succinimidyl 6-[2-(4-dimethylamino)benzaldehydrazono]nicotinate | 186305-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: succinimidyl 6-[2-(4-dimethylamino)benzaldehydrazono]nicotinate
• CAS: 186305-06-6
• 化学式: C₁₉H₁₉N₅O₄
• 分子量: 381.391
• InChiKey: JWESIOCIQIBRBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  104.2
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  succinimidyl 6-[2-(4-dimethylamino)benzaldehydrazono]nicotinate 、 pteroyl-Lys 在 吡啶 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以65%的产率得到pteroyl-lys-HYNIC
  参考文献：
  名称：

  The synthesis of pteroyl-lys conjugates and its application as Technetium-99m labeled radiotracer for folate receptor-positive tumor targeting

  摘要：

  Aiming to develop a new Tc-99m-labeled folate derivative for FR-positive tumor imaging, a simpler method has been established to synthesize the folate-drug conjugates with free alpha-carboxyl group. In this study, the conjugate pteroyl-lys-HYNIC was synthesized and labeled with Tc-99m using tricine and TPPTS as co-ligands. The radiochemical purity of the final complex Tc-99m(HYNIC-lys-pteroyl)(tricine/TPPTS), 5 was high (>98%), and it remained stable in saline and plasma over 6 h after preparation. The biologic evaluation results showed that the Tc-99m labeled pteroyl-lys conjugate was able to specifically target the FR-positive tumor cells and tissues both in vitro and in vivo, highlighting its potential as an effective folate receptor targeted agent for tumor imaging. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.014
• 作为产物：
  描述：

  6-氯烟酸 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 succinimidyl 6-[2-(4-dimethylamino)benzaldehydrazono]nicotinate
  参考文献：
  名称：

  （99m）Tc标记的二聚叶酸的FR合成与评价。

  摘要：

  叶酸受体（FR）在多种人类肿瘤中均过表达。在我们的研究中，多聚体概念用于通过点击反应合成二聚叶酸衍生物。使用三辛酸和三苯基膦-3,3'，3″-三磺酸盐（TPPTS）作为大肠菌素（（99m）Tc-HYNIC-D₁-FA2），用（99m）Tc标记新型叶酸衍生物（HYNIC-D₁-FA2）并对其潜在的FR靶向药物的体外理化性质，离体生物分布和体内micro-SPECT / CT成像进行了评估。它是一种具有高结合亲和力（IC50 = 19.06 nM）的亲水性化合物（log P = -2.52±0.13）。在具有KB肿瘤的KB小鼠中的生物分布表明，（99m）Tc-HYNIC-D₁-FA2在所有时间点都对FR过表达的肿瘤和肾脏具有高摄取，在阻断研究中，当用游离FA阻断时，两者均明显受到抑制。从体内的微型SPECT / CT成像结果，在KB荷瘤小鼠中观察到良好的（99m）Tc-HYNIC-DFA-FA

  DOI：

  10.3390/molecules21060817

文献信息

• Synthesis and preliminary evaluation of a ^99m Tc-labeled folate-PAMAM dendrimer for FR imaging
  作者：Manli Song、Zhide Guo、Mengna Gao、Changrong Shi、Duo Xu、Linyi You、Xiaowei Wu、Xinhui Su、Rongqiang Zhuang、Weimin Pan、Ting Liu、Xianzhong Zhang

  DOI：10.1111/cbdd.12899

  日期：2017.5

  Folate receptor is an ideal target for tumor‐specific diagnostic and therapeutic. The aim of this study was to synthesize 99mTc‐labeled folate‐polyamidoamine dendrimer modified with 2‐hydrazinonicotinic acid (99mTc‐HP3FA) for FR imaging. The 99mTc‐HP3FA conjugate was prepared using N‐tris‐(hydroxymethyl)‐methylglycine and trisodium triphenylphosphine‐3,3′,3″‐trisulfonate as coligands. Physicochemical properties, in vitro cell uptake study, and in vivo micro‐single‐photon emission computed tomography/CT imaging were performed. The radiolabeled 99mTc‐HP3FA conjugate was prepared with high radiolabeling yield, good stability, and water solubility (logP = −1.70 ± 0.21). In cell uptake study, the radiolabeled conjugate showed high uptakes in the FR‐abundant KB cells and could be blocked significantly by excess folic acid. The 7721 cells which served as control group substantially had no uptakes. The results of micro‐single‐photon emission computed tomography/CT imaging exhibited that high accumulation of activity was found in FR‐overexpressed KB tumor, and the tumor‐to‐muscle ratio was approximately 25.78, while, using free FA as inhibitor, the uptakes of 99mTc‐HP3FA in KB tumor and kidney were obviously inhibited. In summary, a new radiocompound was synthesized successfully with specific FR targeting ability. The feasibility of 99mTc‐HP3FA for early diagnosis of FR‐positive tumors with non‐invasive single‐photon emission computed tomography imaging was demonstrated and the possibility of imaging‐guided drug delivery based on multifunctional polyamidoamine will be studied in the future.
• Rational Design and Comparison of Novel 99mTc-Labeled FAPI Dimers for Visualization of Multiple Tumor Types
  作者：Lingxin Meng、Jianyang Fang、Jingru Zhang、Huifeng Li、Dongsheng Xia、Rongqiang Zhuang、Haojun Chen、Jinxiong Huang、Yesen Li、Xianzhong Zhang、Zhide Guo

  DOI：10.1021/acs.jmedchem.4c00772

  日期：2024.5.23