Low-molecular-weight sulfonated chitosan as template for anticoagulant nanoparticles

Katja Heise,1,2 Mathias Hobisch,3,4 Liviu Sacarescu,5 Uros Maver,6 Josefine Hobisch,3 Tobias Reichelt,7 Marija Sega,6 Steffen Fischer,1 Stefan Spirk3,4 Members of EPNOE and NAWI Graz 1Institute of Plant and Wood Chemistry, Technische Universität Dresden, Tharandt, Germany; 2Department of...

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Autores principales:	Heise K, Hobisch M, Sacarescu L, Maver U, Hobisch J, Reichelt T, Sega M, Fischer S, Spirk S
Formato:	article
Lenguaje:	EN
Publicado:	Dove Medical Press 2018
Materias:	chitosan ethylsulfonate silver nanoparticles antithrombotic activity cofactor Xa Medicine (General) R5-920
Acceso en línea:	https://doaj.org/article/2315fc8251524d369b30ff280bdc9575
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spelling	oai:doaj.org-article:2315fc8251524d369b30ff280bdc95752021-12-02T06:06:47ZLow-molecular-weight sulfonated chitosan as template for anticoagulant nanoparticles1178-2013https://doaj.org/article/2315fc8251524d369b30ff280bdc95752018-08-01T00:00:00Zhttps://www.dovepress.com/low-molecular-weight-sulfonated-chitosan-as-template-for-anticoagulant-peer-reviewed-article-IJNhttps://doaj.org/toc/1178-2013Katja Heise,1,2 Mathias Hobisch,3,4 Liviu Sacarescu,5 Uros Maver,6 Josefine Hobisch,3 Tobias Reichelt,7 Marija Sega,6 Steffen Fischer,1 Stefan Spirk3,4 Members of EPNOE and NAWI Graz 1Institute of Plant and Wood Chemistry, Technische Universität Dresden, Tharandt, Germany; 2Department of Bioproducts and Biosystems, Aalto University, Espoo, Finland; 3Institute for Chemistry and Technology of Materials, Graz University of Technology, Graz, Austria; 4Institute for Paper, Pulp and Fiber Technology, Graz University of Technology, Graz, Austria; 5“Petru Poni” Institute of Macromolecular Chemistry, Romanian Academy, Iasi, Romania; 6Faculty of Medicine, University of Maribor, Maribor, Slovenia; 7Zentrum für Bucherhaltung GmbH, Leipzig, Germany Purpose: In this work, low-molecular-weight sulfoethyl chitosan (SECS) was used as a model template for the generation of silver core-shell nanoparticles with high potential as anticoagulants for medical applications. Materials and methods: SECS were synthesized by two reaction pathways, namely Michael addition and a nucleophilic substitution with sodium vinylsulfonate or sodium 2-bromoethanesulfonate (NaBES). Subsequently, these derivatives were used as reducing and capping agents for silver nanoparticles in a microwave-assisted reaction. The formed silver-chitosan core-shell particles were further surveyed in terms of their anticoagulant action by different coagulation assays focusing on the inhibition of either thrombin or cofactor Xa. Results: In-depth characterization revealed a sulfoalkylation of chitosan mainly on its sterically favored O6-position. Moreover, comparably high average degrees of substitution with sulfoethyl groups (DSSE) of up to 1.05 were realized in reactions with NaBES. The harsh reaction conditions led to significant chain degradation and consequently, SECS exhibits masses of <50 kDa. Throughout the following microwave reaction, stable nanoparticles were obtained only from highly substituted products because they provide a sufficient charge density that prevented particles from aggregation. High-resolution transmission electron microscopy images reveal that the silver core (diameter ~8 nm) is surrounded by a 1–2 nm thick SECS layer. These core-shell particles and the SECS itself exhibit an inhibiting activity, especially on cofactor Xa. Conclusion: This interesting model system enabled the investigation of structure–property correlations in the course of nanoparticle formation and anticoagulant activity of SECS and may lead to completely new anticoagulants on the basis of chitosan-capped nanoparticles. Keywords: chitosan ethylsulfonate, silver nanoparticles, antithrombotic activity, cofactor XaHeise KHobisch MSacarescu LMaver UHobisch JReichelt TSega MFischer SSpirk SDove Medical Pressarticlechitosan ethylsulfonatesilver nanoparticlesantithrombotic activitycofactor XaMedicine (General)R5-920ENInternational Journal of Nanomedicine, Vol Volume 13, Pp 4881-4894 (2018)
institution	DOAJ
