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Date Permissions Signed

5-20-2022

Date of Award

Spring 2022

Document Type

Masters Thesis

Department or Program Affiliation

Chemistry

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Murphy, Amanda R.

Second Advisor

Larsen, Michael B.

Third Advisor

Antos, John M.

Abstract

Thiolated polymers, or thiomers, have demonstrated advanced adhesion to biological surfaces such as mucus membranes due to their ability to form disulfide bonds to the cysteine-rich domains in mucin making them an attractive drug delivery system. Silk fibroin, a protein derived from the Bombyx mori silkworm, offers a biocompatible and biodegradable platform absent in other thiomer systems. However, due to the small percentage of native cysteine residues in silk, installation of additional thiols is essential to create an advanced thiomer adhesive. In this research, covalent attachment of non-native thiols to the tyrosine residues of silk fibroin is accomplished with a high degree of functionalization. The extent of thiol modification is characterized by ultraviolet-visible spectroscopy (UV-VIS), proton nuclear magnetic resonance spectroscopy (1H NMR), and 1H-15N heteronuclear multiple bond correlation (HMBC). The reactivity of the thiol handles are probed using fluorescence spectroscopy and the in situ gelling ability of the thiolated silk is investigated using infrared spectroscopy (IR) and rheological measurements.

Type

Text

Keywords

Silk, tyrosine, disulfide, thiol, mucoadhesion, crosslinking, gel

Publisher

Western Washington University

OCLC Number

1319737005

Subject – LCSH

Polymers; Cysteine; Thiols--Synthesis; Silk--Biocompatibility; Silk--Biodegradation

Format

application/pdf

Genre/Form

academic theses

Language

English

Rights

Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.

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