Wu, Liangxing (2009-08). Design, Syntheses and Applications of Fluorescent Dyes. Doctoral Dissertation. Thesis uri icon

abstract

  • New methodologies for the efficient syntheses of 4,4-difluoro-4-bora-3a,4adiaza- s-indacenes (BODIPYs) and rosamines were developed. A serendipitous discovery led to a new reaction which afforded BODIPYs in high yields. Systematic studies of the kinetics and mechanisms of the new reaction were performed. A series of BODIPYs were successfully prepared using the new approach. A simple and efficient synthesis of rosamines with cyclic-amine substituents was devised. These new rosamines showed interesting anti-tumor activities. Several types of novel fluorescent compounds were prepared. Highly fluorescent GFP-chromophore analogs were designed and synthesized. The correlation between the optical properties and the structures was investigated. New pyronin dyes with mesoheteroatom substituents were efficiently prepared. The fluorescence properties of these compounds were highly dependent on the nature of the meso-substituents. A set of BODIPY dyes that fluoresce brightly above 600 nm were made. They were then used as acceptors to prepare water-soluble through-bond energy transfer cassettes. All the cassettes had complete energy transfer and high quantum yields in MeOH. A few also had good fluorescence properties in aqueous media and even on proteins. The through-bond energy transfer cassettes were used to monitor protein-protein interactions. In order to test our hypothesis, an artificial protein interaction system was built by utilizing the biotin/(strept)avidin interactions. Thus Atto425-BSA-biotin, streptavidin-cassette1 and avidin-cassette2 were prepared. The interactions between Atto425-BSA-biotin and cassette labeled (strept)avidin were successfully detected in vitro and in living cells by fluorescence techniques.
  • New methodologies for the efficient syntheses of 4,4-difluoro-4-bora-3a,4adiaza-
    s-indacenes (BODIPYs) and rosamines were developed. A serendipitous discovery
    led to a new reaction which afforded BODIPYs in high yields. Systematic studies of the
    kinetics and mechanisms of the new reaction were performed. A series of BODIPYs
    were successfully prepared using the new approach. A simple and efficient synthesis of
    rosamines with cyclic-amine substituents was devised. These new rosamines showed
    interesting anti-tumor activities.
    Several types of novel fluorescent compounds were prepared. Highly fluorescent
    GFP-chromophore analogs were designed and synthesized. The correlation between the
    optical properties and the structures was investigated. New pyronin dyes with mesoheteroatom
    substituents were efficiently prepared. The fluorescence properties of these
    compounds were highly dependent on the nature of the meso-substituents. A set of
    BODIPY dyes that fluoresce brightly above 600 nm were made. They were then used as
    acceptors to prepare water-soluble through-bond energy transfer cassettes. All the
    cassettes had complete energy transfer and high quantum yields in MeOH. A few also
    had good fluorescence properties in aqueous media and even on proteins.
    The through-bond energy transfer cassettes were used to monitor protein-protein
    interactions. In order to test our hypothesis, an artificial protein interaction system was
    built by utilizing the biotin/(strept)avidin interactions. Thus Atto425-BSA-biotin,
    streptavidin-cassette1 and avidin-cassette2 were prepared. The interactions between
    Atto425-BSA-biotin and cassette labeled (strept)avidin were successfully detected in
    vitro and in living cells by fluorescence techniques.

publication date

  • August 2009