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Thiazolidine chemistry revisited: a fast, efficient and stable click-type reaction at physiological pH
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Polymer Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Polymer Chemistry.ORCID iD: 0000-0002-7256-0758
Bioengineering and Nanomedicine Lab, Faculty of Biomedical Sciences and Engineering, Tampere University of Technology, and BioMediTech Institute, 33720, Tampere, Finland.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Polymer Chemistry.ORCID iD: 0000-0001-6947-9601
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2018 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 54, no 88, p. 12507-12510Article in journal (Refereed) Published
Abstract [en]

We describe the fast reaction kinetics between 1,2-aminothiols and aldehydes. Under physiological conditions such a click-type reaction afforded a thiazolidine product that remains stable and did not require any catalyst. This type of bioorthogonal reaction offers enormous potential for the coupling of biomolecules in an efficient and biocompatible manner.

Place, publisher, year, edition, pages
2018. Vol. 54, no 88, p. 12507-12510
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-364896DOI: 10.1039/c8cc05405cISI: 000448947000019PubMedID: 30345438OAI: oai:DiVA.org:uu-364896DiVA, id: diva2:1261170
Available from: 2018-11-06 Created: 2018-11-06 Last updated: 2019-06-26Bibliographically approved
In thesis
1. Insights into Covalent Chemistry for the Developmen­t of Biomaterials
Open this publication in new window or tab >>Insights into Covalent Chemistry for the Developmen­t of Biomaterials
2019 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Covalent cross-linking chemistry is currently exploited in the preparation of biomaterial for biomedical applications. Choice of these chemistries for the preparation of biomaterials and bioconjugates strongly influences the biological output of these materials. Therefore, this thesis aims to develop novel bioconjugation strategies understanding their advantages and drawbacks. Our results provide new insight to adapt these chemical transformations for a specific application.

The first part of this thesis points out the relevance of tuning different properties of biomaterials with specific emphasis on the development of hyaluronic acid (HA) hydrogels. The second part of the thesis describes how different chemical transformations including hydrazone formation (Paper I), thiazolidine formation (Paper II), cross-aldol addition reaction (Paper III) and disulfide formation (Paper IV) dictate material properties.

This thesis explores both basic organic reaction mechanism and application of these reactions to influence material characteristics. The detailed study of the reaction conditions, kinetics, and stability of the products will help to understand the mechanical properties, hydrolytic stability, and degradability of the materials described here.

Additionally, we performed degradation studies of gadolinium labeled HA hydrogels using magnetic resonance imaging. Furthermore, we also explored post-synthetic modification of hydrogels to link model fluorescent moieties as well as explored the tissue adhesive properties using Schiff-base formation.

In summary, this thesis presents a selection of different covalent chemistries for the design of advanced biomaterials. The advantages and disadvantages of these chemistries are rigorously investigated. We believe, such an investigation provides a better understanding of the bioconjugation strategies for the preparation of biomaterials with potential clinical translation.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2019. p. 64
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1768
Keywords
hyaluronic acid, hydrogel, biomaterials, covalent chemistry, biomedical applications, MRI
National Category
Materials Chemistry Polymer Chemistry Organic Chemistry
Research subject
Chemistry with specialization in Materials Chemistry; Chemistry with specialization in Polymer Chemistry
Identifiers
urn:nbn:se:uu:diva-375002 (URN)978-91-513-0564-6 (ISBN)
Public defence
2019-03-14, Häggsalen, 10132, Ångströmlaboratoriet, Lägerhyddsvägen 1, Uppsala, 13:15 (English)
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Supervisors
Available from: 2019-02-21 Created: 2019-01-24 Last updated: 2019-02-21

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Bermejo-Velasco, DanielNawale, Ganesh N.Hilborn, JönsVarghese, Oommen P.

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