collection	DOAJ
language	EN
topic	chitosan ethylsulfonate silver nanoparticles antithrombotic activity cofactor Xa Medicine (General) R5-920
spellingShingle	chitosan ethylsulfonate silver nanoparticles antithrombotic activity cofactor Xa Medicine (General) R5-920 Heise K Hobisch M Sacarescu L Maver U Hobisch J Reichelt T Sega M Fischer S Spirk S Low-molecular-weight sulfonated chitosan as template for anticoagulant nanoparticles
description	Katja Heise,1,2 Mathias Hobisch,3,4 Liviu Sacarescu,5 Uros Maver,6 Josefine Hobisch,3 Tobias Reichelt,7 Marija Sega,6 Steffen Fischer,1 Stefan Spirk3,4 Members of EPNOE and NAWI Graz 1Institute of Plant and Wood Chemistry, Technische Universität Dresden, Tharandt, Germany; 2Department of Bioproducts and Biosystems, Aalto University, Espoo, Finland; 3Institute for Chemistry and Technology of Materials, Graz University of Technology, Graz, Austria; 4Institute for Paper, Pulp and Fiber Technology, Graz University of Technology, Graz, Austria; 5“Petru Poni” Institute of Macromolecular Chemistry, Romanian Academy, Iasi, Romania; 6Faculty of Medicine, University of Maribor, Maribor, Slovenia; 7Zentrum für Bucherhaltung GmbH, Leipzig, Germany Purpose: In this work, low-molecular-weight sulfoethyl chitosan (SECS) was used as a model template for the generation of silver core-shell nanoparticles with high potential as anticoagulants for medical applications. Materials and methods: SECS were synthesized by two reaction pathways, namely Michael addition and a nucleophilic substitution with sodium vinylsulfonate or sodium 2-bromoethanesulfonate (NaBES). Subsequently, these derivatives were used as reducing and capping agents for silver nanoparticles in a microwave-assisted reaction. The formed silver-chitosan core-shell particles were further surveyed in terms of their anticoagulant action by different coagulation assays focusing on the inhibition of either thrombin or cofactor Xa. Results: In-depth characterization revealed a sulfoalkylation of chitosan mainly on its sterically favored O6-position. Moreover, comparably high average degrees of substitution with sulfoethyl groups (DSSE) of up to 1.05 were realized in reactions with NaBES. The harsh reaction conditions led to significant chain degradation and consequently, SECS exhibits masses of <50 kDa. Throughout the following microwave reaction, stable nanoparticles were obtained only from highly substituted products because they provide a sufficient charge density that prevented particles from aggregation. High-resolution transmission electron microscopy images reveal that the silver core (diameter ~8 nm) is surrounded by a 1–2 nm thick SECS layer. These core-shell particles and the SECS itself exhibit an inhibiting activity, especially on cofactor Xa. Conclusion: This interesting model system enabled the investigation of structure–property correlations in the course of nanoparticle formation and anticoagulant activity of SECS and may lead to completely new anticoagulants on the basis of chitosan-capped nanoparticles. Keywords: chitosan ethylsulfonate, silver nanoparticles, antithrombotic activity, cofactor Xa
format	article
author	Heise K Hobisch M Sacarescu L Maver U Hobisch J Reichelt T Sega M Fischer S Spirk S
author_facet	Heise K Hobisch M Sacarescu L Maver U Hobisch J Reichelt T Sega M Fischer S Spirk S
author_sort	Heise K
title	Low-molecular-weight sulfonated chitosan as template for anticoagulant nanoparticles
title_short	Low-molecular-weight sulfonated chitosan as template for anticoagulant nanoparticles
title_full	Low-molecular-weight sulfonated chitosan as template for anticoagulant nanoparticles
title_fullStr	Low-molecular-weight sulfonated chitosan as template for anticoagulant nanoparticles
title_full_unstemmed	Low-molecular-weight sulfonated chitosan as template for anticoagulant nanoparticles
title_sort	low-molecular-weight sulfonated chitosan as template for anticoagulant nanoparticles
publisher	Dove Medical Press
publishDate	2018
url	https://doaj.org/article/2315fc8251524d369b30ff280bdc9575
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Low-molecular-weight sulfonated chitosan as template for anticoagulant nanoparticles

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