THE SYNTHESIS OF SILICON-MODIFIED LIPIDS AND THE INVESTIGATION OF THEIR SURFACE PROPERTIES

This 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 instability

Name thesis:degree_name

M.Sc. Chemistry

Level thesis:degree_level

Masters

Discipline thesis:degree_discipline

Faculty of Mathematics and Science

Department dc:contributor.department

Department of Chemistry

Grantor

Brock University

Year dc:date.issued

2023

Author dc:creator

• Raczywolski, Zachary

• Phospholipids
• Silicon
• Silatranes
• Drug-delivery

Statement dc:rights

• CC0 1.0 Universal

Licence dc:rights.uri

• http://creativecommons.org/publicdomain/zero/1.0/

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/10464/17940

OAI identifier oai:identifier

oai:brocku.scholaris.ca:10464/17940