Boc-Gly-Pro-Arg(NO₂)-Fca-OMe | 1416955-92-4

• 英文名称: Boc-Gly-Pro-Arg(NO₂)-Fca-OMe
• CAS: 1416955-92-4
• 化学式: C₃₀H₄₂FeN₈O₉
• 分子量: 714.559
• InChiKey: ZKZSFTBMUKHTCO-SZKOKKDDSA-N

计算性质

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反应信息

• 作为产物：
  描述：

  H-Arg(NO2)-Fc-OMe 、 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以30.6%的产率得到Boc-Gly-Pro-Arg(NO₂)-Fca-OMe
  参考文献：
  名称：

  Ferrocene tripeptide Gly-Pro-Arg conjugates: Synthesis and inhibitory effects on Alzheimer’s Aβ1–42 fibrillogenesis and Aβ-induced cytotoxicity in vitro

  摘要：

  Alzheimer's disease (AD) is the most common cause of dementia, and currently there is no clinical treatment to cure it or to halt its progression. Aggregation and fibril formation of beta-amyloid peptides (A beta) are central events in the pathogenesis of AD. Many efforts have been spent on the development of effective inhibitors to prevent A beta fibrillogenesis and cause disaggregation of preformed A beta fibrils. In this study, the conjugates of ferrocene and Gly-Pro-Arg (GPR) tripeptide, Boc-Gly-Pro-Arg(NO2)-Fca-OMe (4, GPR-Fca) and Fc-Gly-Pro-Arg-OMe (7, Fc-GPR) (Fc: ferrocene; Fca: ferrocene amino acid) were synthesized by HOBT/HBTU protocol in solution. These ferrocene GPR conjugates were employed to inhibit A beta(1-42) fibrillogenesis and to disaggregate preformed A beta fibrils. The inhibitory properties of ferrocene GPR conjugates on A beta(1-42) fibrillogenesis were evaluated by thioflavin T (ThT) fluorescence assay, and confirmed by atomic force microscopy (AFM) analysis. The interaction between the ferrocene GPR conjugates and A beta(1-42) was monitored by electrochemical means. Our results showed that both GPR and GPR-Fca can significantly inhibit the fibril formation of A beta(1-42), and cause disaggregation of the preformed fibrils. As expected, GPR-Fca shows stronger inhibitory effect on A beta(1-42) fibrillogenesis than that of its parent peptide GPR. In contrast, Fc-GPR shows no inhibitory effect on fibrillogenesis of A beta(1-42). Furthermore, GPR-Fca demonstrates significantly protection against A beta-induced cytotoxicity and exhibits high resistance to proteolysis and good lipophilicity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.030