University of SaskatchewanHARVEST
  • Login
  • Submit Your Work
  • About
    • About HARVEST
    • Guidelines
    • Browse
      • All of HARVEST
      • Communities & Collections
      • By Issue Date
      • Authors
      • Titles
      • Subjects
      • This Collection
      • By Issue Date
      • Authors
      • Titles
      • Subjects
    • My Account
      • Login
      JavaScript is disabled for your browser. Some features of this site may not work without it.
      View Item 
      • HARVEST
      • Electronic Theses and Dissertations
      • Graduate Theses and Dissertations
      • View Item
      • HARVEST
      • Electronic Theses and Dissertations
      • Graduate Theses and Dissertations
      • View Item

      Design and Synthesis of Custom Styryl BODIPY Dyes for Bimodal Imaging

      Thumbnail
      View/Open
      MEHLHORN-THESIS-2022.pdf (6.536Mb)
      Date
      2022-07-29
      Author
      Mehlhorn, Hillary H
      Type
      Thesis
      Degree Level
      Masters
      Metadata
      Show full item record
      Abstract
      Innovation towards new agents for combined positron emission tomography/optical imaging is of significance for making advances in patient diagnosis. As of recent, boron-dipyrromethene (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene, BODIPY) dyes have shown promise as bimodal imaging agents serving as a fluorescent tag with capability to act as a fluorine-18 radiotracer. However, due the sensitivity of these molecules their chemical transformations are poorly understood. In this thesis, I address the synthetic challenge of near-infrared, “clickable” BODIPY dyes with complex functionality in order to identify reliable syntheses. Early investigation was concentrated on understanding the intricacies of BODIPY synthesis; in particular, the low yielding incorporation of boron difluoride. Conventional one-pot procedures were revised, and it was found that isolating the dipyrromethene scaffold followed by boron complexation improved the yield overall. In addition, aqueous work up procedures were modified to avoid the decomplexation of boron difluoride from the BODIPY product by vacuum-assisted removal of excess boron trifluoride. Robust synthetic procedures were established to afford the azido- functionalized BODIPY, which is valuable for tagging novel BODIPY dyes to disease-targeting vectors using “Click Chemistry”. The latter of the thesis focused on improving the water-solubility of the conjugated BODIPY dyes by addition of ionizable groups which can also partake in hydrogen bonding, making them suitable for biological application. It was found that the BODIPY molecule could not withstand ester hydrolysis conditions needed to produce diacid BODIPY derivatives. Alternatively, a Knoevenagel-like condensation provided two near-infrared BODIPY dyes, one bearing dihydroxy (phenolic) functionality demonstrating partial water-solubility. The dyes were characterized as long wavelength dyes to compliment future Price group studies.
      Degree
      Master of Science (M.Sc.)
      Department
      Chemistry
      Program
      Chemistry
      Supervisor
      Price, Eric W
      Committee
      George, Graham; Badea, Ildiko; Gravel, Michel
      Copyright Date
      2022
      URI
      https://hdl.handle.net/10388/14068
      Subject
      BODIPY
      near-infrared dye
      NIR dye
      BODIPY synthesis
      bimodal imaging
      PET imaging
      optical imaging
      Collections
      • Graduate Theses and Dissertations
      University of Saskatchewan

      University Library

      The University of Saskatchewan's main campus is situated on Treaty 6 Territory and the Homeland of the Métis.

      © University of Saskatchewan
      Contact Us | Disclaimer | Privacy