Anneli Nina

Date of Award

7-2022

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Biomedical and Chemical Engineering and Sciences

First Advisor

D. Andrew Knight

Second Advisor

Christopher D. Chouinard

Third Advisor

Karen Kim Guisbert

Fourth Advisor

Okhil Nag

Abstract

This work aimed to investigate the degradation of fentanyl in aqueous solutions using unsupported water-soluble cobalt(III) porphyrins (55 and 56), AuNP supported water-soluble cobalt(III) porphyrins (67 and 68), and liposome supported water-soluble cobalt(III) porphyrins (69 and 70). Complexes 55, 56, 68, and 69 have been shown to remove fentanyl from aqueous solutions at 37 ºC. The degradation of fentanyl, and the identification of breakdown products were analyzed with the use of time-of-flight mass spectrometry (TOFMS). Complex 55 has been shown to completely degrade fentanyl at 37 ºC in as little as two hours with a 400 mol% catalyst loading. Complex 56 has been shown to completely degrade fentanyl from aqueous solutions at 37 ºC: within 24 hours at 37 ºC with a catalyst loading of 100 mol%, and in as little as two hours with catalyst loadings of 400 – 500 mol%. One of the most notable products observed was the N-dealkylation of fentanyl at the piperidine ring which resulted in the formation of norfentanyl, a known inactive fentanyl analog.

Complex 68 removed 83% of fentanyl within 24 hours at 37 ºC with a catalyst loading of 100 mol%. However, the AuNP@PEG600 system that did not have a catalyst supported on it was also capable of removing fentanyl, 89% within 24 hours, 37 ºC, and yielded products similar to those seen in the reaction involving 68. Complex 69 removed 16% of fentanyl within 24 hours at 37 ºC with a catalyst loading of 300 mol%. However, control experiments showed that fentanyl interacts with the catalyst free liposome. In summary, complexes 55 and 56 were capable of completely removing fentanyl. The complete removal of fentanyl (< 5% of fentanyl remaining) from aqueous solutions, at a biologically relevant temperature (37 ºC), and within a reasonable amount of time (< 2 hours) was observed.

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