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Towards Bioactive Rosette Nanotubes for Biomedical Applications Open Access


Other title
Bone Tissue Engineering
Type of item
Degree grantor
University of Alberta
Author or creator
Alsbaiee, Alaaeddin
Supervisor and department
Supervisor: Fenniri, Hicham (Department of Chemistry)
Co-supervisor: West, Frederick G (Department of Chemistry)
Examining committee member and department
Lowary, Todd (Department of Chemistry)
Campbell, Robert E (Department of Chemistry)
Petersen, Nils (Department of Chemistry)
MacLachlan, Mark (Department of Chemistry, University of British Columbia)
Department of Chemistry

Date accepted
Graduation date
Doctor of Philosophy
Degree level
Rosette nanotubes (RNTs) are bio-inspired nanomaterials generated from the self-assembly of a guanine-cytosine motif called the “G∧C” base. These nanotubular architectures are promising 2-D coating materials for bone tissue engineering applications, and delivery scaffolds for hydrophobic drug molecules in physiological media. For successful biomedical applications of RNTs however, it is necessary to: 1) explore the extent to which peptides on their outer surface can be tolerated, 2) develop radiolabeling methods to facilitate in vivo studies, and 3) extend the RNT inner diameter for enhanced drug encapsulation capability. This thesis aims to provide physical and synthetic tools in which to expand the scope of the RNTs for biomedical applications, particularly within the areas of bone tissue engineering and drug delivery. Chapter 1 provides a literature review of self-assembled nanomaterials that are based on bio-inspired building blocks including peptides and nucleic acids and are currently being investigated for biomedical applications. Given the importance of functionalizing such nanomaterials with peptides, Chapter 2 aims to demonstrate that RNTs can act as a scaffold to express three bioactive 11-amino acid-long peptides named A, B and C. Specifically, the synthesis and self-assembly of peptides (A-C)-functionalized twin G∧C motifs, (pA-TB, pB-TB and pC-TB) and a lysine-functionalized motif K1-TB, are presented. Next, three co-assembled RNT-constructs consisting of 90% of K1-TB and 10% of each of the peptide-TB conjugates are prepared. Circular dichroism in combination with microscopy techniques, provide evidence for the first time of the formation of bi-functionalized RNTs having a random mixed configuration. Chapter 3 introduces two radiolabeling strategies of RNTs for single photon emission computed tomography (SPECT) and positron emission tomography (PET) imaging techniques. In these strategies, the synthesis and self-assembly of RNTs, which are functionalized with an oxo-rhenium complex (for SPECT) and p-fluorobenzoate (for PET) are presented. Next, Chapter 4 describes a 13-step synthetic strategy to obtain an organic-soluble tetracyclic yG∧C motif for self-assembly into RNTs with a ca. 1.7 nm inner diameter for drug delivery applications. The self-assembly of this motif is then investigated using microscopy techniques. Finally, Chapter 5 highlights the significance and future directions of this work
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
Citation for previous publication
Alsbaiee, A.; Beingessner, R. L.; and Fenniri, H.; ‘Self-Assembled Nanomaterials for Tissue Engineering’; in ‘Nanomedicine: Technologies and Applications’; Webster, T. J. (ed); Woodhead Publishing Ltd, Cambridge, UK, 2012, Ch. 17, pp. 490-533Alsbaiee, A.; El Bakkari, M.; Fenniri, H. Mater. Res. Soc. Proc. 2011, 1316, mrsf10-1316-qq12-18, USAAlsbaiee, A.; St. Jules, M.; Beingessner, R. L.; Fenniri, H. Tet. Lett. 2012, 53, 1645-1651Alsbaiee, A.; St. Jules, M.; Beingessner, R. L.; Fenniri, H. Mater. Res. Soc. Proc. 2011, 1316, mrsf10-1316-qq03-12, USABorzsonyi, G.; Alsbaiee, A.; Beingessner, R. L.; Fenniri, H. J. Org. Chem. 2010, 75, 7233-7239

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