Covalent Conjugation of 2-Hydroxyethylmethacrylate with an Anti-Biofouling 2-Aminoimidazole Small Molecule and its Effect on an Experimental Dental Adhesive
Author
Hampton, Joey R
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Abstract
Secondary caries, or cavities that have re-infected previously restored teeth, are a
prevalent problem in the oral health community. An overwhelming 74% of restored teeth require
further work and replacement restorations; many of which are due to patient’s lack of oral
hygiene and knowledge.1 Often, the initial carious tissue is due to lack of oral hygiene and after
procedural restorations, no changes occur in their daily routine. This certainly contributes to the
replacement rate; however, the remaining portion is due to the lack of preventative measures in
the current methacrylate resin composite materials clinically utilized. Thus, there is a critical
need to produce a dental adhesive with preventative characteristics. Which can reduce the high rate replacement for such materials.
To create such a dental adhesive, a 2-aminoimidazole (2-AI) motif derived from sea
sponges that has shown capabilities of disrupting bacterial biofilms has been chemically
conjugated to 2-hydroxyethyl methacrylate (HEMA, 1), a methacrylate commonly used in dental
adhesives. Briefly, boc-protected 2-aminoimidazole (8) was coupled to a commercially available
alkyne using standard conditions of amide formations. In the key step of the synthesis, the alkyne
(9) was subjected to a “click” reaction with the known azide (3) and pushed through HPLC for
separation. Under the pressure of HPLC and the presence of TFA, the product was deprotected
and the final product was prematurely synthesized. At this stage, the solid functionalized
methacrylate product (10), was incorporated into a control group polymer blend to produce an
experimental dental adhesive.
When co-polymerized at 1mM concentration, no significant differences in the mechanical
properties were determined between control, commercial and experimental groups. The polymer
also displayed similar degrees of conversion amongst groups and were slightly increased
compared to literature values of the commercial adhesive Clearfil SE Protect. Additionally, the
new monomer showcased anti-biofouling properties, however, when incorporated at 10 mM
concentration into the polymer blend, no bacterial depletion was noted.
Subject
Date
2023-06-22
Citation:
APA:
Hampton, Joey R.
(June 2023).
Covalent Conjugation of 2-Hydroxyethylmethacrylate with an Anti-Biofouling 2-Aminoimidazole Small Molecule and its Effect on an Experimental Dental Adhesive
(Master's Thesis, East Carolina University). Retrieved from the Scholarship.
(http://hdl.handle.net/10342/13158.)
MLA:
Hampton, Joey R.
Covalent Conjugation of 2-Hydroxyethylmethacrylate with an Anti-Biofouling 2-Aminoimidazole Small Molecule and its Effect on an Experimental Dental Adhesive.
Master's Thesis. East Carolina University,
June 2023. The Scholarship.
http://hdl.handle.net/10342/13158.
May 15, 2024.
Chicago:
Hampton, Joey R,
“Covalent Conjugation of 2-Hydroxyethylmethacrylate with an Anti-Biofouling 2-Aminoimidazole Small Molecule and its Effect on an Experimental Dental Adhesive”
(Master's Thesis., East Carolina University,
June 2023).
AMA:
Hampton, Joey R.
Covalent Conjugation of 2-Hydroxyethylmethacrylate with an Anti-Biofouling 2-Aminoimidazole Small Molecule and its Effect on an Experimental Dental Adhesive
[Master's Thesis]. Greenville, NC: East Carolina University;
June 2023.
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Publisher
East Carolina University