3,6,9,15-四氮杂双环[9.3.1]PENTADECA-1(15),11,13-三烯-4-S-(4-异硫氰酸根合苄基))-3,6,9-三乙酸 | 949147-44-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 3,6,9,15-四氮杂双环[9.3.1]PENTADECA-1(15),11,13-三烯-4-S-(4-异硫氰酸根合苄基))-3,6,9-三乙酸
• 英文名称: 2,2',2''-((4S)-4-(4-isothiocyanatobenzyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-3,6,9-triyl)triacetic acid
• 英文别名: p-SCN-Bn-pcta；2-[(4S)-3,9-bis(carboxymethyl)-4-[(4-isothiocyanatophenyl)methyl]-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(14),11(15),12-trien-6-yl]acetic acid
• CAS: 949147-44-8
• 化学式: C₂₅H₂₉N₅O₆S
• 分子量: 527.601
• InChiKey: FSOBASOXWBKMSC-QFIPXVFZSA-N

物化性质

• 沸点：
  773.6±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  179
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3,6,9,15-四氮杂双环[9.3.1]PENTADECA-1(15),11,13-三烯-4-S-(4-异硫氰酸根合苄基))-3,6,9-三乙酸 、 (3S,7S,22S)-26-amino-5,13,20-trioxo-4,6,12,21-tetraazahexacosane-1,3,7,22-tetracarboxylic acid 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以23%的产率得到9,16,24-trioxo-1-thioxo-1-((4-(((4S)-3,6,9-tris-(carboxymethyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1-(14),12-dien-4-yl)methyl)phenyl)amino)-2,8,17,23,25-pentaazaoctacosane-7,22,26,28-tetracarboxylic acid
  参考文献：
  名称：

  ⁶⁴Cu-Labeled Inhibitors of Prostate-Specific Membrane Antigen for PET Imaging of Prostate Cancer

  摘要：

  Prostate-specific membrane antigen (PSMA) is a well-recognized target for identification and therapy of a variety of cancers. Here we report five (64)Cu-labeled inhibitors of PSMA, [(64)Cu]3-7, which are based on the lysine-glutamate urea scaffold and utilize a variety of macrocyclic chelators, namely NOTA(3), PCTA(4), Oxo-DO3A(5), CB-TE2A(6), and DOTA(7), in an effort to determine which provides the most suitable pharmacokinetics for in vivo PET imaging. [(64)Cu]3-7 were prepared in high radiochemical yield (60-90%) and purity (>95%). Positron emission tomography (PET) imaging studies of [(64)Cu]3-7 revealed specific accumulation in PSMA-expressing xenografts (PSMA+ PC3 PIP) relative to isogenic control tumor (PSMA- PC3 flu) and background tissue. The favorable kinetics and high image contrast provided by CB-TE2A chelated [(64)Cu]6 suggest it as the most promising among the candidates tested. That could be due to the higher stability of [(64)Cu]CB-TE2A as compared with [(64)Cu]NOTA, [(64)Cu]PCTA, [(64)Cu]Oxo-DO3A, and [(64)Cu]DOTA chelates in vivo.

  DOI：

  10.1021/jm401921j
• 作为产物：
  描述：

  (S)-2,2',2''-(4-(4-aminobenzyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-3,6,9-triyl)triacetic acid 、 硫光气 以 氯仿 、 水 为溶剂， 生成 3,6,9,15-四氮杂双环[9.3.1]PENTADECA-1(15),11,13-三烯-4-S-(4-异硫氰酸根合苄基))-3,6,9-三乙酸
  参考文献：
  名称：

  WO2007/104135

  摘要：

  公开号：

文献信息

• [EN] CHELATED PSMA INHIBITORS<br/>[FR] INHIBITEURS CHÉLATÉS DU PSMA
  申请人：CANCER TARGETED TECHNOLOGY LLC

  公开号：WO2012174136A1

  公开（公告）日：2012-12-20

  Compounds as defined herein are provided which are useful in (1) diagnostic methods for detecting and/or identifying cells presenting PSMA; (2) compositions comprising a compound of the invention together with a pharmaceutically acceptable diluent; and (3) methods for imaging prostate cancer cells.

