Boc-Tyr-c[Cys-Gly-Phe-NH-NH<-Phe<-Gly-<-Cys]<-Tyr-Boc | 873684-56-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Boc-Tyr-c[Cys-Gly-Phe-NH-NH<-Phe<-Gly-<-Cys]<-Tyr-Boc
• CAS: 873684-56-1
• 化学式: C₅₆H₇₀N₁₀O₁₄S₂
• 分子量: 1171.36
• InChiKey: PGPYVOBQJYYZSY-FEHIJEOVSA-N

反应信息

• 作为反应物：
  描述：

  Boc-Tyr-c[Cys-Gly-Phe-NH-NH<-Phe<-Gly-<-Cys]<-Tyr-Boc 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Tyr-c[D-Cys-Gly-Phe-NH-NH<-Phe<-Gly<-D-Cys]<-Tyr bis(trifluoroacetic acid salt)
  参考文献：
  名称：

  Synthesis and biological activity of the first cyclic biphalin analogues

  摘要：

  Biphalin is a linear octapeptide with strong opioid activity. Its structure is based on two identical sequences derived from enkephalins joined C-terminal to C-terminal by an hydrazide bridge (Tyr-D-Ala-Gly-Phe-NH-NH <- Phe <- Gly <- D-Ala <- Tyr). In this study we present the design, synthesis, and biological evaluation of the first cyclic biphalin analogues. D-Alanine residues in positions 2, 2' of the parent peptide were replaced by D- and L-cysteine and an intramolecular disulfide bond between the cysteine thiol groups was introduced. We obtained two cyclic analogues with quite different biological profiles. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.080
• 作为产物：
  描述：

  Boc-Tyr-Cys(Acm)-Gly-Phe-NH-NH<-Phe<-Gly<-Cys(Acm)<-Tyr-Boc 在 碘 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以40%的产率得到Boc-Tyr-c[Cys-Gly-Phe-NH-NH<-Phe<-Gly-<-Cys]<-Tyr-Boc
  参考文献：
  名称：

  Synthesis and biological activity of the first cyclic biphalin analogues

  摘要：

  Biphalin is a linear octapeptide with strong opioid activity. Its structure is based on two identical sequences derived from enkephalins joined C-terminal to C-terminal by an hydrazide bridge (Tyr-D-Ala-Gly-Phe-NH-NH <- Phe <- Gly <- D-Ala <- Tyr). In this study we present the design, synthesis, and biological evaluation of the first cyclic biphalin analogues. D-Alanine residues in positions 2, 2' of the parent peptide were replaced by D- and L-cysteine and an intramolecular disulfide bond between the cysteine thiol groups was introduced. We obtained two cyclic analogues with quite different biological profiles. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.080

文献信息

• Developing Cyclic Opioid Analogues: Fluorescently Labeled Bioconjugates of Biphalin
  作者：Azzurra Stefanucci、Marilisa Pia Dimmito、Gabriela Molnar、John M. Streicher、Ettore Novellino、Gokhan Zengin、Adriano Mollica

  DOI：10.1021/acsmedchemlett.9b00569

  日期：2020.5.14

  pivotal importance in medicinal chemistry due to their potential applications as therapeutic agents to improve the targeting of specific diseases, decrease toxicity, or control drug release. In this work we achieved the synthesis and characterization of three novel opioid peptides fluorescently labeled, analogues of cyclic biphalin derivatives, namely 1D, 1C, and 2C. Among them, compound 1D, containing

  生物共轭物的开发在药物化学中具有至关重要的意义，因为它们作为治疗剂的潜在应用可改善特定疾病的靶向性，降低毒性或控制药物释放。在这项工作中，我们实现了荧光标记的三种新型阿片样肽的合成和表征，它们是环状双phalin衍生物的类似物，即1D，1C和2C。其中，包含丹磺酰基马来酰亚胺基序的化合物1D对δ阿片受体（DOR）表现出优异的结合亲和力和功能性。1D还显示了300至700 nm的强荧光发射光谱。对于靶向DOR所需的医学和生物学应用（包括体内成像），以及作为荧光探针设计的先导，这些功能可能非常理想。