2,2′,2″-(10-(6-aminohexyl)-1,4,7,10-tetraazacyclododeca-1,4,7-triyl)triacetic acid | 1255709-56-8

• 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: 2,2′,2″-(10-(6-aminohexyl)-1,4,7,10-tetraazacyclododeca-1,4,7-triyl)triacetic acid
• 英文别名: 2-[4-(6-Aminohexyl)-7,10-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid；2-[4-(6-aminohexyl)-7,10-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
• CAS: 1255709-56-8
• 化学式: C₂₀H₃₉N₅O₆
• 分子量: 445.56
• InChiKey: HTALLMGBVVLSKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.4
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  IRDye800CW-NHS ester 、 2,2′,2″-(10-(6-aminohexyl)-1,4,7,10-tetraazacyclododeca-1,4,7-triyl)triacetic acid 在 碳酸氢钠 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 以80%的产率得到
  参考文献：
  名称：

  Multimodal Chelation Platform for Near-Infrared Fluorescence/Nuclear Imaging

  摘要：

  Dual-labeled compounds containing nuclear and near-infrared fluorescence contrast have the potential to molecularly guide surgical resection of cancer by extending whole-body diagnostic imaging findings into the surgical suite. To simplify the dual labeling process for antibody-based agents, we designed a multimodality chelation (MMC) scaffold which combined a radiometal chelating agent and fluorescent dye into a single moiety. Three dye-derivatized MMC compounds were synthesized and radiolabeled. The IRDye 800CW conjugate, 4, had favorable optical properties and showed rapid clearance in vivo. Using 4, an epithelial cell adhesion molecule (EpCAM) targeting MMC-immunoconjugate was prepared and dual-labeled with Cu-64. In vitro binding activity was confirmed after MMC conjugation. Multimodal imaging studies showed accumulation of Cu-64-7 compared to nontargeted Cu-64-4 in a prostate cancer model. Further evaluation in different EpCAM-expressing cell lines is warranted as well as application of the MMC dual labeling approach with other monoclonal antibodies.

  DOI：

  10.1021/jm300906g
• 作为产物：
  描述：

  tert-butyl 2,2′,2″-(10-(N-(tert-butoxycarbonyl)-6-aminohexyl)-1,4,7,10-tetraazacyclododeca-1,4,7-triyl)-triacetate 在 盐酸 作用下， 反应 4.0h， 以118 mg的产率得到2,2′,2″-(10-(6-aminohexyl)-1,4,7,10-tetraazacyclododeca-1,4,7-triyl)triacetic acid
  参考文献：
  名称：

  Multimodal Chelation Platform for Near-Infrared Fluorescence/Nuclear Imaging

  摘要：

  Dual-labeled compounds containing nuclear and near-infrared fluorescence contrast have the potential to molecularly guide surgical resection of cancer by extending whole-body diagnostic imaging findings into the surgical suite. To simplify the dual labeling process for antibody-based agents, we designed a multimodality chelation (MMC) scaffold which combined a radiometal chelating agent and fluorescent dye into a single moiety. Three dye-derivatized MMC compounds were synthesized and radiolabeled. The IRDye 800CW conjugate, 4, had favorable optical properties and showed rapid clearance in vivo. Using 4, an epithelial cell adhesion molecule (EpCAM) targeting MMC-immunoconjugate was prepared and dual-labeled with Cu-64. In vitro binding activity was confirmed after MMC conjugation. Multimodal imaging studies showed accumulation of Cu-64-7 compared to nontargeted Cu-64-4 in a prostate cancer model. Further evaluation in different EpCAM-expressing cell lines is warranted as well as application of the MMC dual labeling approach with other monoclonal antibodies.

  DOI：

  10.1021/jm300906g

文献信息

• Multimodal Chelation Platform for Near-Infrared Fluorescence/Nuclear Imaging
  作者：Sukhen C. Ghosh、Pradip Ghosh、Nathaniel Wilganowski、Holly Robinson、Mary A. Hall、Gabriel Dickinson、Ken L. Pinkston、Barrett R. Harvey、Eva M. Sevick-Muraca、Ali Azhdarinia

  DOI：10.1021/jm300906g

  日期：2013.1.24

  Dual-labeled compounds containing nuclear and near-infrared fluorescence contrast have the potential to molecularly guide surgical resection of cancer by extending whole-body diagnostic imaging findings into the surgical suite. To simplify the dual labeling process for antibody-based agents, we designed a multimodality chelation (MMC) scaffold which combined a radiometal chelating agent and fluorescent dye into a single moiety. Three dye-derivatized MMC compounds were synthesized and radiolabeled. The IRDye 800CW conjugate, 4, had favorable optical properties and showed rapid clearance in vivo. Using 4, an epithelial cell adhesion molecule (EpCAM) targeting MMC-immunoconjugate was prepared and dual-labeled with Cu-64. In vitro binding activity was confirmed after MMC conjugation. Multimodal imaging studies showed accumulation of Cu-64-7 compared to nontargeted Cu-64-4 in a prostate cancer model. Further evaluation in different EpCAM-expressing cell lines is warranted as well as application of the MMC dual labeling approach with other monoclonal antibodies.