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dc.contributor.authorHardrict, Shauntrece Nicoleen
dc.date.accessioned2014-03-14T20:19:42Zen
dc.date.available2014-03-14T20:19:42Zen
dc.date.issued2009-11-05en
dc.identifier.otheretd-12032009-232246en
dc.identifier.urihttp://hdl.handle.net/10919/29903en
dc.description.abstractThe need for a preventative agent to curtail the rampant spread of HIV, other STDs and mucosal pathogens is urgent. Topical microbicides based on amphiphilic compounds have been identified as an attractive means toward this goal. Novel dendritic methacrylate macromonomers––di-tert-butyl 4-(2-tert-butoxycarbonyl-ethyl)-4-[3-(2-methacryoloxyethyl)ureido]heptandioate (MI) and di-tert-butyl 4-(2-tert-butoxycarbonylethyl)-4-[3-methyl-3-(2-methacryoloxyethyl)ureido]heptanedioate (MIII)––were synthesized, characterized, and subsequently polymerized via conventional free radical polymerization in acetonitrile employing AIBN as an initiator. Methyl 3-mercaptopropionate (MMP), a chain transfer agent, was employed to target low molecular weight (<10,000 g/mol) polymers. Dendronized homopolymers were prepared from MIII with varying MMP concentrations (0–10 mol%). MALDI-TOF MS characterized the homopolymer prepared with 10 mol% MMP (Mn = 2,481 g/mol). In the presence of MMP, MIII (5 to 25 mol%) was copolymerized with alkyl (methyl, ethyl, and n-butyl) methacrylates. Copolymer composition correlated well with monomer feed; Mns of 3–10K g/mol were observed. Ionizable polymers were achieved via acidolysis with trifluoroacetic acid; significant increases in Tg were observed. For the copolymers, the Tgs of the acids increased as the copolymer composition increased in MIII. For the homopolymers, Tgs decreased with increasing MMP concentration. The solubilities of carboxylic acid functional polymers were studied in 5 w/v % aqueous triethanolamine (aq TEA) at a concentration of 12.5 mg/mL. Clear, homogeneous solutions of the deprotected macromonomer, MIII(OH), homopolymer, PMIII(OH), and MIII(OH)/MMA copolymer series were observed; copolymer solubility decreased as the aliphatic chain length of the alkyl methacrylate increased. The amphiphilic dendronized polymer series incorporates many features shown beneficial in the pursuit of effective antimicrobial agents: amphiphilicity, multiple anionic functional groups, a polymer backbone, and aqueous solubility. Additionally, biological selectivity (e.g. cytotoxicity) is expected to be tunable through the control of molecular weight, alkyl chain length (n*), copolymer composition, and molecular architecture.en
dc.publisherVirginia Techen
dc.relation.haspartHardrict_SN_D_2009.pdfen
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subjecttopical microbicideen
dc.subjectionomeren
dc.subjectdendronized polymeren
dc.subjectamphiphileen
dc.titleDendronized Amphiphilic Copolymers Synthesized from Methacrylate Derivatives as Potential Topical Microbicidesen
dc.typeDissertationen
dc.contributor.departmentChemistryen
dc.description.degreePh. D.en
thesis.degree.namePh. D.en
thesis.degree.leveldoctoralen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.disciplineChemistryen
dc.contributor.committeememberRiffle, Judy S.en
dc.contributor.committeememberDavis, Richey M.en
dc.contributor.committeememberMcGrath, James E.en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-12032009-232246/en
dc.contributor.committeecochairGandour, Richard D.en
dc.contributor.committeecochairRichard, Turner S.en
dc.date.sdate2009-12-03en
dc.date.rdate2013-05-20en
dc.date.adate2010-01-10en


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