First Advisor

Lei G. Wang

Date of Award

Spring 6-16-2025

Document Type

Thesis

Degree Name

Bachelor of Science (B.S.) in Chemistry and University Honors

Department

Chemistry

Language

English

Subjects

Prostate Cancer, Fluorescence-Guided Surgery, Targeted Probes, PSMA, EuK

DOI

10.15760/honors.1672

Abstract

Prostate cancer (PCa) is a leading cause of cancer and cancer deaths in men. Radical prostatectomy is the leading treatment, but due to difficulties in maintaining negative surgical margins that are critical for ensuring complete cancer removal, prostatectomies are associated with cancer recurrence. Fluorescence-guided surgery (FGS) has shown promise in reducing the incidence of positive surgical margins through the use of targeted fluorescent probes that visually delineate otherwise ambiguous cancerous tissues. This work aims to produce two targeted near-infrared (NIR) probes viable for PCa imaging and FGS-assisted resection. Methods: Two pentamethine cyanine dyes conjugated with the PSMA (prostate-specific membrane antigen) targeting vector EuK (glutamate-urea-lysine) were synthesized and characterized. Structural and purity characterization were completed using liquid chromatography-mass spectrometry (LC-MS), nuclear magnetic resonance (NMR), and high performance liquid chromatography (HP-LC). For in vitro characterization, several PCa cell lines exhibiting different levels of PSMA expression were cultured, stained, and imaged via fluorescence microscopy. Results: Molecular docking studies supported the probe design, with each probe having docking scores of -13.4 kcal/mol. The probes shared an excitation lambda maximum at 644 nm and an emission lambda maximum at 664 nm. Moreover, the probes possessed high molar extinction coefficients and adequate quantum yields. The in vitro studies demonstrated that each probe had strong specificity for PSMA. Conclusion: Each probe displayed suitable optical properties and excellent affinity towards PSMA-expressing PCa cells. These results support the viability of EuK-conjugated Sulfo-Cy5 dyes as NIR probes for cancer-specific imaging and FGS-assisted prostatectomies.

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Persistent Identifier

https://archives.pdx.edu/ds/psu/43753

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