6-aza-5,9-dioxo-9-(1,2-didehydrodibenzo[b,f]azocin-5(6H)-yl)nonanoic acid succinimidyl ester | 1393350-27-0

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 6-aza-5,9-dioxo-9-(1,2-didehydrodibenzo[b,f]azocin-5(6H)-yl)nonanoic acid succinimidyl ester
• 英文别名: 4-dibenzocyclooctynamidobutanoic acid N-hydroxysuccinimidyl ester；dibenzocyclooctyne-N-hydroxysuccinimidyl ester；ADIBO N-succinimidyl ester；DBCO-NHS ester 3；(2,5-dioxopyrrolidin-1-yl) 5-(2-azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-5-oxopentanoate
• CAS: 1393350-27-0
• 化学式: C₂₄H₂₀N₂O₅
• 分子量: 416.433
• InChiKey: CFQHVJJWCDJMLI-UHFFFAOYSA-N

物化性质

• 沸点：
  679.2±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  5

制备方法与用途

生物活性

DBCO-NHS ester 3 (Compound 12) 是一种用于制备抗体偶联药物 (ADC) 的可降解 linker。DBCO-NHS ester 3 是一种二苯基环辛酮 (DBCO) 衍生物，通过 MeOND 和 DIBAC 的羧酸部分被 N-羟基琥珀酰亚胺活化而获得的。

靶点

Cleavable

反应信息

• 作为反应物：
  描述：

  6-aza-5,9-dioxo-9-(1,2-didehydrodibenzo[b,f]azocin-5(6H)-yl)nonanoic acid succinimidyl ester 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  [EN] CYCLAM BASED COMPOUNDS, THEIR CONJUGATES, CO-ORDINATION COMPOUNDS, PHARMACEUTICAL COMPOSITION CONTAINING THEREOF, METHOD OF PREPARATION AND USE THEREOF
  [FR] COMPOSÉS À BASE DE CYCLAME, LEURS CONJUGUÉS, COMPOSÉS DE COORDINATION, COMPOSITION PHARMACEUTIQUE LES CONTENANT, PROCÉDÉ DE PRÉPARATION ET UTILISATION ASSOCIÉS

  摘要：

  基于环戊胺的化合物、其共轭物、配位化合物、含有其的药物组合物、制备方法及使用方法。本发明涉及一般式(I)的基于环戊胺的化合物、这些化合物与共轭基的共轭物、它们的配位化合物、靶向共轭物、基于环戊胺的化合物的制备方法、制备基于环戊胺的化合物的中间产物、含有它们的药物制剂及其用途。

  公开号：

  WO2017084645A1

文献信息

• [EN] SULFONE LINKERS<br/>[FR] COUPLEURS AU SULFONE
  申请人：PROLYNX LLC

  公开号：WO2013036857A1

  公开（公告）日：2013-03-14

  Sulfone linkers which couple drugs to carriers of various types are described. These linkers permit the release of the drug over time in a controlled manner. The release occurs through beta-elimination, and does not require enzymatic cleavage. Products of the linkers with both drugs and macromolecules and methods of using them are described as well.

  研究描述了将药物与各种载体耦合的砜键连接剂。这些连接剂允许药物以受控方式随时间释放。释放是通过β-消除而发生的，并不需要酶解。还描述了连接剂与药物和大分子的产物以及它们的使用方法。
• F-18 Labeled RGD Probes Based on Bioorthogonal Strain-Promoted Click Reaction for PET Imaging
  作者：Hye Lan Kim、Kalme Sachin、Hyeon Jin Jeong、Wonsil Choi、Hyun Soo Lee、Dong Wook Kim

  DOI：10.1021/ml500464f

  日期：2015.4.9

  A series of fluorine-substituted monomeric and dimeric cRGD peptide derivatives, such as cRGD-ADIBOT-F (ADIBOT = azadibenzocyclooctatriazole), di-cRGD-ADIBOT-F, cRGD-PEG(5)-ADIBOT-F, and di-cRGD-PEG(5)-ADIBOT-F, were prepared by strain-promoted alkyne azide cycloaddition (SPAAC) reaction of the corresponding aza-dibenzocyclooctyne (ADIBO) substituted peptides with a fluorinated azide 3. Among these cRGD derivatives, di-cRGD-PEG(5)-ADIBOT-F had the highest binding affinity in a competitive binding assay compared to other derivatives and even the original cRGDyk. On the basis of the in vitro study results, di-cRGD-PEG(5)-ADIBOT-F-18 was prepared from a SPAAC reaction with F-18-labeled azide and subsequent chemo-orthogonal scavenger-assisted separation without high performance liquid chromatography (HPLC) purification in 92% decay-corrected radiochemical yield (dcRCY) with high specific activity for further in vivo positron emission tomography (PET) imaging study. In vivo PET imaging study and biodistribution data showed that this radiotracer allowed successful visualization of tumors with good tumor-to-background contrast and significantly higher tumor uptake compared to other major organs.