  本文定义的化合物可用于：（1）用于检测和/或鉴定表达PSMA的细胞的诊断方法；（2）包含本发明化合物的与药用稀释剂一起的组合物；以及（3）用于成像前列腺癌细胞的方法。
• BIFUNCTIONAL POLYAZAMACROCYCLIC CHELATING AGENTS
  申请人：Kovacs Zoltan

  公开号：US20120276001A1

  公开（公告）日：2012-11-01

  A bifunctional polyazamacrocyclic chelating agent of the formula (I): wherein: and the variables A, L, Q, Q 1 , X, Y, Z, Z 1 , m, n and r are as defined in the description of the present application. Also described is a complex of the above chelating agent to an ion of a metal ion, such as an ion of 90 Y, 111 In or 177 Lu; a conjugate of the complex covalently attached to a biological carrier; and a pharmaceutical composition containing the conjugate. A method of therapeutic treatment of a mammal involving administration of the pharmaceutical composition is also described.

  一种具有以下式子（I）的双功能聚合胺大环螯合剂： 其中：变量A、L、Q、Q1、X、Y、Z、Z1、m、n和r的定义如本申请说明书中所定义。本文还描述了上述螯合剂与金属离子（如90Y、111In或177Lu的离子）的配合物，以及与生物载体共价连接的配合物；以及含有该共价连接物的药物组合物。还描述了一种治疗哺乳动物的方法，涉及给予该药物组合物的治疗。
• Chelated PSMA Inhibitors
  申请人：Berkman Clifford

  公开号：US20140241985A1

  公开（公告）日：2014-08-28

  Compounds as defined herein are provided which are useful in (1) diagnostic methods for detecting and/or identifying cells presenting PSMA; (2) compositions comprising a compound of the invention together with a pharmaceutically acceptable diluent; and (3) methods for imaging prostate cancer cells.

  本文提供了化合物，其用于：(1)检测和/或鉴定呈现PSMA的细胞的诊断方法；(2)包含本发明化合物和药学可接受稀释剂的组合物；以及(3)成像前列腺癌细胞的方法。
• Bifunctional Polyazamacrocyclic Chelating Agents
  申请人：Kovaks Zoltan

  公开号：US20090202521A1

  公开（公告）日：2009-08-13

  A bifunctional polyazamacrocyclic chelating agent of the formula (I): wherein: and the variables A, L, Q, Q 1 , X, Y, Z, Z 1 , m, n and r are as defined in the description of the present application. Also described is a complex of the above chelating agent to an ion of a metal ion, such as an ion of 90 Y, 111 Li or 177 Lu; a conjugate of the complex covalently attached to a biological carrier; and a pharmaceutical composition containing the conjugate. A method of therapeutic treatment of a mammal involving administration of the pharmaceutical composition is also described.

  一种具有以下式子(I)的双功能聚合物氮杂大环螯合剂：其中：变量A、L、Q、Q1、X、Y、Z、Z1、m、n和r如本申请说明书所定义。还描述了上述螯合剂与金属离子的复合物，例如90Y、111Li或177Lu离子；复合物共价结合到生物载体的结合物；以及含有该结合物的药物组合物。还描述了一种治疗哺乳动物的方法，涉及给予药物组合物的治疗。
• Chelated PSMA inhibitors
  申请人：Cancer Targeted Technology

  公开号：US10166301B2

  公开（公告）日：2019-01-01

  Compounds as defined herein are provided which are useful in (1) diagnostic methods for detecting and/or identifying cells presenting PSMA; (2) compositions comprising a compound of the invention together with a pharmaceutically acceptable diluent; and (3) methods for imaging prostate cancer cells.

  本文所定义的化合物可用于：(1) 检测和/或识别呈现 PSMA 的细胞的诊断方法；(2) 由本发明化合物和药学上可接受的稀释剂组成的组合物；(3) 前列腺癌细胞成像方法。