Fluorescent Derivatives of Prostamides: Tools for Studying Anti-Cancer Activity

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dc.access.optionRestricted Campus Access Only
dc.contributor.advisorAllen, William E.
dc.contributor.authorStanley, Jordan Lynne
dc.contributor.departmentChemistry
dc.date.accessioned2018-08-14T15:04:33Z
dc.date.available2020-08-01T08:01:52Z
dc.date.created2018-08
dc.date.issued2018-07-23
dc.date.submittedAugust 2018
dc.date.updated2018-08-09T20:03:27Z
dc.degree.departmentChemistry
dc.degree.disciplineMS-Chemistry
dc.degree.grantorEast Carolina University
dc.degree.levelMasters
dc.degree.nameM.S.
dc.description.abstractThe endocannabinoid arachidonoyl ethanolamide (AEA) and prostaglandins derived from it selectively induce apoptosis in tumorigenic cell lines due to overexpression of COX-2. It is likely that a novel J-series prostamide, 15-deoxy-[delta]12,14-prostaglandin J2-ethanolamide (15d-PMJ2), is the cytotoxic mediator of AEA-induced apoptosis. Conjugation of a fluorescent group to prostamides of interest may be helpful in determining localization and pharmacokinetic properties needed for clinical development. The synthetic flexibility and bright luminescence of naphthalimides make them attractive probes for this purpose. Previous studies in our labs focused on identifying substituents on naphthalimide that cause minimal interference with intracellular drug localization and metabolism. Those studies indicated that a 4-morpholino naphthalimide would be a suitable probe for conjugation based on its lack of cytotoxicity. Unfortunately, we found that this probe renders AEA inactive, presumably by preventing its cyclization into prostamides. We hypothesize that conjugation of the 4-morpholino naphthalimide to an already-cyclized metabolite, such as 15d-PMJ2, will allow the drug to retain its activity.
dc.embargo.lift2020-08-01
dc.format.mimetypeapplication/pdf
dc.identifier.urihttp://hdl.handle.net/10342/6956
dc.language.isoen
dc.publisherEast Carolina University
dc.subjectNaphthalimides
dc.subjectProstamides
dc.subjectFluorescence
dc.subject.lcshCancer--Genetic aspects
dc.subject.lcshCancer--Prevention
dc.titleFluorescent Derivatives of Prostamides: Tools for Studying Anti-Cancer Activity
dc.typeMaster's Thesis
dc.type.materialtext

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