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Interfacial Bioorthogonal Chemistry for Biomaterials Synthesis and Patterning and Development of Catalytic Method for "Turning-On" the Tetrazine Ligation.

Record Type:	Language materials, manuscript : Monograph/item
Title/Author:	Interfacial Bioorthogonal Chemistry for Biomaterials Synthesis and Patterning and Development of Catalytic Method for "Turning-On" the Tetrazine Ligation./
Author:	Zhang, Han.
Description:	1 online resource (281 pages)
Notes:	Source: Dissertation Abstracts International, Volume: 79-02(E), Section: B.
Subject:	Organic chemistry. -
Online resource:	click for full text (PQDT)
ISBN:	9780355251357

Interfacial Bioorthogonal Chemistry for Biomaterials Synthesis and Patterning and Development of Catalytic Method for "Turning-On" the Tetrazine Ligation.
Zhang, Han.

Interfacial Bioorthogonal Chemistry for Biomaterials Synthesis and Patterning and Development of Catalytic Method for "Turning-On" the Tetrazine Ligation. - 1 online resource (281 pages)

Source: Dissertation Abstracts International, Volume: 79-02(E), Section: B.

Thesis (Ph.D.)--University of Delaware, 2017.

Includes bibliographical references

The bioorthogonal trans-cyclooctene-tetrazine ligation has emerged into a powerful tool in the field of biomedical research. The development and the versatile applications of tetrazine ligation was made possible by the advancement of trans-cyclooctene synthesis. Based on the previous art of photoisomerization methods in Fox group, I carried out the first practical photosynthesis of trans-cycloheptene derivatives that were stabilized as silver(I) complexes form, as well as the photoisomerization of silicon-containing hetero- trans-cycloheptene derivatives. The reactivity of both the trans-cycloheptene silver(I) complexes and the hetero-trans-cycloheptene derivatives were investigated.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2018

Mode of access: World Wide Web

ISBN: 9780355251357Subjects--Topical Terms:

1148722
Organic chemistry.
Index Terms--Genre/Form:

554714
Electronic books.

Interfacial Bioorthogonal Chemistry for Biomaterials Synthesis and Patterning and Development of Catalytic Method for "Turning-On" the Tetrazine Ligation.
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245 1 0 $a Interfacial Bioorthogonal Chemistry for Biomaterials Synthesis and Patterning and Development of Catalytic Method for "Turning-On" the Tetrazine Ligation.
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300 $a 1 online resource (281 pages)
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500 $a Source: Dissertation Abstracts International, Volume: 79-02(E), Section: B.
500 $a Adviser: Joseph M. Fox.
502 $a Thesis (Ph.D.)--University of Delaware, 2017.
504 $a Includes bibliographical references
520 $a The bioorthogonal trans-cyclooctene-tetrazine ligation has emerged into a powerful tool in the field of biomedical research. The development and the versatile applications of tetrazine ligation was made possible by the advancement of trans-cyclooctene synthesis. Based on the previous art of photoisomerization methods in Fox group, I carried out the first practical photosynthesis of trans-cycloheptene derivatives that were stabilized as silver(I) complexes form, as well as the photoisomerization of silicon-containing hetero- trans-cycloheptene derivatives. The reactivity of both the trans-cycloheptene silver(I) complexes and the hetero-trans-cycloheptene derivatives were investigated.
520 $a Based on the rapid trans-cyclooctene-tetrazine ligation, first example of interfacial crosslinking will be described in Chapter 2. Bioocompatible hyaluronic acid-based hydrogel microspheres and channels were generated in a diffusion controlled fashion. These hydrogels can be covalently tagged with 3D resolution without the help of any external stimulus or triggers. An in vitro tumor model was achieved by 3D encapsulation and culture of LNCaP prostate cancer cells.
520 $a Also included in Chapter 2 will be a novel interfacial polymerization strategy developed for the synthesis of hybrid multiblock copolymer. Meter-long copolymer fibers were pulled out of interface of two immiscible solutions. The unique modular approach enables the facile incorporation of functional peptides into the copolymer to fine-tune its biological properties. A fibronectin-derived peptide was successfully introduced onto the fibers during the polymerization and dramatically promoted the attachment and alignment of fibroblasts and myoepithelial-like cells.
520 $a In Chapter 3, a novel method to activate rapid bioorthogonal reactivity catalytically will be described. This was achieved by catalytic conversion of an unreactive, latent dihydrotetrazine to reaction-ready tetrazine functionality. Series of long wavelength photosensitizers were found to catalyze the oxidation of DHTz to Tz effieciently in the presence of light and air. Horseradish peroxidase (HRP) was found to catalyze the oxidation at nanomolar concentrations in absence of peroxide. These methods can provide a milder and more physiology-friendly way to "turn-on" rapid tetrazine ligation reactivity with great promise in extending to a wide range of applications in materials, cellular, and in vivo systems.
520 $a Moreover, based on the previous bioorthogonal interfacial polymerization developed from our group, DHTz functionality can be successfully incorporated onto the copolymer fibers, which can be activated postsynthetically by either light or an HRP enzyme. Conjugations with small molecule fluorophores, cell-instructive peptide sequences and fluorescent proteins were accomplished, providing a new tool for modulating the cell adhesive properties of a biomaterial.
520 $a TCO-tetrazine ligation has emerged as a multifaceted strategy in polymer and biomaterials discovery, bringing promising results and exhilarating progress. The versatile materials we developed here will prove useful and become indispensable elements in the tissue engineering toolbox.
533 $a Electronic reproduction. $b Ann Arbor, Mich. : $c ProQuest, $d 2018
538 $a Mode of access: World Wide Web
650 4 $a Organic chemistry. $3 1148722
650 4 $a Materials science. $3 557839
650 4 $a Biomedical engineering. $3 588770
655 7 $a Electronic books. $2 local $3 554714
690 $a 0490
690 $a 0794
690 $a 0541
710 2 $a ProQuest Information and Learning Co. $3 1178819
710 2 $a University of Delaware. $b Chemistry and Biochemistry. $3 1187217
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10263951 $z click for full text (PQDT)