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Publication Date

2025-5

First Advisor

Maren E. Buck

Second Advisor

Sarah J. Moore

Document Type

Honors Project

Degree Name

Bachelor of Arts

Department

Engineering

Keywords

polymer chemistry, bioengineering, regenerative medicine, drug conjugates, hydrogel scaffolds

Abstract

Polyethylene glycol (PEG) has long been considered the preferred polymer for use in pharmaceutical drugs and biomedical scaffolds. Its highly hydrophilic polyether backbone enhances its solubility in water, making it more biocompatible. However, its simple structure limits the chemistry that can be done with PEG and its derivatives, hence restricting its versatility and use in a wider range of applications. It was also proven to be immunogenic in individuals with pre-existing PEG antibodies, consequently impacting drug efficacy and safety. For these reasons, more versatile and functional polymers are needed for improved outcomes. This thesis project aims to exploit the versatility of an azlactone-based polymer, referred to as poly(2-vinyl-4,4’-dimethyl azlactone) (PVDMA), for applications in targeted drug delivery and tissue engineering. In one aim of this thesis, PVDMA was successfully fabricated for potential applications in targeted drug-delivery. By synthezing the polymer with varying chain lengths and grafting to the engineered protein, Fn3-RGD, protein-polymer conjugates (PPCs) are formed. These particles can bind to ɑv􀀀3 integrin receptors expressed on neovasculature in tumors and on numerous cancer cells, such as on brain cancer cells. The conjugates were successfully formed 24 hours post-conjugation, and the polymer chains could be differentiated with respect to their sizes using size-exclusion chromatography (SEC). The second goal of my thesis sought to develop azlactone-based gels for applications in tissue engineering. PVDMA was crosslinked with Jeffamine-600, another biocompatible polymer, to form hydrogel layers of varying porosity levels. Individual hydrogel layers were characterized through FTIR spectroscopy, swelling analysis, and mechanical testing. The PVDMA-Jeffamine 600 crosslinked gel layers were then superimposed and swelled in solvent to induce differential swelling and force the gel to mimic tubular structures in the body. This design was reiterated multiple times to determine the design’s optimal conditions and maximize its self-rolling behavior. Waiting time between hydrogel casting and 2D aspect ratio were variables found to be particularly relevant, with a waiting time shorter than 1 hour and a 1:2 aspect ratio being the most optimal conditions. RGD peptides were also used to functionalize the inner surface of the tubes to improve cell adhesion, and its hydrophobic nature was found to amplify differential swelling and strengthen self-rolling behavior.

Rights

©2025 Karen Bekhazi. Access limited to the Smith College community and other researchers while on campus. Smith College community members also may access from off-campus using a Smith College log-in. Other off-campus researchers may request a copy through Interlibrary Loan for personal use.

Language

English

Comments

140 pages: color illustrations, charts. Includes bibligraphical references (pages 129-132).

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