Author Type

Graduate Student

Date of Award

Summer 6-5-2026

Document Type

Dissertation

Publication Status

Version of Record

Submission Date

July 2026

Department

Chemistry and Biochemistry

College Granting Degree

Charles E. Schmidt College of Science

Department Granting Degree

Chemistry and Biochemistry

Degree Name

Doctor of Philosophy (PhD)

Thesis/Dissertation Advisor [Chair]

Charles Carraher

Abstract

This research focuses on the synthesis and structural characterization of polymers with anticipated anticancer and antiviral properties by combining metal-containing Lewis acids, organotin dichlorides (R2SnCl2), Group 4 metallocene dichlorides (Cp2TiCl2, Cp2ZrCl2 and Cp2HfCl2), and triphenyl Group 15 metal dichlorides (Ph3AsCl2, Ph3SbCl2 and Ph3BiCl2), with biologically active Lewis bases, lamivudine, a synthetic nucleoside, and camphoric acid, a dicarboxylic acid, to achieve synergistic effect.

Five classes of polymers were synthesized using interfacial polymerization: lamivudine and organotin dichlorides, lamivudine and Group 4 metallocene dichlorides, camphoric acid and triphenyl Group 15 metal dichlorides, camphoric acid and organotin dichlorides, and camphoric acid and Group 4 metallocene dichlorides. The polymers were characterized by infrared spectroscopy (IR), nuclear magnetic resonance (NMR), light scattering (LS) and matrix-assisted laser desorption ionization mass spectrometry (MALDI-MS), which confirmed molecular structures, functional groups, and chain lengths consistent with polymer formation.

The polymers were evaluated for both anticancer and antiviral activity. The anticancer activity was quantified as concentration required to reduce cell viability by 50% (EC50) against six cancer cell lines, and as the ratio of the EC50 for the healthy cell line NIH/3T3 or WI-38 cells divided by the EC50 for the test cell line (CI50). Antiviral activity was evaluated based on the cytopathic effect (CPE) by measuring the minimum inhibitory concentration (MIC), defined as the lowest concentration that provided 100% protection against viral damage.

Camphoric acid metallocene polymers showed significant cytotoxicity with EC50 values in the range of 1.1–1.8 ng/mL, all lower than cisplatin 2.3-5.7 ng/mL for PC-3, MDAMB-231, HT-29 and MCF-7 cell lines. When comparing monomers to their corresponding polymers the CI50 values for polymers were 10-450 times higher. Camphoric acid organotin polymers showed strongest antiviral effects, providing 100% inhibition of Zika strain 502 in Vero cells at a MIC of 0.3 ng/mL, which is significantly more effective than MIC of 16.4 μg/mL for Sofosbuvir, FDA approved drug used as a benchmark for Zika studies. Overall, the cytotoxicity and CPE inhibition results indicate that the biological properties of the polymers are strongly influenced by the metal centers, the organic monomer (lamivudine and camphoric acid), and R-groups on the metal.

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