Skip to main content
Erschienen in: Polymer Bulletin 7/2018

03.10.2017 | Original Paper

Non-enzymatic nitric oxide release from biodegradable S-nitrosothiol bound polymer: synthesis, characterization, and antibacterial effect

verfasst von: S. Sundari, Sheela Berchmans, S. Umadevi

Erschienen in: Polymer Bulletin | Ausgabe 7/2018

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Nitric oxide (NO) delivery is an effective method for the development of NO-mediated therapy under the physiological conditions for biological applications. S-nitrosothiol is the most widely used NO donor for therapeutics which is capable of spontaneously releasing NO under physiological conditions and acts as a potential stable source of NO and as an S-nitrosating agent. In this present work, the preparation of a biodegradable and biocompatible polymer poly(acrylic acid) (PAA–CANO) cross linked with the S-nitrosothiol,cysteamine (CANO) is reported. Thus, prepared polymer showed a controlled maximum release of NO up to 6 days and it provided a potential defense against pathogenic bacteria. The prepared PAA–CANO was characterized by various techniques such as Fourier transform infrared spectroscopy, ultraviolet–visible spectrophotometry, nuclear magnetic resonance spectroscopy, and thermogravimetric analysis. In addition, loading of PAA–CANO into spongy scaffolds consisting of chitosan and alginate in 1:2 ratio resulting in a new antibacterial active compound suitable for providing infection-free environment on surgical covers, devices, and apparel is also reported. This polymeric scaffold showed a controlled NO release of 2.43 × 10−10 M/s/cm2. The morphology of the scaffolds is a micro-fibrous structure with a porosity of 57% and it was characterized by scanning electron microscopy.

