tri-tert-butyl 2,2',2''-(10-(17-(1,3-dioxoisoindolin-2-yl)-3,6,9,12,15-pentaoxaheptadecyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate | 1422957-54-7

• 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: tri-tert-butyl 2,2',2''-(10-(17-(1,3-dioxoisoindolin-2-yl)-3,6,9,12,15-pentaoxaheptadecyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate
• CAS: 1422957-54-7
• 化学式: C₄₆H₇₇N₅O₁₃
• 分子量: 908.143
• InChiKey: FWIUTYAUEOCAHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  64.0
• 可旋转键数：
  24.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  175.39
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  tri-tert-butyl 2,2',2''-(10-(17-(1,3-dioxoisoindolin-2-yl)-3,6,9,12,15-pentaoxaheptadecyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate 在 肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以96%的产率得到tri-tert-butyl 2,2',2''-(10-(17-amino-3,6,9,12,15-pentaoxaheptadecyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate
  参考文献：
  名称：

  cRGD Peptide-Conjugated Icosahedral closo-B₁₂^2- Core Carrying Multiple Gd³⁺-DOTA Chelates for α_vβ₃ Integrin-Targeted Tumor Imaging (MRI)

  摘要：

  A vertex-differentiated icosahedral closo-B-12(2-) core was utilized to construct a alpha(v)beta(3) integrin receptor-targeted (via cRGD peptide) high payload MRI contrast agent (CA-12) carrying 11 copies of Gd3+-DOTA chelates attached to the closo-B-12(2-) surface via suitable linkers. The resulting polyfunctional MRI contrast agent possessed a higher relaxivity value per-Gd compared to Omniscan, a small molecular contrast agent commonly used in clinical settings. The alpha(v)beta(3) integrin receptor specificity of CA-12 was confirmed via in vitro cellular binding experiments and in vivo MRI of mice bearing human PC-3 prostate cancer xenografts. Integrin alpha(v)beta(3)-positive MDA-MB-231 cells exhibited 300% higher uptake of CA-12 than alpha(v)beta(3)-negative T47D cells. Serial T1-weighted MRI showed superior contrast enhancement of tumors by CA-12 compared to both a nontargeted 12-fold Gd3+-DOTA closomer control (CA-7) and Omniscan. Contrast enhancement by CA-12 persisted for 4 h postinjection, and subsequent enhancement of kidney tissue indicated a renal elimination route similar to Omniscan. No toxic effects of CA-12 were apparent in any mice for up to 24 h postinjection. Post-mortem ICP-OES analysis at 24 h detected no residual Gd in any of the tissue samples analyzed.

  DOI：

  10.1021/ic302340c
• 作为产物：
  描述：

  六甘醇 在 potassium hydrogencarbonate 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 53.0h， 生成 tri-tert-butyl 2,2',2''-(10-(17-(1,3-dioxoisoindolin-2-yl)-3,6,9,12,15-pentaoxaheptadecyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate
  参考文献：
  名称：

  cRGD Peptide-Conjugated Icosahedral closo-B₁₂^2- Core Carrying Multiple Gd³⁺-DOTA Chelates for α_vβ₃ Integrin-Targeted Tumor Imaging (MRI)

  摘要：

  A vertex-differentiated icosahedral closo-B-12(2-) core was utilized to construct a alpha(v)beta(3) integrin receptor-targeted (via cRGD peptide) high payload MRI contrast agent (CA-12) carrying 11 copies of Gd3+-DOTA chelates attached to the closo-B-12(2-) surface via suitable linkers. The resulting polyfunctional MRI contrast agent possessed a higher relaxivity value per-Gd compared to Omniscan, a small molecular contrast agent commonly used in clinical settings. The alpha(v)beta(3) integrin receptor specificity of CA-12 was confirmed via in vitro cellular binding experiments and in vivo MRI of mice bearing human PC-3 prostate cancer xenografts. Integrin alpha(v)beta(3)-positive MDA-MB-231 cells exhibited 300% higher uptake of CA-12 than alpha(v)beta(3)-negative T47D cells. Serial T1-weighted MRI showed superior contrast enhancement of tumors by CA-12 compared to both a nontargeted 12-fold Gd3+-DOTA closomer control (CA-7) and Omniscan. Contrast enhancement by CA-12 persisted for 4 h postinjection, and subsequent enhancement of kidney tissue indicated a renal elimination route similar to Omniscan. No toxic effects of CA-12 were apparent in any mice for up to 24 h postinjection. Post-mortem ICP-OES analysis at 24 h detected no residual Gd in any of the tissue samples analyzed.

  DOI：

  10.1021/ic302340c