doxorubicin hydrochloride | 62777-61-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: doxorubicin hydrochloride
• 英文别名: (7S,9S)-7-[(2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
• CAS: 62777-61-1
• 化学式: C₂₇H₂₉NO₁₁*ClH
• 分子量: 579.988
• InChiKey: MWWSFMDVAYGXBV-AMSIYOEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  206
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  、 doxorubicin hydrochloride 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 以0.045 g的产率得到
  参考文献：
  名称：

  Synthesis of chemically functionalized superparamagnetic nanoparticles as delivery vectors for chemotherapeutic drugs

  摘要：

  Superparamagnetic iron oxide nanoparticles (SPIONs) are in clinical use for disease detection by MRI. A major advancement would be to link therapeutic drugs to SPIONs in order to achieve targeted drug delivery combined with detection. In the present work, we studied the possibility of developing a versatile synthesis protocol to hierarchically construct drug-functionalized-SPIONs as potential anti-cancer agents. Our model biocompatible SPIONs consisted of an iron oxide core (9-10 nm diameter) coated with polyvinylalcohols (PVA/aminoPVA), which can be internalized by cancer cells, depending on the positive charges at their surface. To develop drug-functionalized-aminoPVA-SPIONs as vectors for drug delivery, we first designed and synthesized bifunctional linkers of varied length and chemical composition to which the anti-cancer drugs 5-fluorouridine or doxorubicin were attached as biologically labile esters or peptides, respectively. These functionalized linkers were in turn coupled to aminoPVA by amide linkages before preparing the drug-functionalized-SPIONs that were characterized and evaluated as anti-cancer agents using human melanoma cells in culture. The 5-fluorouridine-SPIONs with an optimized ester linker were taken up by cells and proved to be efficient anti-tumor agents. While the doxorubicin-SPIONs linked with a Gly-Phe-Leu-Gly tetrapeptide were cleaved by lysosomal enzymes, they exhibited poor uptake by human melanoma cells in culture. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.051

文献信息

• Intracellularly Actuated Quantum Dot–Peptide–Doxorubicin Nanobioconjugates for Controlled Drug Delivery via the Endocytic Pathway
  作者：Ajmeeta Sangtani、Eleonora Petryayeva、Miao Wu、Kimihiro Susumu、Eunkeu Oh、Alan L. Huston、Guillermo Lasarte-Aragones、Igor L. Medintz、W. Russ Algar、James B. Delehanty

  DOI：10.1021/acs.bioconjchem.7b00658

  日期：2018.1.17

  Nanoparticle (NP)-mediated drug delivery (NMDD) has emerged as a novel method to overcome the limitations of traditional systemic delivery of therapeutics, including the controlled release of the NP-associated drug cargo. Currently, our most advanced understanding of how to control NP-associated cargos is in the context of soft nanoparticles (e.g., liposomes), but less is known about controlling the

  纳米粒子（NP）介导的药物传递（NMDD）已经成为克服传统系统疗法的局限性的新方法，其中包括与NP相关的药物货物的受控释放。当前，我们对如何控制与NP相关的货物的最先进的理解是在软纳米颗粒（例如脂质体）的背景下进行的，但对于控制货物从硬NP（例如金NP）表面的释放知之甚少。在这里，我们采用半导体量子点（QD）作为原型硬NP平台，并使用细胞内触发的致动来实现时空控制药物释放和调节药物功效。与QD结合的是两种肽：（1）促进共轭物进入内吞途径的细胞穿透肽（CPP），以及（2）通过三个不同的键（酯，二硫键和）与阿霉素（DOX）缀合的展示肽酶促裂解，还原条件和低pH值。QD- [肽-DOX] -CPP复合物的形成是由自组装驱动的，它可以控制与QD结合的每种肽的比率以及最终传递给细胞的药物剂量。Förster共振能量转移测定法证实了QD-肽复合物的成功组装和键的功能性。共聚焦显微镜用于观察QD- [肽-DOX]