Graphical abstract

Covalent tethering of nitric-oxide-releasing compound S-nitrosocysteamine to poly(acrylic acid) improves its stability and leads to controlled release of nitric oxide useful for the antibacterial activity.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
8.
Zurück zum Zitat Hrabie Ja, Keefer LK (2002) Chemistry of the nitric oxide-releasing diazeniumdiolate “(nitrosohydroxylamine)” functional group and its oxygen-substituted derivatives. Chem Rev 102:1135–1154. doi:10.1021/cr000028t CrossRefPubMed Hrabie Ja, Keefer LK (2002) Chemistry of the nitric oxide-releasing diazeniumdiolate “(nitrosohydroxylamine)” functional group and its oxygen-substituted derivatives. Chem Rev 102:1135–1154. doi:10.​1021/​cr000028t CrossRefPubMed
10.
Zurück zum Zitat Duong HTT, Kamarudin ZM, Erlich RB et al (2013) Intracellular nitric oxide delivery from stable NO-polymeric nanoparticle carriers. Chem Commun (Camb) 49:4190–4192. doi:10.1039/c2cc37181b CrossRef Duong HTT, Kamarudin ZM, Erlich RB et al (2013) Intracellular nitric oxide delivery from stable NO-polymeric nanoparticle carriers. Chem Commun (Camb) 49:4190–4192. doi:10.​1039/​c2cc37181b CrossRef
26.
Zurück zum Zitat Lutzke A, Pegalajar-Jurado A, Neufeld BH, Reynolds MM (2014) Nitric oxide-releasing S-nitrosated derivatives of chitin and chitosan for biomedical applications. J Mater Chem B 2:7449–7458. doi:10.1039/C4TB01340A CrossRef Lutzke A, Pegalajar-Jurado A, Neufeld BH, Reynolds MM (2014) Nitric oxide-releasing S-nitrosated derivatives of chitin and chitosan for biomedical applications. J Mater Chem B 2:7449–7458. doi:10.​1039/​C4TB01340A CrossRef
27.
Zurück zum Zitat Damodaran VB, Joslin JM, Wold Ka et al (2012) S-nitrosated biodegradable polymers for biomedical applications: synthesis, characterization and impact of thiol structure on the physicochemical properties. J Mater Chem 22:5990. doi:10.1039/c2jm16554f CrossRef Damodaran VB, Joslin JM, Wold Ka et al (2012) S-nitrosated biodegradable polymers for biomedical applications: synthesis, characterization and impact of thiol structure on the physicochemical properties. J Mater Chem 22:5990. doi:10.​1039/​c2jm16554f CrossRef
28.
30.
Zurück zum Zitat Joslin JM, Lantvit SM, Reynolds MM (2013) Nitric oxide releasing tygon materials: studies in donor leaching and localized nitric oxide release at a polymer-buffer interface. ACS Appl Mater Interfaces 5:9285–9294. doi:10.1021/am402112y CrossRefPubMed Joslin JM, Lantvit SM, Reynolds MM (2013) Nitric oxide releasing tygon materials: studies in donor leaching and localized nitric oxide release at a polymer-buffer interface. ACS Appl Mater Interfaces 5:9285–9294. doi:10.​1021/​am402112y CrossRefPubMed
33.
Zurück zum Zitat Tiyaboonchai W (2003) Chitosan nanoparticles: a promising system for drug delivery. Naresuan Univ J 11:51–66 Tiyaboonchai W (2003) Chitosan nanoparticles: a promising system for drug delivery. Naresuan Univ J 11:51–66
36.
Zurück zum Zitat Kayaman-Apohan N, Akdemir ZS (2005) Synthesis and characterization of pendant carboxylic acid functional poly(lactic acid) and poly(lactic acid-co-glycolic acid) and their drug release behaviors. Polym Adv Technol 16:807–812. doi:10.1002/pat.656 CrossRef Kayaman-Apohan N, Akdemir ZS (2005) Synthesis and characterization of pendant carboxylic acid functional poly(lactic acid) and poly(lactic acid-co-glycolic acid) and their drug release behaviors. Polym Adv Technol 16:807–812. doi:10.​1002/​pat.​656 CrossRef
38.
Zurück zum Zitat Morakinyo MK, Chipinda I, Hettick J et al (2012) Detailed mechanistic investigation into the S-nitrosation of cysteamine. Can J Chem 90:724–738. doi:10.1139/v2012-051 CrossRef Morakinyo MK, Chipinda I, Hettick J et al (2012) Detailed mechanistic investigation into the S-nitrosation of cysteamine. Can J Chem 90:724–738. doi:10.​1139/​v2012-051 CrossRef
39.
Zurück zum Zitat Roy B, Moulinet A, Fontecave M (2016) New thionitrites: synthesis, stability. J Org Chem 59(23):7019–7026CrossRef Roy B, Moulinet A, Fontecave M (2016) New thionitrites: synthesis, stability. J Org Chem 59(23):7019–7026CrossRef
40.
44.
Zurück zum Zitat Zeng M, Feng Z, Huang Y et al (2016) Chemical structure and remarkably enhanced mechanical properties of chitosan-graft-poly(acrylic acid)/polyacrylamide double-network hydrogels. Polym Bull. doi:10.1007/s00289-016-1697-0 CrossRef Zeng M, Feng Z, Huang Y et al (2016) Chemical structure and remarkably enhanced mechanical properties of chitosan-graft-poly(acrylic acid)/polyacrylamide double-network hydrogels. Polym Bull. doi:10.​1007/​s00289-016-1697-0 CrossRef
45.
Zurück zum Zitat Zhang XZ, Tian FJ, Hou YM, Ou ZH (2015) Preparation and in vitro in vivo characterization of polyelectrolyte alginate–chitosan complex based microspheres loaded with verapamil hydrochloride for improved oral drug delivery. J Incl Phenom Macrocycl Chem 81:429–440. doi:10.1007/s10847-014-0471-x CrossRef Zhang XZ, Tian FJ, Hou YM, Ou ZH (2015) Preparation and in vitro in vivo characterization of polyelectrolyte alginate–chitosan complex based microspheres loaded with verapamil hydrochloride for improved oral drug delivery. J Incl Phenom Macrocycl Chem 81:429–440. doi:10.​1007/​s10847-014-0471-x CrossRef
46.
Zurück zum Zitat Hemalatha T, Yadav S, Krithiga G, Sastry TP (2016) Chitosan as a matrix for grafting methyl methacrylate: synthesis, characterization and evaluation of grafts for biomedical applications. Polym Bull 73:3105–3117. doi:10.1007/s00289-016-1644-0 CrossRef Hemalatha T, Yadav S, Krithiga G, Sastry TP (2016) Chitosan as a matrix for grafting methyl methacrylate: synthesis, characterization and evaluation of grafts for biomedical applications. Polym Bull 73:3105–3117. doi:10.​1007/​s00289-016-1644-0 CrossRef
Metadaten
Titel
Non-enzymatic nitric oxide release from biodegradable S-nitrosothiol bound polymer: synthesis, characterization, and antibacterial effect
verfasst von
S. Sundari
Sheela Berchmans
S. Umadevi
Publikationsdatum
03.10.2017
Verlag
Springer Berlin Heidelberg
Erschienen in
Polymer Bulletin / Ausgabe 7/2018
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-017-2199-4

Weitere Artikel der Ausgabe 7/2018

Polymer Bulletin 7/2018 Zur Ausgabe

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.