S-Nitroso-N-Acetyl-D-Penicillamine Modified Hyperbranched Polyamidoamine for High-Capacity Nitric Oxide Storage and Release

Synthetic nitric oxide (NO)-donating materials have been shown to have many beneficial effects when incorporated into biomedical materials. When released in the correct dosage, NO has been shown to increase the biocompatibility of blood and tissue contacting materials, but materials are often limited in the amount of NO that can be administered over a period of time. To address this, hyperbranched polyamidoamine (HPAMAM) was modified with the S-nitrosothiol, S-nitroso-N-acetyl-D-penicillamine, and nitrosated to form a controlled, high-capacity NO-donating compound (SNAP-HPAMAM). This compound has the potential of modifying polymers to release NO over long periods of time by being blended into a variety of base polymers. Nitric oxide release was triggered by photoinitiation and through passive ion-mediated release seen under physiological conditions. A material that delivers the beneficial dose of NO over a long period of time would be able to greatly increase the biocompatibility of long-term implantable devices. Structural analysis of a generation 2 HPAMAM molecule was done through Fourier transform infrared spectroscopy (FTIR), H-1 nuclear magnetic resonance spectroscopy (NMR), and matrix assisted laser desorption ionization, time of flight (MALDI-TOF) mass spectrometry. The NO capacity of the finalized generation 2 SNAP-HPAMAM compound was approximately 1.90 +/- 0.116 mu mol NO/mg. Quantification of the functional groups in the compound proved that an average of 6.40 +/- 0.309 reactive primary amine sites were present compared to the 8 reactive sites on a perfectly synthesized generation 2 dendrimer. There is a substantial advantage of using the hyper-branched HPAMAM over purified dendrimers in terms of reduced labor and expense while still providing a high-capacity NO donor that can be blended into different polymer matrices.