Polyhedral Oligomeric Silsesquioxanes (POSS) are a class of nanostructured compounds based on Si-O linkages forming a cage with a silicon atom at each vertex, where substituents are bound tetrahedrally determining the physical and chemical properties of the cage. The vast variety of functional groups that can be added to the cage allows for this class of nanocomposites to be used in a variety of applications such as design of novel materials, bioimaging and drug delivery to name a few. Photosensitizers like porphyrins used in light-activated therapies are hydrophobic molecules leading to self-aggregationin aqueous media, causing decreased bioavailability for biomedical applications. We hypothesize that by using the multifunctionality of POSS platform, we can selectively introduce photosensitizer(s), with targeting and hydrophilic groups for tuning the final properties of the POSS derivatives.The aims for my project are: 1) synthesize porphyrin-based octaaminopropyl-POSS and the trimethylammonium version, and 2) fabricateporphyrin-based bifunctional POSS system containing a targeting group. These novel molecules will be used for the selective elimination of drug resistance bacteria.<br/>The porphyrin octaaminopropyl POSS was synthesized through the condensation of aminopripyltriethoxy-silane followed by conjugation reaction with the 5-[4-(succinimidyloxycarbonyl)phenyl]-10,15,20-triphenylporphyrin. The trimethylammonium version was afforded after full methylation in the presence of methyl iodide. The porphyrin-based POSS derivatives were fully characterized using different techniques including FT-IR, UV-vis, 1H and 29Si NMR, and MALDI-MS. The fluorescence and singlet oxygen quantum yield for those compounds were also determined. These compounds will be tested with different strains of E. coli.

Synthesis of multifunctional porphyrin-based polyhedral oligomeric silsesquioxane molecules for the selective treatment of antibiotic resistant bacteria

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.