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Selective Michael-type addition of a D-glucuronic acid derivative in the synthesis of model substances for uronic acid containing polysaccharides
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för materialkemi, Polymerkemi.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för materialkemi, Polymerkemi.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för materialkemi, Polymerkemi.
2008 (engelsk)Inngår i: Express Polymer Letters, ISSN 1788-618X, Vol. 2, nr 8, s. 553-559Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

A flexible protocol for the preparation of model substances for uronic acid containing polysaccharides is presented.We have synthesized a D-glucuronic acid derivative which is designed so that it easily can be conjugated with differentstructures and architectures by selective Michael-type addition. By successful coupling of the glucuronic acidderivative to polyethylene glycol with high degree of conversion, products were obtained that were easily characterized andwhich resembled polysaccharides in terms of solubility and purification methods that could be employed. The model substancecan potentially be used to facilitate optimization of low-degree modification reactions of high molecular weightD-glucuronic acid containing polysaccharides.

sted, utgiver, år, opplag, sider
2008. Vol. 2, nr 8, s. 553-559
Emneord [en]
polymer gels, polysaccharides, Michael-type addition, model substance, NMR
HSV kategori
Identifikatorer
URN: urn:nbn:se:uu:diva-97728DOI: 10.3144/expresspolymlett.2008.67ISI: 000263687000004OAI: oai:DiVA.org:uu-97728DiVA, id: diva2:172778
Tilgjengelig fra: 2008-11-14 Laget: 2008-11-14 Sist oppdatert: 2010-08-25bibliografisk kontrollert
Inngår i avhandling
1. Hyaluronan Derivatives and Injectable Gels for Tissue Engineering
Åpne denne publikasjonen i ny fane eller vindu >>Hyaluronan Derivatives and Injectable Gels for Tissue Engineering
2008 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The present work describes the preparation of hyaluronan derivatives and hydrogels with potential use in tissue engineering applications. A potentially injectable hydrogel consisting of hyaluronan and collagen was successfully used to grow neurons in vitro by encapsulation of neural stem and progenitor cells. Attempts were further made to establish a suitable modification strategy which could be used for the preparation of in vivo cross-linkable hyaluronan derivatives. The synthesis of a model substance consisting of a D-glucuronate derivative which could simplify the development of such a modification technique is described, although a new method to prepare hyaluronan derivatives was found without its use. The modification strategy involves the use of a triazine-reagent which enables the covalent attachment of hydrophilic and hydrophobic amines to hyaluronan carboxyl groups in a controlled fashion under mild conditions. Using triazine-activated amidation we synthesized an aldehyde-derivative of hyaluronan which was used to prepare gels by cross-linking with hydrazide-modified polyvinyl-alcohol. Gels were formed in less than 1 minute by mixing equal volumes of the polymer derivatives and they were subsequently used as a carrier for bone morphogenetic protein-2. An in vitro release study showed that approximately 88% of the growth factor is retained in the gel over a 4 week period. The ability to form new bone in vivo was further evaluated in an ectopic rat model by the injection of gels containing 30 µg BMP-2. Radiographic and histological examination 4 and 10 weeks after injection showed the formation of new bone without any signs of inflammation or foreign body response. Hydroxyapatite particles were further added to improve the mechanical properties of the gel, and a comparative study was conducted. This time the induced tissue consisted not only of bone, but also of interconnected cartilage and tendon, as confirmed by histology and immunohistochemistry.

sted, utgiver, år, opplag, sider
Uppsala: Universitetsbiblioteket, 2008. s. 51
Serie
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 573
Emneord
Hyaluronan, Hydrogel, Tissue Engineering, Scaffold, Minimally invasive strategy, Bone morphogenetic protein, Hydroxyapatite, Bone, Cartilage, Tendon
HSV kategori
Identifikatorer
urn:nbn:se:uu:diva-9357 (URN)978-91-554-7335-8 (ISBN)
Disputas
2008-12-05, Polhemsalen, Ångströmlaboratoriet, Lägerhyddsvägen 1, Uppsala, 09:00 (engelsk)
Opponent
Veileder
Tilgjengelig fra: 2008-11-14 Laget: 2008-11-14 Sist oppdatert: 2010-03-04bibliografisk kontrollert

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