Date of Award

Spring 5-2-2022

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

First Advisor

Dr. Maged Henary

Abstract

This dissertation work focuses primarily on three major biomedical areas; optoacoustic imaging, near infrared fluorescence imaging, and metal sensing bioprobes. The first section describes rational design and synthesis of new aminocyanine bioprobes that selectively highlight pancreatic cancer (PC) tissues with the potential to improve pancreatic ductal adenocarcinoma (PDAC) margin assessment through the selective highlighting of individual PC cells via optoacoustic imaging. Aiming at a better understanding of the factors governing what structural features of a small molecule gives rise to strong optoacoustic signal with unique shape and signal intensity at different pH media, we have reported for the first time unique aminocyanine scaffolds with improved structural features. The second work highlights new bioprobes that showed superior ability to chelate or binding to redox-active metal ions, Cu2+ and Fe3+. The probes exhibited strong sensitivity and selectivity towards their respective ions over other competitive metal ions investigated. The sensors synthesized showed a colorimetric and ratiometric absorption and emission responses. In addition, the probes were able to detect their respective metal ions in real time. The above results show that these probes could be used in real time monitoring of these biologically and environmentally relevant metal ions in various fields. The third section emphasizes on near infrared window I and II fluorescence imaging. Heptamethine fluorophores that absorb and emit within the near infrared window I region have been synthesized efficiently and their biodistribution properties have been investigated. The results indicated that discrete changes in the structural features of the dyes have a pronounced effect on the biodistribution properties of the small bioprobes. In addition, a new class of tetrahydroxanthylium dyes to the best of our knowledge, are the first NIR-II small molecules that have been synthesized using microwave chemistry by our lab. NIR window II fluorescence imaging of these probes resulted in higher uptake in the adrenal gland and micellar structures of the dyes improved the targetability of the original dyes to the bone marrow, lymph nodes, and nerves. Overall, NIR-II imaging has the potential to visualize biologically targeted tissues in the living organisms.

DOI

https://doi.org/10.57709/28913187

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