(3S)-3-[[2-[[(2S)-5-(diaminomethylideneamino)-2-[[2-(1,2,5-dithiazepan-5-yl)acetyl]amino]pentanoyl]amino]acetyl]amino]-4-oxo-4-(2-sulfanylethylamino)butanoic acid | 1187459-26-2

• 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: (3S)-3-[[2-[[(2S)-5-(diaminomethylideneamino)-2-[[2-(1,2,5-dithiazepan-5-yl)acetyl]amino]pentanoyl]amino]acetyl]amino]-4-oxo-4-(2-sulfanylethylamino)butanoic acid
• CAS: 1187459-26-2
• 化学式: C₂₀H₃₆N₈O₆S₃
• 分子量: 580.754
• InChiKey: QRZPNBYMEWEFPP-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  273
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (3S)-3-[[2-[[(2S)-5-(diaminomethylideneamino)-2-[[2-(1,2,5-dithiazepan-5-yl)acetyl]amino]pentanoyl]amino]acetyl]amino]-4-oxo-4-(2-sulfanylethylamino)butanoic acid 在 ⁽¹²⁵⁾I-echistatin 、 α(V)β(3) integrin receptor 作用下， 以100%的产率得到
  参考文献：
  名称：

  Synthesis and biochemical evaluation of a cyclic RGD oxorhenium complex as new ligand of αVβ3 integrin

  摘要：

  We report the design of a new ligand of integrins that might be used for the molecular imaging of tumor neoangiogenesis. For this purpose, we designed a modified RGD tripeptide bearing a N-terminal N-bis(thioethyl)glycinate (NS2) motif and a thioethyl moiety at the C-terminus. Simultaneous coordination of an oxorhenium core by the NS2 and thioethyl moieties led to peptide cyclization and gave the corresponding monomers 13a and b (major isomer) resulting from the syn/anti-isomerism, along with dimers' species 16a and b. Cyclometallated peptide 13b showed the most promising activity with an IC50 of 86 nM for integrin alpha(V)beta(3) whereas it binds integrin a(IIb)beta(3) with an affinity lower by an order of magnitude. Labeling with [(99)mTc]oxotechnetium gluconate led exclusively to complex 17, the equivalent of compound 13b, which displayed satisfactory stabilities in mice plasma and towards glutathione. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.02.022
• 作为产物：
  描述：

  Fmoc-Asp(OAll)-Pol 、 2-(1,2,5-dithiazepan-5-yl)acetic acid 、 Fmoc-甘氨酸 、 Fmoc-Pbf-L-精氨酸 、 2-(tritylthio)ethan-1-ammonium trifluoroacetate 在 吗啉 、 四(三苯基膦)钯 、 溶剂黄146 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (3S)-3-[[2-[[(2S)-5-(diaminomethylideneamino)-2-[[2-(1,2,5-dithiazepan-5-yl)acetyl]amino]pentanoyl]amino]acetyl]amino]-4-oxo-4-(2-sulfanylethylamino)butanoic acid
  参考文献：
  名称：

  Synthesis and biochemical evaluation of a cyclic RGD oxorhenium complex as new ligand of αVβ3 integrin

  摘要：

  We report the design of a new ligand of integrins that might be used for the molecular imaging of tumor neoangiogenesis. For this purpose, we designed a modified RGD tripeptide bearing a N-terminal N-bis(thioethyl)glycinate (NS2) motif and a thioethyl moiety at the C-terminus. Simultaneous coordination of an oxorhenium core by the NS2 and thioethyl moieties led to peptide cyclization and gave the corresponding monomers 13a and b (major isomer) resulting from the syn/anti-isomerism, along with dimers' species 16a and b. Cyclometallated peptide 13b showed the most promising activity with an IC50 of 86 nM for integrin alpha(V)beta(3) whereas it binds integrin a(IIb)beta(3) with an affinity lower by an order of magnitude. Labeling with [(99)mTc]oxotechnetium gluconate led exclusively to complex 17, the equivalent of compound 13b, which displayed satisfactory stabilities in mice plasma and towards glutathione. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.02.022