1-(3-aza-8-carboxy-2-oxooctyl)-4,7,10-tris((1,1-dimethylethoxy)carbonylmethyl)-1,4,7,10-tetraazacyclododecane benzyl ester | 878750-06-2

• 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: 1-(3-aza-8-carboxy-2-oxooctyl)-4,7,10-tris((1,1-dimethylethoxy)carbonylmethyl)-1,4,7,10-tetraazacyclododecane benzyl ester
• 英文别名: 1-(3-aza-2,9-dioxo-10-oxa-11-phenyl-undecyl)-4,7,10-tris(tert-butyloxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane；Benzyl 6-[[2-[4,7,10-tris[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetyl]amino]hexanoate
• CAS: 878750-06-2
• 化学式: C₄₁H₆₉N₅O₉
• 分子量: 776.027
• InChiKey: OQBIPNHBMXDGAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  55
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1-(3-aza-8-carboxy-2-oxooctyl)-4,7,10-tris((1,1-dimethylethoxy)carbonylmethyl)-1,4,7,10-tetraazacyclododecane benzyl ester 在 palladium on activated charcoal phosphate buffer 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 1-((11-S)-3,10-diaza-13-carboxamido-11-carboxy-2,9-dioxotridecyl)-4,7,10-tris((1,1-dimethylethoxy)carbonylmethyl)-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  In Vitro and in Vivo Magnetic Resonance Detection of Tumor Cells by Targeting Glutamine Transporters with Gd-Based Probes

  摘要：

  The glutamine transporting system is up-regulated in tumor cells because cell proliferation requires the uptake of large quantities of glutamine. It has been found that the paramagnetic magnetic resonance imaging (MRI) reporter Gd-DOTAMA-C-6-Gln, where the glutamine residue is covalently bound to the Gd chelate through a C-6 spacer, accumulates in tumor cells both "in vitro" and "in vivo" experiments. The observation that the relaxivity of cellular pellets does not increase with the increase in the amounts of entrapped Gd chelate is taken as an indication that the internalization has occurred through receptor mediated endocytosis. The iv administration of Gd-DOTAMA-C-6-Gln allowed the MRI visualization of tumor masses in A/J mice grafted with the murine neuroblastoma cell line Neuro-2a and in Her2/neu transgenic mice developing multiple mammary carcinoma, respectively.

  DOI：

  10.1021/jm0601093
• 作为产物：
  描述：

  benzyl 6-aminohexanoate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 10.67h， 生成 1-(3-aza-8-carboxy-2-oxooctyl)-4,7,10-tris((1,1-dimethylethoxy)carbonylmethyl)-1,4,7,10-tetraazacyclododecane benzyl ester
  参考文献：
  名称：

  In Vitro and in Vivo Magnetic Resonance Detection of Tumor Cells by Targeting Glutamine Transporters with Gd-Based Probes

  摘要：

  The glutamine transporting system is up-regulated in tumor cells because cell proliferation requires the uptake of large quantities of glutamine. It has been found that the paramagnetic magnetic resonance imaging (MRI) reporter Gd-DOTAMA-C-6-Gln, where the glutamine residue is covalently bound to the Gd chelate through a C-6 spacer, accumulates in tumor cells both "in vitro" and "in vivo" experiments. The observation that the relaxivity of cellular pellets does not increase with the increase in the amounts of entrapped Gd chelate is taken as an indication that the internalization has occurred through receptor mediated endocytosis. The iv administration of Gd-DOTAMA-C-6-Gln allowed the MRI visualization of tumor masses in A/J mice grafted with the murine neuroblastoma cell line Neuro-2a and in Her2/neu transgenic mice developing multiple mammary carcinoma, respectively.

  DOI：

  10.1021/jm0601093

文献信息

• [EN] PARAMAGNETIC METAL POLYAMINO COMPLEXES FOR MRI VISUALIZATION OF INTERNALIZED POLYNUCLEOTIDES<br/>[FR] COMPLEXES METALLIQUES PARAMAGNETIQUES POUR LA VISUALISATION EN IRM DE POLYNUCLEOTIDES INTERNALISES
  申请人：BRACCO IMAGING SPA

  公开号：WO2006027244A3

  公开（公告）日：2006-11-30
• In Vitro and in Vivo Magnetic Resonance Detection of Tumor Cells by Targeting Glutamine Transporters with Gd-Based Probes
  作者：Geninatti Crich、Claudia Cabella、Alessandro Barge、Simona Belfiore、Cristina Ghirelli、Luciano Lattuada、Stefania Lanzardo、Armando Mortillaro、Lorenzo Tei、Massimo Visigalli、Guido Forni、Silvio Aime

  DOI：10.1021/jm0601093

  日期：2006.8.1

  The glutamine transporting system is up-regulated in tumor cells because cell proliferation requires the uptake of large quantities of glutamine. It has been found that the paramagnetic magnetic resonance imaging (MRI) reporter Gd-DOTAMA-C-6-Gln, where the glutamine residue is covalently bound to the Gd chelate through a C-6 spacer, accumulates in tumor cells both "in vitro" and "in vivo" experiments. The observation that the relaxivity of cellular pellets does not increase with the increase in the amounts of entrapped Gd chelate is taken as an indication that the internalization has occurred through receptor mediated endocytosis. The iv administration of Gd-DOTAMA-C-6-Gln allowed the MRI visualization of tumor masses in A/J mice grafted with the murine neuroblastoma cell line Neuro-2a and in Her2/neu transgenic mice developing multiple mammary carcinoma, respectively.