Synthesis of novel N-diazeniumdiolates based on hyperbranched polyethers

Kou, Yuxia; Wan, Ajun

doi:10.1016/j.bmcl.2008.02.073

Cited by 5 publications

(7 citation statements)

References 19 publications

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“…238 Briefly, the diaminoalkyltrimethoxysilane (DACA) was reacted with the terminal hydroxyl groups of the PDMS, and then the aminated PDMS macromolecules were cross-linked to each other (condensation-curing) in the presence of ambient moisture before forming the NONOates species at the amine sites (via reaction of the polymer with NO (g) at high pressure). Likewise, N -diazeniumdiolated NO donors have been covalently linked to polyester, 240 polymethacrylate, 223 polyurethane (PU), 35,110,233,234 PVA 232 and other hydrogels 241 as well. The synthetic methods are somewhat similar to that described above, with the exception of one type of PU containing a diamine chain extender, where sodium salts (NaX, where X is an anion) are incorporated into the reaction mixture during the NO addition process to facilitate the formation of anionic diazeniumdiolates.…”

Section: Polymer-based Strategies For No Deliverymentioning

confidence: 99%

“…RSNOs have also been used to form functionalized dendrimers 213 or hyperbranched polymers (e.g., hyperbranched polyamidoamine (HPAMAM) or hyperbranched polyethers 240 ) to achieve a high NO payload. Stasko et al functionalized generation 4 polyamidoamine (PAMAM) dendrimers with N-acetylpenicillamine or N-acetylcysteine and both macromolecular scaffolds have an NO storage of ca.…”

Section: Polymer-based Strategies For No Deliverymentioning

confidence: 99%

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Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO)

et al. 2016

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Biomedical devices are essential for patient diagnosis and treatment; however, when blood comes in contact with foreign surfaces or homeostasis is disrupted, complications including thrombus formation and bacterial infections can interrupt device functionality, causing false readings and/or shorten device lifetime. Here, we review some of the current approaches for developing antithrombotic and antibacterial materials for biomedical applications. Special emphasis is given to materials that release or generate low levels of nitric oxide (NO). Nitric oxide is an endogenous gas molecule that can inhibit platelet activation as well as bacterial proliferation and adhesion. Various NO delivery vehicles have been developed to improve NO’s therapeutic potential. In this review, we provide a summary of the NO releasing and NO generating polymeric materials developed to date, with a focus on the chemistry of different NO donors, the polymer preparation processes, and in vitro and in vivo applications of the two most promising types of NO donors studied thus far, N-diazeniumdiolates (NONOates) and S-nitrosothiols (RSNOs).

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Section: Polymer-based Strategies For No Deliverymentioning

confidence: 99%

Section: Polymer-based Strategies For No Deliverymentioning

confidence: 99%

Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO)

et al. 2016

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“…This vehicle can store up to 2 μmol NO/mg dendrimer, and releases NO when triggered with copper (II) or light. Other examples of PAMAM dendrimers functionalized with NO donors groups ( S -nitrosothiols, N -acetylpenicillamine and N -acetylcysteine) have been described [ 153 , 154 ].…”

Section: Biomedical Applicationsmentioning

confidence: 99%

New Advances in General Biomedical Applications of PAMAM Dendrimers

et al. 2018

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Dendrimers are nanoscopic compounds, which are monodispersed, and they are generally considered as homogeneous. PAMAM (polyamidoamine) was introduced in 1985, by Donald A. Tomalia, as a new class of polymers, named ‘starburst polymers’. This important contribution of Professor Tomalia opened a new research field involving nanotechnological approaches. From then on, many groups have been using PAMAM for diverse applications in many areas, including biomedical applications. The possibility of either linking drugs and bioactive compounds, or entrapping them into the dendrimer frame can improve many relevant biological properties, such as bioavailability, solubility, and selectivity. Directing groups to reach selective delivery in a specific organ is one of the advanced applications of PAMAM. In this review, structural and safety aspects of PAMAM and its derivatives are discussed, and some relevant applications are briefly presented. Emphasis has been given to gene delivery and targeting drugs, as advanced delivery systems using PAMAM and an incentive for its use on neglected diseases are briefly mentioned.

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“…NO-releasing hyperbranched polyethers have been previously synthesized incorporating N-diazeniumdiolate NO donors, but have shown poor NO addition efficiency, obtaining a surprisingly small NO reservoir of 0.43 µmol/mg [21]. N-diazeniumdiolate molecules also do not have the controllability in NO release seen with SNAP based NO donors as its release mechanism is triggered when put in physiological pH and temperature [22].…”

Section: Introductionmentioning

confidence: 99%

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

Hopkins

Frost

2020

Bioengineering

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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), 1H 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 µmol 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.

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Synthesis of novel N-diazeniumdiolates based on hyperbranched polyethers

Cited by 5 publications

References 19 publications

Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO)

Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO)

New Advances in General Biomedical Applications of PAMAM Dendrimers

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

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