In recent years nanomaterials have been studied in efforts to design a potential platform for cancer treatment as drug delivery agents. Polyamidoamine (PAMAM) dendrimers are a class of nanomaterials that are star-branched macromolecules containing internal tertiary amines, amide bonds, and terminal primary amines. Conjugation of small molecules to the dendrimer results in nanomaterials that are suitable for treating cancer with greater selectivity and efficacy. Dendrimers conjugated to targeting agents, such as peptides, dyes, and anti-cancer drugs have been used to track and selectively deliver chemotherapeutic agents to cancerous tumor cells. However, due to the high number of conjugation sites, the conjugated dendrimer product results in a distribution of populations varying in the ratio of small molecules per dendrimer including a non-functionalized population. Conjugating first a polar ligand with unique chemistry to the dendrimer would allow for easy separation of the populations with precisely defined numbers of ligands. In this work, generation 5 (G5) PAMAM dendrimers were conjugated with 3-(4-(2-azidoethoxy)phenyl)propanoic acid and 3-(4-(prop-2-ynyloxy)phenyl)propanoic acid as “click chemistry” ligands. The individual populations are able to be separated by rp-HPLC in order to produce nanomaterials with precisely defined numbers of ligands. Subsequently, biomolecules, such as a peptide, could then be conjugated stochastically resulting in a material with a defined number of peptides per dendrimer. Once conjugated, the G5-ligand products were characterized by HPLC, Proton NMR, and Matrix Assisted Laser Desorption Ionization-TOF.<br/>

Synthesizing dendrimer-ligand conjugates for peptide mediated cellular delivery systems

249th National Meeting (2015)

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