Show simple item record

Tailoring Guanosine Hydrogels for Various Applications

dc.contributor.advisorDavis, Jeffery Ten_US
dc.contributor.authorPlank, Taylor Nicoleen_US
dc.date.accessioned2018-07-17T06:16:10Z
dc.date.available2018-07-17T06:16:10Z
dc.date.issued2018en_US
dc.identifierhttps://doi.org/10.13016/M2DJ58K8K
dc.identifier.urihttp://hdl.handle.net/1903/20986
dc.description.abstractSupramolecular hydrogels are of current interest for their ease of use, potential biocompatibility, and reactivity to stimuli. These gel materials have found use in a number of fields ranging from drug delivery and tissue engineering to sensing and environmental remediation. For over a century, guanosine (G 1) and its derivatives have been known to form hydrogels based on self-assembled G4-quartet structures. Recent research has focused on extending the lifetime stability of these hydrogels and modifying their properties to better suit the gels for applications in multiple fields. One such method involves the mixing of G 1 (or G-derivatives) with 0.5 eq of KB(OH)4, which results in the formation of guanosine-borate (GB) diesters. The GB-diesters self-assemble into G4-quartets stabilized by K+, the G4-quartets then stack to form wires that entangle to make a fibrous hydrogel network. This thesis details modifications of this GB-hydrogel system and explores applications of the resulting hydrogels. Modification of the 5ʹ-OH group of G 1 to form 5ʹ-deoxy-5ʹ-iodoguanosine (5ʹ-IG 2) results in a hydrogel that self-destructs via intramolecular cyclization to 5ʹ-deoxy-N3,5ʹ-cycloguanosine (5ʹ-cG 3). Guanine analog drugs can be incorporated into this hydrogel network and then released upon self-destruction of the gel. Substitution of boric acid with benzene-1,4-diboronic acid (BDBA 4) to form hydrogels with G 1 and K+ results in hydrogels that can be crosslinked with Mg2+. These G-BDBA-Mg hydrogels have a lower critical gelator concentration (cgc) than their non-crosslinked counterparts and can be used for cell growth applications. Utilizing binary mixtures of 8-aminoguanosine (8AmG 5) with G 1 allows for the formation of hydrogels with various salts. Hydrogels made of different salts preferentially absorb either cationic or anionic dyes from water, making them candidates for use in environmental remediation. Other 8-substituted G-analogs, including, 8-bromoguanosine (8BrG 6), 8-iodoguanosine (8IG 7), and 8-morpholinoguanosine (8morphG 8) can be used in binary mixtures with G 1 to form gels at room temperature upon mixing with KB(OH)4. Room temperature hydrogels have potential applications in enzyme immobilization, drug encapsulation, and environmental cleanup.en_US
dc.language.isoenen_US
dc.titleTailoring Guanosine Hydrogels for Various Applicationsen_US
dc.typeDissertationen_US
dc.contributor.publisherDigital Repository at the University of Marylanden_US
dc.contributor.publisherUniversity of Maryland (College Park, Md.)en_US
dc.contributor.departmentChemistryen_US
dc.subject.pqcontrolledChemistryen_US
dc.subject.pqcontrolledOrganic chemistryen_US
dc.subject.pquncontrolledG-quarteten_US
dc.subject.pquncontrolledguanosineen_US
dc.subject.pquncontrolledhydrogelen_US
dc.subject.pquncontrolledself-assemblyen_US
dc.subject.pquncontrolledsupramolecularen_US
dc.subject.pquncontrolledwateren_US


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record