Nanoparticles of gold, silver and other metals coated with lipid bilayers are being researched to target specific cellular targets in vivo by the Reinhard group at BU. In collaboration with the Reinhard group, the Snyder group is investigating the use of triterpenes as multiple drug carriers. The goal of this project is to have the nanoparticle reach its target cells and then release the drugs carried by the triterpene. Betulin is an abundant, naturally-occurring triterpene found in the bark of white birch trees, Betula alba. Both betulin, and its C28 oxidized form betulinic acid, are known to have anti-tumor and anti-HIV activities. Our group has hypothesized that a betulin-derivative has the potential to deliver up to three drugs. To synthesize the desired betulin derivative, the C28 alcohol of betulin was esterified selectively with propiolic acid for the attachment of a drug via Click chemistry. For quantification, a fluorophore will be attached via Click and the hydrolysis of the ester to release this fluorophore will be monitored. The C3 secondary alcohol can be oxidized to the ketone which can then undergo oxime formation with a second drug on the alkoxyamine. The release of the second drug will occur via photoreductive cleavage using the gold nanoparticle and a catalyst as a source of electrons. Additionally the C30 vinyl group of betulin can undergo ozonolysis to yield a ketone which can subsequently undergo oxime formation to attach the third drug, as illustrated in Scheme 1.

Betulin as a multiple drug carrier using 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.