In collaboration with the Reinhard group, we are investigating the adaptation of isosteviol, as a multiple drug carrier. The Reinhard group focuses on gold and silver nanoparticles coated with lipid bilayers that can target HIV particles in vivo. Stability of the bilayers depends on the presence of cholesterol, and preliminary results indicate that a significant amount of cholesterol can be replaced with isosteviol derivatives. An isosteviol iodo-oxime was synthesized, and 40 mol% cholesterol replacement was integrated into the bilayer. This oxime was synthesized by forming the iodobenzyl-alkoxyamine, which was then used in the oxime reaction. This oxime can be used to follow the movement of the molecule into the bilayer by ICP-MS, and can be used to quantify bond breaking that can occur in the bilayer. This bond breaking can be used to deliver drugs, if the oxime is replaced by a drug substrate. The carboxylic acid of isosteviol has also been coupled to an alkyne via an S<sub>N</sub>2 reaction, so that click chemistry can be used to “click” on a drug. This gives isosteviol a second drug carrier site that can be utilized. We have taken preliminary steps to prove that nanoparticles are a feasible drug delivery system with molecules that can carry more than one drug, both showing that the molecules can be incorporated into the bilayer and showing that there are transformations at multiple sites that could be used to attach a drug to the molecule.

Development of isosteviol as a multiple drug carrier via nanoparticles

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.