Syntheses and self-assembly of novel asparagine-derived amphiphiles: Applications in the encapsulation of proteins, hydrophobic, and hydrophilic drug models

dc.contributor.advisorNegrete, George R.
dc.contributor.authorMfuh, Adelphe Mbufung
dc.contributor.committeeMemberJarrett, Harry W.
dc.contributor.committeeMemberZhao, John Cong-Gui
dc.contributor.committeeMemberRenthal, Robert D.
dc.contributor.committeeMemberGoins, Beth A. Goins A.
dc.date.accessioned2024-02-12T15:39:56Z
dc.date.available2024-02-12T15:39:56Z
dc.date.issued2012
dc.descriptionThis item is available only to currently enrolled UTSA students, faculty or staff. To download, navigate to Log In in the top right-hand corner of this screen, then select Log in with my UTSA ID.
dc.description.abstractThis thesis focuses mainly on the synthesis, characterization, and self-assembly of a novel series of asparagine-derived amphiphiles and their use in the preparation and stabilization of nano and microcapsules for the encapsulation of proteins, and hydrophilic and hydrophobic drug models. Chapter 1 gives a brief literature overview of lipid molecular assembly, which covers some aspects of morphological analyses, encapsulation of chemical entity and some reported characterization techniques of supramolecular assemblies. It introduces the scope of this dissertation and contains some information on stimulus responsive liposomal systems for controlled release of drug models. Chapter 2 introduces a novel asparagine-derived lipid bearing two fatty chains (C11 and C17) and a tetrahydropyrimidinone head group. It presents information on the synthesis and characterization of this lipid and describes the self-assembly and effects of this lipid in distearoyl phosphatidyl choline bilayer. Chapter 3 presents the synthesis and characterization of a series of ALAn,m (where n and m represent the length of the hydrocarbon chains on the asparagine-derived, heterocyclic head group). It contains data on the effect of chain length, solvent media and head group ionization on the conformational equilibrium about a tertiary amide bond in ALAn,m. The chapter also examines the influence of chain length on ALAn,m on the colloidal stability of DSPC liposomes. Chapter 4 presents the first example of an N,N-acetal linkage in a novel pH responsive nanocarrier system obtained from the cyclocondensation of dodecanal with sodium asparaginate. Data is presented on the spontaneous self-assembly, encapsulation studies and morphological characterization of the nano-systems with the inclusion of cholesterol as additive. Chapter 5 presents the development of a photoresponsive nanocarrier via the self- assembly of an asparagine-derived lipid containing a coumarin unit in the hydrophobic domain. The supramolecular assemblies of this lipid were examined for the ability to encapsulate and release chemical entity in response to UV-assisted [2+2]-photodimerization. Chapter 6 presents the fabrication of an organic core/inorganic shell microcapsules from the catanionic self-assemblies of a series of symmetrical asparagine-derived bolaamphiphiles and polyallyl amine, followed by surfacing coating with silica nanoparticles. Unlike layer-by-layer or polymer salt aggregates (PSA) capsules reported in the chemical literature, these particles show encapsulation for wider range of chemical entities with different solubility properties. Studies suggest that these particles efficiently encapsulated protoporphyrin IX. dimethylester, doxorubicin and a fluorescently labeled bovine serum albumin (FITC-BSA).
dc.description.departmentChemistry
dc.format.extent211 pages
dc.format.mimetypeapplication/pdf
dc.identifier.isbn9781267843203
dc.identifier.urihttps://hdl.handle.net/20.500.12588/4504
dc.languageen
dc.subjectAsparagine-derived lipid
dc.subjectBolaamphiphiles
dc.subjectCatanionic
dc.subjectcoumarin dimerization
dc.subjectEncapsulation
dc.subjectSelf-assembly
dc.subject.classificationOrganic chemistry
dc.subject.classificationChemistry
dc.subject.classificationNanotechnology
dc.subject.classificationNanoscience
dc.titleSyntheses and self-assembly of novel asparagine-derived amphiphiles: Applications in the encapsulation of proteins, hydrophobic, and hydrophilic drug models
dc.typeThesis
dc.type.dcmiText
dcterms.accessRightspq_closed
thesis.degree.departmentChemistry
thesis.degree.grantorUniversity of Texas at San Antonio
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy

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