studying the solution structure of proteins (Bergström et al, 1999), for assaying enzymes and for imaging (Farber et al, 2001). BODIPY fluorophores are generally nontoxic to cells (Wories et al, 1985) and can be used to study lipid metabolism (Kasurinen, 1992), lipid transport (Pagano et al, 1999), and to diagnose diseases (Chen et al, 1999).…”

Aza-BODIPY dyes with enhanced hydrophilicity

“…Sometime ago we refined 11 a procedure 12, 13 for adding sulfonic acid groups into the BODIPY 2- and 6-positions, that gave the water-soluble BODIPY dye C . Consequently, it seemed logical to apply the same approach to obtain the aza-BODIPY disulfonic acid D .…”