2-[(3R,6S,12S,15R)-12-[3-(diaminomethylideneamino)propyl]-3-[(4-hydroxy-3-iodophenyl)methyl]-2,5,8,11,14-pentaoxo-17-oxa-1,4,7,10,13-pentazabicyclo[13.4.0]nonadecan-6-yl]acetic acid | 1380422-43-4

• 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: 2-[(3R,6S,12S,15R)-12-[3-(diaminomethylideneamino)propyl]-3-[(4-hydroxy-3-iodophenyl)methyl]-2,5,8,11,14-pentaoxo-17-oxa-1,4,7,10,13-pentazabicyclo[13.4.0]nonadecan-6-yl]acetic acid
• CAS: 1380422-43-4
• 化学式: C₂₆H₃₅IN₈O₉
• 分子量: 730.517
• InChiKey: LPOXWPIIMACJCX-WNRNVDISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  268
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 三异丙基硅烷 、 chloramine-T 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 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-) 、 三氟乙酸 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.33h， 生成 2-[(3R,6S,12S,15R)-12-[3-(diaminomethylideneamino)propyl]-3-[(4-hydroxy-3-iodophenyl)methyl]-2,5,8,11,14-pentaoxo-17-oxa-1,4,7,10,13-pentazabicyclo[13.4.0]nonadecan-6-yl]acetic acid
  参考文献：
  名称：

  ¹²⁵I-Radiolabeled Morpholine-Containing Arginine–Glycine–Aspartate (RGD) Ligand of α_vβ₃ Integrin As a Molecular Imaging Probe for Angiogenesis

  摘要：

  In this paper, using a hybrid small-animal Micro SPECT/CT imaging system, we report that a new I-125-Cilengitide-like RGD-cyclopentapeptide, containing D-morpholine-3-carboxylic acid, interacts in vivo with alpha(v)beta(3) integrin expressed by melanoma cells. Images clearly show that the I-125-compound has the capacity to monitor the growth of a melanoma xenograft. Indeed, retention of the labeled ligand in the tumor mass has a good tumor/background ratio, and a significant reduction of its uptake was observed after injection of unlabeled ligand. These results suggest that the use of I-125-labeled morpholine-based RGD-cyclopentapeptides targeting alpha(v)beta(3) positive tumors may play a role in future therapeutic strategies.

  DOI：

  10.1021/jm2016232

文献信息

• ¹²⁵I-Radiolabeled Morpholine-Containing Arginine–Glycine–Aspartate (RGD) Ligand of α_vβ₃ Integrin As a Molecular Imaging Probe for Angiogenesis
  作者：Francesca Bianchini、Nicoletta Cini、Andrea Trabocchi、Anna Bottoncetti、Silvia Raspanti、Eleonora Vanzi、Gloria Menchi、Antonio Guarna、Alberto Pupi、Lido Calorini

  DOI：10.1021/jm2016232

  日期：2012.6.14

  In this paper, using a hybrid small-animal Micro SPECT/CT imaging system, we report that a new I-125-Cilengitide-like RGD-cyclopentapeptide, containing D-morpholine-3-carboxylic acid, interacts in vivo with alpha(v)beta(3) integrin expressed by melanoma cells. Images clearly show that the I-125-compound has the capacity to monitor the growth of a melanoma xenograft. Indeed, retention of the labeled ligand in the tumor mass has a good tumor/background ratio, and a significant reduction of its uptake was observed after injection of unlabeled ligand. These results suggest that the use of I-125-labeled morpholine-based RGD-cyclopentapeptides targeting alpha(v)beta(3) positive tumors may play a role in future therapeutic strategies.