Date of Award

5-2023

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Biomedical and Chemical Engineering and Sciences

First Advisor

Jessica Smeltz

Second Advisor

Bo Wang

Third Advisor

Rudolf Wehmschulte

Fourth Advisor

Manolis Tomadakis

Abstract

An increase in the misuse of opioids in the United States and the increasing potency of analogs necessitates novel treatments of opioid overdose. The chemical structure of synthetic opioids, such as fentanyl, carfentanil, and morphine possess a trialkyl amine functional group (-NR3) which makes for a promising target for potential catalysts. Iron (III)-tetrasulfonatophenyl porphyrin (complex 9) was synthesized as a potential catalyst for degradation of fentanyl. Complex 9a was prepared from the direct reaction of the free porphyrin and FeSO4. Complex 9b was prepared from the direct reaction of the free porphyrin and FeCl2 in refluxing DMF. The complexes were characterized using UV-vis spectroscopy. We hypothesized that, because the structure of complex 9 is similar to that of cytochrome P450, an enzyme found in the liver, complex 9 would be capable of catalytically degrading fentanyl. The catalytic activity of complex 9 was assessed in aqueous conditions at 37C with varying concentration of fentanyl and the removal of fentanyl was determined using high resolution mass spectrometry. Complex 9a was found to remove 30.75% of fentanyl from solution after 72 hours with a catalyst to substrate ratio of 5:1. Most notably, a breakdown product observed following this reaction is norfentanyl, an inactive fentanyl analog that is formed via the N-dealkylation of fentanyl at the piperidine ring. Complex 9b was found to remove 96.71% of fentanyl from solution after 72 hours with a catalyst to substrate ratio of 5:1. No breakdown products were observed for this reaction.

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