Nitric oxide releasing polyurethanes with covalently linked diazeniumdiolated secondary amines

Biomacromolecules
Melissa M ReynoldsMark E Meyerhoff

Abstract

Two novel strategies for synthesizing stable polyurethanes (PUs) capable of generating bioactive nitric oxide (NO) are described. The methods rely on covalently attaching diazeniumdiolate (N(2)O(2)(-)) groups onto secondary amine nitrogens at various positions within the polymer chain such that, when in contact with water or physiological fluids, only the two molecules of NO available from each diazeniumdiolate moiety are released into the surrounding medium, with potential byproducts remaining covalently bound to the matrix. Extensive analysis of the NO(x)() products released from the polymers was employed to develop appropriate strategies to better stabilize the diazeniumdiolate-based polymer structures. In one approach, diazeniumdiolate groups are attached to secondary amino nitrogens of alkane diamines inserted within the diol chain extender of a PU material. Oxidative loss of NO was minimized by blending the polymer with a biocompatible, relatively nonnucleophilic salt before exposing solutions of the polymer to NO during the diazeniumdiolation step. Fluxes of molecular NO from such materials during immersion in physiological buffer reached levels as high as 19 pmol x cm(-2) x s(-1) with a total recovery of 21 nmol of NO/m...Continue Reading

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Citations

Jan 22, 2011·ACS Applied Materials & Interfaces·Peter N ConeskiMark H Schoenfisch
Jun 6, 2012·ACS Applied Materials & Interfaces·Kathryn A WoldMelissa M Reynolds
Jan 24, 2012·Journal of the American Chemical Society·Jacqueline L Harding, Melissa M Reynolds
Aug 20, 2008·Langmuir : the ACS Journal of Surfaces and Colloids·Jun YangMark E Meyerhoff
Mar 1, 2012·Chemical Society Reviews·Daniel A Riccio, Mark H Schoenfisch
Dec 19, 2009·Regenerative Medicine·Swathi Ravi, Elliot L Chaikof
Dec 7, 2010·Journal of Materials Chemistry·Melissa M ReynoldsMark E Meyerhoff
Jan 1, 2015·International Journal of Molecular Sciences·Ee Teng GohAlexander M Seifalian
Dec 22, 2015·Journal of Controlled Release : Official Journal of the Controlled Release Society·Adoracion Pegalajar-JuradoMelissa M Reynolds
Mar 18, 2008·Bioorganic & Medicinal Chemistry Letters·Yuxia Kou, Ajun Wan
Sep 17, 2015·Journal of Controlled Release : Official Journal of the Controlled Release Society·Adoracion Pegalajar-JuradoMelissa M Reynolds
May 7, 2008·Angewandte Chemie·Russell E Morris, Paul S Wheatley
Nov 9, 2012·Small·Noora NaghaviAlexander M Seifalian
Jan 25, 2012·Advanced Functional Materials·Michele C JenGuillermo A Ameer
Jul 2, 2009·Journal of Biomedical Materials Research. Part a·Haichao ZhaoGuillermo A Ameer
Feb 9, 2016·Future Science OA·Hongying LiangJoel M Friedman
Oct 8, 2016·Journal of Biomaterials Science. Polymer Edition·John Eric JonesMeng Chen
Nov 4, 2016·Journal of Biomedical Materials Research. Part a·Marcus J GoudieHitesh Handa
Sep 19, 2008·Vascular and Endovascular Surgery·Vinit N VaruMelina R Kibbe
Apr 9, 2008·Circulation·Muneera R KapadiaMelina R Kibbe
May 26, 2017·American Journal of Cardiovascular Drugs : Drugs, Devices, and Other Interventions·Gail M AnnichMelissa M Reynolds
Feb 7, 2017·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Hao GuHong Chen
Jan 28, 2014·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Jihoon KimWon Jong Kim
Nov 14, 2014·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Alec LutzkeMelissa M Reynolds
Sep 9, 2018·Biointerphases·Yanyi ZangMelissa M Reynolds
Dec 28, 2015·Journal of Materials Chemistry. B, Materials for Biology and Medicine·J P YaporM M Reynolds
Oct 4, 2008·Biomacromolecules·Achala de MelAlexander M Seifalian
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Nov 29, 2017·ACS Applied Materials & Interfaces·Rana R HaikalMohamed H Alkordi
Apr 10, 2020·ACS Applied Materials & Interfaces·Ryan DevineHitesh Handa

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