二乙烯三胺三乙酸三氟乙酰胺三(叔-丁酯) | 180152-84-5

• 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
• 中文名称: 二乙烯三胺三乙酸三氟乙酰胺三(叔-丁酯)
• 英文名称: Diethylenetriaminetriacetic Acid Trifluoroacetamide Tri(tert-butyl Ester)
• 英文别名: tert-butyl 2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl-[2-[(2,2,2-trifluoroacetyl)amino]ethyl]amino]acetate
• CAS: 180152-84-5
• 化学式: C₂₄H₄₂F₃N₃O₇
• 分子量: 541.609
• InChiKey: FBVPJOYSURPZDJ-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿、二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  37
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  二乙烯三胺三乙酸三氟乙酰胺三(叔-丁酯) 在 palladium on activated charcoal 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 、 肼 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 9.5h， 生成 3,6,9-tris(2-(tert-butoxy)-2-oxoethyl)-13,13-dimethyl-11-oxo-12-oxa-3,6,9-triazatetradecan-1-oic acid
  参考文献：
  名称：

  Reassessment of Diethylenetriaminepentaacetic Acid (DTPA) as a Chelating Agent for Indium-111 Labeling of Polypeptides Using a Newly Synthesized Monoreactive DTPA Derivative

  摘要：

  Previous studies on indium-111 (In-111) labeling of polypeptides and peptides using cyclic diethylenetriaminepentaacetic dianhydride (cDTPA) as a bifunctional chelating agent (BCA) have indicated that DTPA might be a useful BCA for In-111 labeling of polypeptides at high specific activities when DTPA can be incorporated without inducing intra- or intermolecular cross-linking. To investigate this hypothesis, a monoreactive DTPA derivative with a maleimide group as the peptide binding site (MDTPA) was designed and synthesized. A monoclonal antibody (OST7, IgG(1)) was used as a model polypeptide, and conjugation of MDTPA with OST7, In-111 radiolabeling of MDTPA-OST7, and the stability of In-111-MDTPA-OST7 were investigated using cDTPA and benzyl-EDTA derivatives as references. SDS-PAGE analysis demonstrated that while cDTPA induced intramolecular cross-linking, no such undesirable side reactions were observed with MDTPA. MDTPA generated In-111-labeled OST7 with high radiochemical yields at higher specific activities than those produced using cDTPA and benzyl-EDTA derivatives as the BCAs. incubation of each In-111-labeled OST7 in human serum indicated that MDTPA generated In-111-labeled OST7 of much higher and a little lower stability than those derived from cDTPA and benzyl-EDTA derivatives, respectively. These findings indicated that the low in vivo stability of cDTPA-conjugated antibody reported previously is not attributable to low stability of In-111-DTPA but to formation of intramolecular cross-linking during cDTPA conjugation reactions. The present study also indicated that MDTPA and its precursor, the tetra-tert-butyl derivative of DTPA, would be useful BCAs for In-111 radiolabeling of polypeptides that have rapid blood clearance with high specific activities.

  DOI：

  10.1021/jm950949+
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 1-Trifluoroacetyl-1,4,7-triazaheptane 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 生成 二乙烯三胺三乙酸三氟乙酰胺三(叔-丁酯)
  参考文献：
  名称：

  Reassessment of Diethylenetriaminepentaacetic Acid (DTPA) as a Chelating Agent for Indium-111 Labeling of Polypeptides Using a Newly Synthesized Monoreactive DTPA Derivative

  摘要：

  Previous studies on indium-111 (In-111) labeling of polypeptides and peptides using cyclic diethylenetriaminepentaacetic dianhydride (cDTPA) as a bifunctional chelating agent (BCA) have indicated that DTPA might be a useful BCA for In-111 labeling of polypeptides at high specific activities when DTPA can be incorporated without inducing intra- or intermolecular cross-linking. To investigate this hypothesis, a monoreactive DTPA derivative with a maleimide group as the peptide binding site (MDTPA) was designed and synthesized. A monoclonal antibody (OST7, IgG(1)) was used as a model polypeptide, and conjugation of MDTPA with OST7, In-111 radiolabeling of MDTPA-OST7, and the stability of In-111-MDTPA-OST7 were investigated using cDTPA and benzyl-EDTA derivatives as references. SDS-PAGE analysis demonstrated that while cDTPA induced intramolecular cross-linking, no such undesirable side reactions were observed with MDTPA. MDTPA generated In-111-labeled OST7 with high radiochemical yields at higher specific activities than those produced using cDTPA and benzyl-EDTA derivatives as the BCAs. incubation of each In-111-labeled OST7 in human serum indicated that MDTPA generated In-111-labeled OST7 of much higher and a little lower stability than those derived from cDTPA and benzyl-EDTA derivatives, respectively. These findings indicated that the low in vivo stability of cDTPA-conjugated antibody reported previously is not attributable to low stability of In-111-DTPA but to formation of intramolecular cross-linking during cDTPA conjugation reactions. The present study also indicated that MDTPA and its precursor, the tetra-tert-butyl derivative of DTPA, would be useful BCAs for In-111 radiolabeling of polypeptides that have rapid blood clearance with high specific activities.

  DOI：

  10.1021/jm950949+

文献信息

• Reassessment of Diethylenetriaminepentaacetic Acid (DTPA) as a Chelating Agent for Indium-111 Labeling of Polypeptides Using a Newly Synthesized Monoreactive DTPA Derivative
  作者：Yasushi Arano、Takashi Uezono、Hiromichi Akizawa、Masahiro Ono、Kouji Wakisaka、Morio Nakayama、Harumi Sakahara、Junji Konishi、Akira Yokoyama

  DOI：10.1021/jm950949+

  日期：1996.1.1

  Previous studies on indium-111 (In-111) labeling of polypeptides and peptides using cyclic diethylenetriaminepentaacetic dianhydride (cDTPA) as a bifunctional chelating agent (BCA) have indicated that DTPA might be a useful BCA for In-111 labeling of polypeptides at high specific activities when DTPA can be incorporated without inducing intra- or intermolecular cross-linking. To investigate this hypothesis, a monoreactive DTPA derivative with a maleimide group as the peptide binding site (MDTPA) was designed and synthesized. A monoclonal antibody (OST7, IgG(1)) was used as a model polypeptide, and conjugation of MDTPA with OST7, In-111 radiolabeling of MDTPA-OST7, and the stability of In-111-MDTPA-OST7 were investigated using cDTPA and benzyl-EDTA derivatives as references. SDS-PAGE analysis demonstrated that while cDTPA induced intramolecular cross-linking, no such undesirable side reactions were observed with MDTPA. MDTPA generated In-111-labeled OST7 with high radiochemical yields at higher specific activities than those produced using cDTPA and benzyl-EDTA derivatives as the BCAs. incubation of each In-111-labeled OST7 in human serum indicated that MDTPA generated In-111-labeled OST7 of much higher and a little lower stability than those derived from cDTPA and benzyl-EDTA derivatives, respectively. These findings indicated that the low in vivo stability of cDTPA-conjugated antibody reported previously is not attributable to low stability of In-111-DTPA but to formation of intramolecular cross-linking during cDTPA conjugation reactions. The present study also indicated that MDTPA and its precursor, the tetra-tert-butyl derivative of DTPA, would be useful BCAs for In-111 radiolabeling of polypeptides that have rapid blood clearance with high specific activities.