fluorescein adamantylthiourea | 188007-55-8

• 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: fluorescein adamantylthiourea
• CAS: 188007-55-8
• 化学式: C₃₁H₂₈N₂O₅S
• 分子量: 540.64
• InChiKey: YWHQWUVHYNGUJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  39.0
• 可旋转键数：
  2.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  100.05
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  异硫氰酸荧光素酯 、 金刚烷胺 以 四氢呋喃 为溶剂， 以62 %的产率得到fluorescein adamantylthiourea
  参考文献：
  名称：

  中链脂质缀合促进细胞渗透性和生物活性

  摘要：

  大多数生物活性分子作用于膜蛋白或细胞内靶标，因此需要进入或穿过生物膜。天然产物通常表现出脂质修饰，以促进关键的分子-膜相互作用，并且在许多情况下，在去除脂质基团后，它们的生物活性显着降低。然而，尽管小分子的脂质缀合在自然界中很重要，但在化学生物学和药物化学中并不常用，并且这种缀合的效果尚未得到系统研究。为了了解天然产物中脂质的组成，我们对“天然产物脂质组”进行了化学信息学表征。根据该分析，脂化天然产物主要含有饱和中链脂质（MCL），其明显短于膜和脂化蛋白质中发现的长链脂质（LCL）。为了研究此类修饰在探针设计中的有用性，我们系统地探讨了脂质缀合对五种不同小分子化学型的影响，并发现渗透性、细胞保留、亚细胞定位和生物活性可以根据所用脂质尾的类型进行显着调节。我们证明 MCL 缀合可以使分子具有细胞渗透性并调节其生物活性。在所有探索的化学型中，与 LCL 缀合物相比，MCL 缀合物始终表现出优异的吸收或生物活性，并且与短链脂质

  DOI：

  10.1021/jacs.2c07833

文献信息

• A switchable polymer brush system for antifouling and controlled detection
  作者：Serkan Demirci、Selin Kinali-Demirci、Shan Jiang

  DOI：10.1039/c7cc00193b

  日期：——

  A stimuli-responsive polymer brush system is designed to switch on and off surface functionality and prevent functional groups from fouling by grafting together two polymer brushes with precisely controlled lengths....

  刺激响应的聚合物刷系统旨在通过将两个长度精确控制的聚合物刷接枝在一起来打开和关闭表面功能，并防止官能团结垢。
• Modular Assembly of Host–Guest Metal–Phenolic Networks Using Macrocyclic Building Blocks
  作者：Shuaijun Pan、Rui Guo、Nadja Bertleff‐Zieschang、Shanshan Li、Quinn A. Besford、Qi‐Zhi Zhong、Gyeongwon Yun、Yunti Zhang、Francesca Cavalieri、Yi Ju、Eirini Goudeli、Joseph J. Richardson、Frank Caruso

  DOI：10.1002/anie.201912296

  日期：2020.1.2

  are conjugated to catechol or galloyl groups and subsequently used as components for the assembly of functional MPNs. The assembled cyclodextrin-based MPNs are highly permeable (even to high molecular weight polymers: 250-500 kDa), yet they specifically and noncovalently interact with various functional guests (including small molecules, polymers, and carbon nanomaterials), allowing for modular and

  界面性能的操纵对于高性能涂料的开发具有广泛的意义。金属酚醛网络（MPN）是一类新兴的响应性，粘附性材料。在此，主客体化学与MPN集成在一起以调节其表面化学和界面特性。大环环糊精（宿主）与邻苯二酚或没食子酰基缀合，随后用作组装功能性MPN的组分。组装的基于环糊精的MPN具有高渗透性（甚至对于高分子量聚合物：250-500 kDa），但它们能与各种功能性客体（包括小分子，聚合物和碳纳米材料）特异性且非共价地相互作用，从而允许模块化和可逆性控制界面性质。具体来说，
• Supramolecular nanoparticle carriers self-assembled from cyclodextrin- and adamantane-functionalized polyacrylates for tumor-targeted drug delivery
  作者：Chung Yen Ang、Si Yu Tan、Xiaoling Wang、Quan Zhang、Majad Khan、Linyi Bai、Subramanian Tamil Selvan、Xing Ma、Liangliang Zhu、Kim Truc Nguyen、Nguan Soon Tan、Yanli Zhao

