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The synthesis and study of bioerodible and biostable poly(organophosphazenes) for medical applications

Posted on:1994-09-30Degree:Ph.DType:Thesis
University:The Pennsylvania State UniversityCandidate:Pucher, Shawn RichardFull Text:PDF
GTID:2471390014492232Subject:Chemistry
Abstract/Summary:
This thesis is concerned with the synthesis of a relatively new class of inorganic polymers. Specifically, it involves the synthesis of poly(organophosphazenes), (NPR{dollar}sb2rbrack sb{lcub}rm n{rcub},{dollar} where R is an alkoxy, aryloxy, or an amino residue.; Four new types of polymers have been synthesized that bear {dollar}alpha{dollar}-D-glucosyl side groups and methylamino, trifluoroethoxy, phenoxy, or (methoxyethoxy)ethoxy cosubstituent groups. The syntheses were accomplished by the following sequence of reactions. First, the sodium salt of diacetone-D-glucose or the cosubstituent nucleophile was allowed to react with poly(dichlorophosphazene) to generate an intermediate formula, (NP(di-A-Gl){dollar}rm sb{lcub}x{rcub}(Cl)sb{lcub}y{rcub}rbrack sb{lcub}n{rcub}{dollar} or ({dollar}rm NP(Cl)sb{lcub}x{rcub}(OR)sb{lcub}y{rcub}rbrack sb{lcub}n{rcub},{dollar} with the ratio of x to y being determined by the ratio of reactants. Second, the cosubstituent (NHMe, OR, or di-A-Gl) was introduced to replace the remaining chlorines by methylamine or by the appropriate alkoxide or aryl oxide. Finally, the protecting groups on the glucosyl residues were removed by treatment with acid.; Eight water-soluble polyphosphazenes were examined for antibacterial activity. The antibacterial activity of cross-linked poly (di(methyoxyethoxyethoxy)phosphazene) hydrogels was investigated. A number of the high polymers, as well as the MEEP hydrogels, impeded bacterial growth.; Poly ((imidazolyl) (methylphenoxy)phosphazene) and poly ((ethyl glycinato)(methylphenoxy)phosphazene) were studied as potential polymeric supports for cells in tissue regeneration. Both imidazolyl and ethyl glycinato substituted polyphosphazenes supported the growth of MC3T3-E1 cells. These polyphosphazenes represent two systems whereby cell growth can be modulated by varying the nature of the hydrolytically sensitive side group.; Fifteen different poly ((amino acid ester)phosphazenes) were synthesized in order to study their crystalline character and hydrolysis behavior in the solution and solid states. The polymers were synthesized by treatment of poly(dichlorophosphazene) with a large excess of the appropriate amino acid ester. Several of these polymers were crystalline as measured by differential scanning calorimetry and by polarized optical microscopy. Hydrolysis studies were performed to estimate the rates of decomposition of these polymers. The potential applications of these polymers as biomedical materials is discussed.; Three different poly ((amino acid ester)phosphazenes) have been examined as potential drug delivery vehicles. (Abstract shortened by UMI.)...
Keywords/Search Tags:Poly, Amino acid ester, Synthesis, Phosphazene
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