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Synthesis of polysaccharide mimetics for bioactive surface coatings and artificial glycosylation of proteins.

机译：用于生物活性表面涂层的多糖模拟物的合成和蛋白质的人工糖基化。

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摘要

Natural saccharides are involved in numerous biological and although the full spectrum of their functions and mechanism has not been revealed yet, saccharides have drawn increasing interest in the biomedical field. However, the application of natural saccharides has been limited due to difficulties in their synthesis and modification.;Glycopolymers have been sought as surrogates. In this thesis, new polymerization techniques for the synthesis of saccharide mimics are discussed. Recent advancement in the synthesis of glycopolymers by controlled radical polymerization (CRP) techniques is discussed in Chapter 1.;Chapter 2 describes the synthesis of aminooxy end-functionalized poly( N-isopropylacrylamide) (pNIPAAm) by reversible addition-fragmentation chain transfer (RAFT) polymerization. pNIPAAm was conjugated to bovine serum albumin (BSA) modified with ketone groups. pNIPAAm was also immobilized on a gold surface and an aldehyde-modified heparin (a sulfated polysaccharide) was then conjugated to the pNIPAAm surface via oxime chemistry. This technique could be used for the stabilization and storage of growth factors on surfaces.;In Chapter 3, synthesis of a pyridyl-disulfide glycopolymers with N-acetyl-D-glucosamine pendant groups by atom transfer radical polymerization (ATRP) is discussed. The polymer was patterned on a surface by microcontact printing and was visualized by fluorescence microscopy. The glycopolymers was also conjugated to double-stranded short interfering RNA (siRNA). This highly efficient synthesis and one-step conjugation system offers great potential for the study of sugar-targeted siRNA gene therapy.;Chapter 4 and 5 describes the uses of sulfonated polymers as heparin mimics. In Chapter 4, poly(sodium 4-styrene sulfonate-co-poly(ethylene glycol) methacrylate) (pSS-co-pPEGMA) was synthesized via RAFT polymerization and immobilized on a gold surface. The surface was employed to study the binding of pSS-co-pPEGMA towards vascular endothelial growth factor (VEGF) and basic fibroblast growth factor (bFGF) by surface plasmon resonance (SPR). In Chapter 5, a series of sulfonated polymers were investigated as potential heparin mimics. The polymers utilized in the study were poly(sodium 4-styrene sulfonate- co-2-hydroxyethyl methacrylate) (pSS-co-pHEMA), poly(sodium poly(sodium 2-acrylamido-2-methyl propane sulfonate-co-2-hydroxyethyl methacrylate) (pAMPS-co-pHEMA), and poly(potassium 3-(methacryloyloxy)-1-propane sulfonate-co-2-hydroxyethyl methacrylate) (pSPMA-co-pHEMA). SPR studies were performed in order to screen their binding affinities to VEGF. These results suggest that these sulfonated copolymers could serve as heparin mimics.
机译：天然糖与许多生物学有关，尽管尚未揭示其功能和机理的全谱，但糖已在生物医学领域引起了越来越多的兴趣。然而，由于天然糖的合成和修饰困难，其应用受到了限制。本文探讨了合成糖模拟物的新聚合技术。第1章讨论了通过可控自由基聚合（CRP）技术合成糖聚合物的最新进展；第2章介绍了可逆加成-断裂链转移（RAFT）合成氨基氧基末端官能化聚N-异丙基丙烯酰胺（pNIPAAm）的方法。 ）聚合。将pNIPAAm与经酮基修饰的牛血清白蛋白（BSA）偶联。 pNIPAAm也固定在金表面，然后通过肟化学将醛改性的肝素（硫酸化多糖）偶联到pNIPAAm表面。该技术可用于表面生长因子的稳定和存储。第三章讨论了通过原子转移自由基聚合（ATRP）合成具有N-乙酰基-D-葡糖胺侧基的吡啶基-二硫化糖聚合物。通过微接触印刷将聚合物图案化在表面上，并通过荧光显微镜观察。糖聚合物也缀合至双链短干扰RNA（siRNA）。这种高效的合成和一步结合系统为糖靶向siRNA基因疗法的研究提供了巨大的潜力。第四章和第五章介绍了磺化聚合物作为肝素模拟物的用途。在第4章中，通过RAFT聚合反应合成了聚（4-苯乙烯磺酸钠-共-聚（甲基丙烯酸乙二醇酯）（pSS-co-pPEGMA）），并将其固定在金表面。该表面用于通过表面等离振子共振（SPR）研究pSS-co-pPEGMA与血管内皮生长因子（VEGF）和碱性成纤维细胞生长因子（bFGF）的结合。在第5章中，研究了一系列磺化聚合物作为潜在的肝素模拟物。在研究中使用的聚合物是聚（4-苯乙烯磺酸钠-甲基丙烯酸2-羟乙基酯）（pSS-co-pHEMA），聚（2-丙烯酰胺基-2-甲基丙烷磺酸钠-甲基-2-磺酸钠）。进行了SPR研究，以筛选它们的聚苯乙烯3-甲基丙烯酸羟乙酯（pAMPS-co-pHEMA）和聚3-甲基丙烯酸（甲基丙烯酰氧基）-1-丙烷磺酸盐-甲基丙烯酸-2-羟乙酯（pSPMA-co-pHEMA）。这些结果表明这些磺化共聚物可以用作肝素的模拟物。

著录项

  • 作者

    Vazquez Dorbatt, Vimary.;

  • 作者单位

    University of California, Los Angeles.;

  • 授予单位 University of California, Los Angeles.;
  • 学科 Chemistry Organic.;Chemistry Polymer.
  • 学位 Ph.D.
  • 年度 2009
  • 页码 150 p.
  • 总页数 150
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

  • 入库时间 2022-08-17 11:38:30

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