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Electrospinning of pyrazole-isothiazole derivatives: nanofibers from small molecules

机译:吡唑 - 异噻唑衍生物的静电纺丝:来自小分子的纳米纤维

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摘要

We investigate the electrospinning of small molecules, specifically designed peptide derivatives of the pyrazole-isothiazole scaffold. Such non-natural peptides enhance the spectrum of fundamental materials used for electrospinning. Unlike standard electrospun materials, our peptides are not polymeric, but able to aggregate in solution and especially during processing. They contain donor/acceptor groups that can form hydrogen bonds, and groups that are able to generate pi-stacking interactions, which are known as important requirements for assembly processes. The pyrazole-isothiazole derivatives were synthesized by means of a 1,3-dipolar cycloaddition reaction, which is completely regioselective, affording only one isomer. We demonstrate that our compounds can be electrospun from fluoroalcohol solution into solid, quasi-endless micro- and nanofibers. The electrospinnability varies substantially, depending on the amino acids linked to the scaffold. Some compounds provide only short fibers, while Fmoc-glycyl-(N-benzyl)-pyrazole-isothiazole-tert-butyl carboxylate-1,1-dioxide forms continuous, homogenous, and bead-free fibers (droplet-like beads are a common problem in electrospinning). We analyzed the compounds and the fibers with various spectroscopic techniques (MS, IR and Raman). Electrospinning does not change chemical composition and configuration, suggesting the monomeric form of the compounds even in the fibers. Interestingly, we found that the stereochemistry of the scaffold can affect the ability of the peptide to be electrospun.
机译:我们研究了小分子的静电纺丝,专门设计了吡唑 - 异噻唑支架的肽衍生物。这种非天然肽增强了用于静电纺丝的基本材料的光谱。与标准的电纺材料不同,我们的肽不是聚合物,但能够在溶液中聚集,特别是在加工过程中。它们含有可以形成氢键的供体/受体基团,以及能够产生PI堆叠相互作用的组,其被称为组装过程的重要要求。通过1,3-偶极环加油反应合成吡唑 - 异噻唑衍生物,其是完全区域选择性的,只有一种异构体。我们证明我们的化合物可以从氟代醇溶液从氟代醇溶液静电,进入固体,准无环的微纤维和纳米纤维。电动术力基本上变化,取决于与支架连接的氨基酸。一些化合物仅提供短纤维,而FMOC-甘氨酸 - (N-苄基) - 吡唑 - 异噻唑 - 叔丁基羧酸盐-1,1-二氧化酯形成连续,均匀的和无胎珠纤维(液滴状珠子是常见的静电纺丝问题)。我们用各种光谱技术(MS,IR和拉曼)分析化合物和纤维)。静电纺丝不会改变化学成分和配置,表明甚至在纤维中的化合物的单体形式。有趣的是,我们发现支架的立体化学可以影响肽的能力是电纺器纺丝的能力。

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  • 来源
    《RSC Advances》 |2019年第36期|共8页
  • 作者单位

    Univ Milan Gen &

    Organ Chem Sect A Marchesini Dept Pharmaceut Sci Via Venezian 21 I-20133 Milan Italy;

    CIC nanoGUNE Tolosa Hiribidea 76 Donostia San Sebastian 20018 Spain;

    Dept Pharmaceut &

    Pharmacol Sci Via Marzolo 5 I-35131 Padua Italy;

    Univ Milan Gen &

    Organ Chem Sect A Marchesini Dept Pharmaceut Sci Via Venezian 21 I-20133 Milan Italy;

    Univ Milan Gen &

    Organ Chem Sect A Marchesini Dept Pharmaceut Sci Via Venezian 21 I-20133 Milan Italy;

    CIC nanoGUNE Tolosa Hiribidea 76 Donostia San Sebastian 20018 Spain;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
  • 关键词

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