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Synthesis and Characterization of Novel Flavonoid-Based Fluorescent Sensors and other Sensors with Excited State Intramolecular Proton Transfer for Biological Applications

McDonald, Lucas J
http://rave.ohiolink.edu/etdc/view?acc_num=akron1524658238472646

Abstract Details

2018, Doctor of Philosophy, University of Akron, Integrated Bioscience.
Application of photophysical mechanisms, such as photoinduced electron transfer (ESIPT) and aggregate induced emission (AIE), have been used to gain valuable information in biological systems. Fluorophores are commonly capable of displaying more than one photophysical property and it can be difficult to distinguish between them. In chapter II a set of aluminum sensors were reported previously as AIE materials were further investigated for their potential to display ESIPT over AIE. Low temperature fluorescence was utilized to distinguish between their emissive tautomers, which allowed for differentiation between AIE and ESIPT emission. ESIPT was determined to be the primary source of emission. The development of a large variety of fluorescent materials that can selectively bind to zinc over other competitive metals such as cadmium has been heavily sought after for the last three decades. 2-(2’-Hydroxyphenyl)benzoxazole (HBO) can chelate Zn2+ and readily undergo ESIPT to display large Stokes shifts in excess of 100 nm. Large Stokes shifts can provide sensors with high resolution. Additionally, the formed zinc complex can selectively interact with pyrophosphate (PPi) over other phosphate molecules. Chapter III discusses a newly synthesized HBO-based material that displays good selectivity for zinc and reactivity with PPi over ATP and ADP. Chapters IV-VI presents several different synthesized flavonoids that have been successfully applied to a variety of different biological applications such as molecular probes and a non-specific contrast imaging stain for live muscle imaging, which has never been reported before. Additionally, investigation into how proteins, HSA and BSA, interact with several different flavonoids was performed in order to elucidate structural information about the flavonoid-protein complex. Chapter VII presents a developmental study of the zebrafish lateral line for 96 hpf and younger embryos using a newly synthesized styryl dye. This dye displays the ability to not only stain hair cells, but also the surrounding supporting cells of the neuromast. This dye displayed a large Stokes shift and emitted in the NIR region, which is unlike other commercially available dyes for neuromast staining. Additionally, neuromast destruction from neomycin, and subsequent regeneration, including the regeneration of the support cells was monitored in real-time with this dye.
Yi Pang (Advisor)
Wiley Youngs (Committee Member)
Leah Shriver (Committee Member)
Christopher Ziegler (Committee Member)
Richard Londraville (Committee Member)
200 p.
Biology; Chemistry
ESIPT; AIE; zebrafish; sarcomere; aluminum; zinc; pyrophosphate; ER; flavonoid; chemical sensors; molecular probes; HSA; BSA; native mass spectrometry; fluorescence; UV-vis; neuromasts; hair cells; support cells

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Citations

  • McDonald, L. J. (2018). Synthesis and Characterization of Novel Flavonoid-Based Fluorescent Sensors and other Sensors with Excited State Intramolecular Proton Transfer for Biological Applications [Doctoral dissertation, University of Akron]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=akron1524658238472646

    APA Style (7th edition)

  • McDonald, Lucas. Synthesis and Characterization of Novel Flavonoid-Based Fluorescent Sensors and other Sensors with Excited State Intramolecular Proton Transfer for Biological Applications. 2018. University of Akron, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=akron1524658238472646.

    MLA Style (8th edition)

  • McDonald, Lucas. "Synthesis and Characterization of Novel Flavonoid-Based Fluorescent Sensors and other Sensors with Excited State Intramolecular Proton Transfer for Biological Applications." Doctoral dissertation, University of Akron, 2018. http://rave.ohiolink.edu/etdc/view?acc_num=akron1524658238472646

    Chicago Manual of Style (17th edition)

akron1524658238472646
516
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This open access ETD is published by University of Akron and OhioLINK.