cyclo[C(S-)YNPTTYQMC(S-)] | 1174416-59-1

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: cyclo[C(S-)YNPTTYQMC(S-)]
• 英文别名: cyclic-CYNPTTYQMC；H-Cys(1)-Tyr-Asn-Pro-Thr-Thr-Tyr-Gln-Met-Cys(1)-OH；(3S,6S,9R,14R,17S,20S,23S,26S,29S,32S)-9-amino-3-(2-amino-2-oxoethyl)-20-(3-amino-3-oxopropyl)-26,29-bis[(1R)-1-hydroxyethyl]-6,23-bis[(4-hydroxyphenyl)methyl]-17-(2-methylsulfanylethyl)-2,5,8,16,19,22,25,28,31-nonaoxo-11,12-dithia-1,4,7,15,18,21,24,27,30-nonazabicyclo[30.3.0]pentatriacontane-14-carboxylic acid
• CAS: 1174416-59-1
• 化学式: C₅₁H₇₂N₁₂O₁₇S₃
• 分子量: 1221.4
• InChiKey: ZNCMXWOQRFXVST-FBTLNAABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  83
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  559
• 氢给体数：
  16
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  CYNPTTYQMC 在 碳酸氢铵 作用下， 以 水 为溶剂， 反应 3.0h， 生成 cyclo[C(S-)YNPTTYQMC(S-)]
  参考文献：
  名称：

  Inhibitory effect of a dimerization-arm-mimetic peptide on EGF receptor activation

  摘要：

  A cyclic decapeptide was chemically synthesized that mimics the loop structure of a beta-hairpin arm of the EGF receptor, which is highly involved in receptor dimerization upon activation by ligand binding. This peptide was revealed to reduce dimer formation of the receptor in a detergent-solubilized extract of epidermoid carcinoma A431 cells and to inhibit receptor autophosphorylation at less than 10 mu M in the intact cells. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.080

文献信息

• Functional evaluation of fluorescein-labeled derivatives of a peptide inhibitor of the EGF receptor dimerization
  作者：Kei Toyama、Takaaki Mizuguchi、Wataru Nomura、Hirokazu Tamamura

  DOI：10.1016/j.bmc.2016.05.026

  日期：2016.8

  carcinoma cells, the fluorescence of peptide 2 was localized inside some vesicles. Treatment of intact cells by peptide 1 in combination with peptide 2 decreased the fluorescence intensity significantly compared to treatment with only peptide 2. These results indicate that peptide 2 competes with peptide 1 for binding to the cellular surface. Six derivatives of peptide 2, in which constituent amino acids

  环十肽（1， 已经开发出了一种作用于EGF受体的细胞外区域，防止其二聚化的β-内化酶。肽2，将其标记在肽的N末端荧光素1，是基于结构-活性关系的研究合成。肽2基本上保留了肽1对受体自身磷酸化的抑制活性。共聚焦显微镜研究表明，在癌细胞中，肽2的荧光位于某些囊泡中。与仅使用肽处理相比，通过肽1与肽2组合处理完整细胞可显着降低荧光强度2。这些结果表明肽2与肽1竞争结合至细胞表面。合成了肽2的六个衍生物，其中除了两个半胱氨酸和脯氨酸外，其组成氨基酸是随机的，并用于处理细胞。肽6和9在细胞中显示出最高的荧光强度。从EGF受体自磷酸化分析的结果来看，这两种衍生物被证明比肽2具有更高的抑制活性，因此，这将是有用的递送肽和荧光探针，以发现针对EGF受体的新抑制剂。肽6和9 是EGF受体抑制剂的有希望的潜在客户。
• Inhibitory effect of a dimerization-arm-mimetic peptide on EGF receptor activation
  作者：Takaaki Mizuguchi、Hiromasa Uchimura、Taeko Kakizawa、Tooru Kimura、Shigeyuki Yokoyama、Yoshiaki Kiso、Kazuki Saito

  DOI：10.1016/j.bmcl.2009.04.080

  日期：2009.6

  A cyclic decapeptide was chemically synthesized that mimics the loop structure of a beta-hairpin arm of the EGF receptor, which is highly involved in receptor dimerization upon activation by ligand binding. This peptide was revealed to reduce dimer formation of the receptor in a detergent-solubilized extract of epidermoid carcinoma A431 cells and to inhibit receptor autophosphorylation at less than 10 mu M in the intact cells. (C) 2009 Elsevier Ltd. All rights reserved.