Microwave-assisted synthesis of crosslinked ureido chitosan for hemostatic applications

Microwave-assisted synthesis of crosslinked ureido chitosan for hemostatic applications

In this study, we present a facile method for introducing hydrophilic ureido groups (NH2-CO-NH-) into chitosan using a microwave-assisted reaction with molten urea, with the aim of enhancing chitosan's interaction with blood components for improved hemostasis. The formation of the ureido groups...

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Bibliographic Details
Published in:International journal of biological macromolecules Vol. 260; no. Pt 2; p. 129648
Main Authors: Ravishankar, Kartik, Km, Shelly, Sreekumar, Sreelekshmi, Sivan, Sisira, Kiran, Manikantan Syamala, Lobo, Nitin Prakash, Jaisankar, Sellamuthu N., Raghavachari, Dhamodharan
Format: Journal Article
Language:English
Published: Netherlands Elsevier B.V 01-03-2024
Subjects:
Carbamate
Carbamates
Chitosan
Chitosan - chemistry
Hemostasis
Hemostatics
Microwaves
Ureido
Ureido
Carbamate
Chitosan
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Summary:In this study, we present a facile method for introducing hydrophilic ureido groups (NH2-CO-NH-) into chitosan using a microwave-assisted reaction with molten urea, with the aim of enhancing chitosan's interaction with blood components for improved hemostasis. The formation of the ureido groups through nucleophilic addition reaction between the amine groups in chitosan and in situ generated isocyanic acid was confirmed by FTIR, CP/TOSS 13C NMR, and CP/MAS 15N NMR spectroscopic techniques. However, in stark contrast to the glucans, the said modification introduced extensive crosslinking in chitosan. Spectroscopic studies identified these crosslinks as carbamate bridges (-NH-COO-), which were likely formed by the reaction between the ureido groups and hydroxyl groups of adjacent chains through an isocyanate intermediate. These carbamate bridges improved ureido chitosan's environmental stability, making it particularly resistant to changes in pH and temperature. In comparison to chitosan, the crosslinked ureido chitosan synthesized here exhibited good biocompatibility and cell adhesion, rapidly arrested the bleeding in a punctured artery with minimal hemolysis, and induced early activation and aggregation of platelets. These properties render it an invaluable material for applications in hemostasis, particularly in scenarios that necessitate stability against pH variations and degradation. [Display omitted] •Ureido chitosan was prepared by reacting chitosan with molten urea using microwaves.•Unlike glucans, chitosan underwent extensive crosslinking during the reaction.•Crosslinking was due to carbamate bridges formed through the ureido-hydroxyl reaction.•Crosslinked ureido chitosan was biocompatible, and rapidly arrested the bleeding.•Crosslinked ureido chitosan can act as pH/degradation-resistant haemostatic material.
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ISSN:0141-8130
1879-0003
DOI:10.1016/j.ijbiomac.2024.129648