rhodamine B (acrylate 2-hydroxyethyl)ester | 1156509-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: rhodamine B (acrylate 2-hydroxyethyl)ester
• 英文别名: rhodamine B (2-hydroxyethyl acrylate)ester；[6-(Diethylamino)-9-[2-(2-prop-2-enoyloxyethoxycarbonyl)phenyl]xanthen-3-ylidene]-diethylazanium;chloride；[6-(diethylamino)-9-[2-(2-prop-2-enoyloxyethoxycarbonyl)phenyl]xanthen-3-ylidene]-diethylazanium;chloride
• CAS: 1156509-18-0
• 化学式: C₃₃H₃₇N₂O₅*Cl
• 分子量: 577.12
• InChiKey: VWJAETOFOTWVBX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  罗丹明B 在 氯化亚砜 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 32.0h， 生成 rhodamine B (acrylate 2-hydroxyethyl)ester
  参考文献：
  名称：

  A cancer-targetable copolymer containing tyrosine segments for labeling radioactive halogens

  摘要：

  A series of cancer-targetable copolymers containing rhodamine and tyrosine segments were synthesized and further labeled with isotope I-125. Copolymers with different molecular weights (PRTH-1, PRTH-2 and PRTH-3) formed aggregates in water with average diameters of 66 nm, 191 nm and 137 nm, respectively. The cancer cell targeting properties of the copolymers were investigated by comparing BEL-7402 liver cancer cells and L-02 human normal liver cells. The results indicate that their targeting properties are related to the average diameters of the PRTH copolymers that self-assembled in water. PRTH-2 copolymers were selected as having the best targeting properties for cancer cells. The in vivo study of HepA mouse models based on single-photon emission computed tomography (SPECT) also showed good tumor-targeting properties of PRTH-2 labeled with I-125. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.reactfunctpolym.2010.12.009

文献信息

• Light-responsive amphiphilic copolymer coated nanoparticles as nanocarriers and real-time monitors for controlled drug release
  作者：Qingjian Xing、Najun Li、Dongyun Chen、Wenwei Sha、Yang Jiao、Xiuxiu Qi、Qingfeng Xu、Jianmei Lu

  DOI：10.1039/c3tb21269f

  日期：——

  Herein, light-responsive nanocarriers based on hollow mesoporous silica (HMS) nanoparticles modified with spiropyran-containing light-responsive copolymer (PRMS-FA) were fabricated via a simple self-assembly process. HMS modified with long-chain hydrocarbon octadecyltrimethoxysilane was an ideal base material owing to its good biocompatibility and drug capability. The spiropyran-containing amphiphilic copolymer could shift its hydrophilic–hydrophobic balance to become hydrophilic upon UV (λ = 365 nm) irradiation and then break away from the hydrophobic surface of the HMS core, followed by the uncaging and release of the pre-loaded anticancer drug. Simultaneously, the fluorescence resonance energy transfer (FRET) process based on the structural transformation of PRMS-FA was observed, which could act as a real-time monitor for the light-controlled drug release. Our model experiments in vitro tested and verified that this composite nanocarrier has good biocompatibility, active tumour targeting to the folate receptor over-expressed in tumour cells, is non-toxic to normal cells and that light-controlled drug release with real-time monitoring can be achieved.

  本文通过简单的自组装工艺，制备了基于含螺吡喃光响应共聚物（PRMS-FA）修饰的中空介孔二氧化硅（HMS）纳米颗粒的光响应纳米载体。长链碳氢化合物十八烷基三甲氧基硅烷修饰的 HMS 具有良好的生物相容性和药物功能，是一种理想的基础材料。在紫外线（λ = 365 nm）照射下，含有螺吡喃的两亲共聚物可改变其亲水-疏水平衡，变得亲水，然后脱离 HMS 内核的疏水表面，释放出预载的抗癌药物。与此同时，我们还观察到了基于 PRMS-FA 结构转变的荧光共振能量转移（FRET）过程，该过程可作为光控药物释放的实时监测器。我们的体外模型实验测试并验证了这种复合纳米载体具有良好的生物相容性、对肿瘤细胞中过度表达的叶酸受体具有积极的肿瘤靶向性、对正常细胞无毒，并且可以实现实时监测的光控药物释放。