  DOI：10.1039/c3tb21325k

  日期：——

  The advancement of nanobiotechnology has led to the development of various techniques for addressing target-specific drug delivery issues. In this article, we successfully developed a supramolecular self-assembly approach for the fabrication of polyacrylate-based nanoparticles with simultaneous loading of the anticancer drug doxorubicin (DOX) for targeted delivery towards cancer treatment in vitro and in vivo. Two types of polyacrylates functionalized with adamantane and β-cyclodextrin respectively could self-assemble to form supramolecular nanoparticles through strong host–guest complexation between adamantane and β-cyclodextrin. Folic acid was incorporated within the supramolecular nanoparticles in order to impart the targeting specificity towards selected cancerous cell lines, namely MDA-MB231 and B16-F10. The as-synthesized supramolecular nanoparticles were fully characterized by several techniques, revealing an average nanoparticle size of 35 nm in diameter, which is small enough for excellent blood circulation. The cytotoxicity studies indicate that the supramolecular nanoparticles without drug loading were non-cytotoxic under the concentrations measured, while DOX-loaded supramolecular nanoparticles showed significant cytotoxicity. In order to investigate the targeting specificity of DOX-loaded supramolecular nanoparticles towards the cancerous cells, a healthy cell line model HEK293 was employed for carrying out the comparison studies. Due to the presence of the targeting ligand, experimental results demonstrate that the supramolecular nanoparticles were highly specific for targeting the cancerous cells, but not for HEK293 cells. After the in vitro investigations, the in vivo drug delivery study using DOX-loaded supramolecular nanoparticles was performed. Tumor-bearing nude mice were treated with DOX-loaded supramolecular nanoparticles, and the analysis results indicate that DOX-loaded supramolecular nanoparticles have the capability to enhance the therapeutic effects of DOX for effectively inhibiting the tumor growth. Thus, the self-assembled polymeric nanoparticles exhibit a highly promising potential to serve as drug carriers for targeted drug delivery towards improved cancer treatment.

  纳米生物技术的进步导致了解决特定目标药物输送问题的各种技术的发展。在本文中，我们成功开发了一种超分子自组装方法，用于制造基于聚丙烯酸酯的纳米颗粒，同时负载抗癌药物阿霉素（DOX），用于体外和体内癌症治疗的靶向递送。两种分别用金刚烷和β-环糊精功能化的聚丙烯酸酯可以通过金刚烷和β-环糊精之间的强主客体络合自组装形成超分子纳米粒子。将叶酸掺入超分子纳米颗粒中，以赋予针对选定癌细胞系（即 MDA-MB231 和 B16-F10）的靶向特异性。通过多种技术对合成的超分子纳米颗粒进行了全面表征，显示平均纳米颗粒尺寸为直径 35 nm，足够小，可以实现良好的血液循环。细胞毒性研究表明，未负载药物的超分子纳米颗粒在测量浓度下无细胞毒性，而负载DOX的超分子纳米颗粒则表现出显着的细胞毒性。为了研究负载DOX的超分子纳米粒子对癌细胞的靶向特异性，采用健康细胞系模型HEK293进行比较研究。由于靶向配体的存在，实验结果表明超分子纳米颗粒对于靶向癌细胞具有高度特异性，但对于 HEK293 细胞则不然。在体外研究之后，进行了使用负载DOX的超分子纳米颗粒的体内药物递送研究。用负载DOX的超分子纳米颗粒治疗荷瘤裸鼠，分析结果表明负载DOX的超分子纳米颗粒能够增强DOX的治疗效果，有效抑制肿瘤生长。因此，自组装聚合物纳米颗粒表现出作为药物载体用于靶向药物递送以改善癌症治疗的非常有前途的潜力。