More Lipophilic Dialkyldiamine-Based Diazeniumdiolates: Synthesis, Characterization, and Application in Preparing Thromboresistant Nitric Oxide Release Polymeric Coatings
Abstract
The synthesis, characterization, and biomedical application in preparing more thromboresistant polymeric coatings for a series of lipophilic dialkyldiamine-based diazeniumdiolatesare described. Dialkylhexamethylenediamine diazeniumdiolates of the form RN[N(O)NO](-)(CH(2))(6)NH(2)(+)R, where R = CH(3), CH(2)CH(3), (CH(2))(2)CH(3), (CH(2))(3)CH(3), (CH(2))(4)CH(3,) (CH(2))(5)CH(3), and (CH(2))(11)CH(3), are prepared via reaction of the corresponding diamine with NO. The more lipophilic diazeniumdiolates [e.g., R = (CH(2))(3)CH(3)] can be incorporated into hydrophobic polymeric films (e.g., plasticized PVC), and the resulting materials release NO for extended periods of time upon exposure to PBS buffer. The mechanism of NO release from these films is examined in detail. More stable initial NO release can be achieved by adding lipophilic anionic species (e.g., tetraphenylborate derivative) to the polymeric material to buffer the activity of protons within the organic phase. It is shown that the use of these new lipophilic NO-donors in polymers provides the ability to tailor NO release rates for a variety of medical applications. As an example, polymers doped with N,N'-dibutylhexamethylenediamine diazeniumdiolate and a tetraphenylborate derivative are employed as coatings for vascular grafts in sheep. The NO release grafts exhibited enhanced performance and had an average 95% thrombus-free surface area compared to 42% for the corresponding control grafts when examined after 21d of implantation.
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Batchelor et al. synthesized more lipophilic NONOates to reduce leaching of NO donors into blood from doped polymers.
“Batchelor et al. synthesized more lipophilic NONOates for use in reducing the NO donor leaching into blood from polymers that had been doped with such NO donors.153”
From Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO) (2016) · cites this paper as [153]
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- Authors
- Batchelor, M. M., Reoma, S. L., Fleser, P. S., Nuthakki, V. K., Callahan, R. E., Shanley, C. J., Politis, J. K., Elmore, J., Merz, S. I., & Meyerhoff, M. E.
- Affiliations
- University of Michigan (US)
- Corresponding author
- Meyerhoff, Mark E.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-10-29
- Volume
- 46
- Issue
- 24
- Pages
- 5153-5161
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2016855997
- Cited by
- 120
- References
- 17
- Citations by year
- 2025: 3 · 2023: 3 · 2022: 3 · 2021: 3 · 2020: 5 · 2019: 4 · 2018: 2 · 2017: 4 · 2016: 9 · 2015: 8 · 2014: 10 · 2013: 11 · 2012: 5
- FWCI
- 4.40
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Medicinal Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Institute of Biomedical Imaging and Bioengineering (EB 00783, R01EB000783)
- Topics
- Health Sciences › Medicine › Physiology › Nitric Oxide and Endothelin Effects
- Physical Sciences › Materials Science › Surfaces, Coatings and Films › Polymer Surface Interaction Studies
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmaceutical Science › Advanced Drug Delivery Systems
- Keywords
- diazeniumdiolates, hexamethylenediamine, nitric oxide release, polymer coatings, thromboresistance, vascular grafts, tetraphenylborate, thrombus formation
- MeSH terms
- Animals, Azo Compounds, Blood Vessel Prosthesis, Borates, Diamines, Drug Carriers, Drug Stability, Hydrogen-Ion Concentration, Kinetics, Luminescent Measurements, Nitric Oxide, Polymers, Polyurethanes, Sheep, Siloxanes, Structure-Activity Relationship, Thrombosis, Nitric Oxide Donors, Hydrophobic and Hydrophilic Interactions
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