Show simple item record

dc.contributor.authorRaczywolski, Zachary
dc.date.accessioned2023-08-10T15:57:31Z
dc.date.available2023-08-10T15:57:31Z
dc.identifier.urihttp://hdl.handle.net/10464/17940
dc.description.abstractThis work outlines the synthesis of three novel silatrane-functionalized lipids and the exploration of their capacity to undergo spontaneous particle formation in aqueous environments. The chemoenzymatic synthesis of the lipids required 1,3-diacylglycerides of octanoyl, lauroyl, and palmitoyl acyl chains to be coupled with 1-(3-aminopropyl)silatrane using 1,1’- carbonyldiimidazole and succinic anhydride. These short, medium, and long-chain models were then subjected to dynamic light scattering analysis after vortexing for 15 minutes in concentrations of 15 mg/mL and 30 mg/mL ultrapure H2O. Previous research has demonstrated that hybrid siloxane phosphocholines that possess a disiloxane moiety appended onto a single tail of many biologically relevant double tail phosphocholines are capable of spontaneously forming vesicles of 100 nm in diameter without the need of extrusion or other forceful techniques at these concentrations. For a direct comparison, the chemoenzymatic synthesis of two medium chain hybrid siloxane phosphocholines and a dynamic light scattering analysis of all six previously studied hybrid siloxane phosphocholines were conducted. At concentrations of 30 mg/mL in ultrapure H2O the six-hybrid siloxane phosphocholines spontaneously formed particles ranging from 97.1 nm to 364.3 nm in diameter, but only the medium chain silatrane derivative formed particles of 200 nm in diameter while the short and long chain silatranyl-lipids required extrusion for particle formation. Attempts were made to further expand the library and synthesize silatranefunctionalized phospholipids using a phosphate to couple the tails to the silatrane rather than succinic anhydride. Despite the various trials, the intermediates were observed to rapidly decompose via 31P NMR, 1H NMR, and TLC, likely due to their hydrolytic instabilityen_US
dc.language.isoengen_US
dc.publisherBrock Universityen_US
dc.rightsCC0 1.0 Universal*
dc.rights.urihttp://creativecommons.org/publicdomain/zero/1.0/*
dc.subjectPhospholipidsen_US
dc.subjectSiliconen_US
dc.subjectSilatranesen_US
dc.subjectDrug-deliveryen_US
dc.titleTHE SYNTHESIS OF SILICON-MODIFIED LIPIDS AND THE INVESTIGATION OF THEIR SURFACE PROPERTIESen_US
dc.typeElectronic Thesis or Dissertationen_US
dc.degree.nameM.Sc. Chemistryen_US
dc.degree.levelMastersen_US
dc.contributor.departmentDepartment of Chemistryen_US
dc.degree.disciplineFaculty of Mathematics and Scienceen_US
refterms.dateFOA2023-08-10T15:57:32Z


Files in this item

Thumbnail
Name:
Zach Raczywolski MSc Thesis ...
Size:
3.589Mb
Format:
PDF

This item appears in the following Collection(s)

Show simple item record

CC0 1.0 Universal
Except where otherwise noted, this item's license is described as CC0 1.0 Universal