5-[1,2]-dithiolan-3-yl-pentoic acid 2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 5-[1,2]-dithiolan-3-yl-pentoic acid 2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester
• 英文别名: 2-[2-[2-(2-Hydroxyethoxy)ethoxy]ethoxy]ethyl 5-(dithiolan-3-yl)pentanoate
• 化学式: C₁₆H₃₀O₆S₂
• 分子量: 382.543
• InChiKey: LRKVVPHZQGBRGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-[1,2]-dithiolan-3-yl-pentoic acid 2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以88%的产率得到6,8-dimercapto-octanoic acid 2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester
  参考文献：
  名称：

  Synthesis of Compact Multidentate Ligands to Prepare Stable Hydrophilic Quantum Dot Fluorophores

  摘要：

  We describe a simple and versatile scheme to prepare an array of heterofunctional multidentate ligands that permit strong and stable interactions with colloidal semiconductor nanocrystals (quantum dots, QDs) and render them soluble in aqueous environments. These ligands were synthesized by reacting various chain length poly(ethylene glycols) with thioctic acid, followed by ring opening of the dithiolane moiety, creating a bidentate thiol motif with enhanced affinity for CdSe-ZnS core-shell QDs. Functionalization with these ligands permits processability of the nanocrystals not only in aqueous but also in many other polar solvents. These ligands provide a straightforward means of preparing QDs that exhibit greater resistance to environmental changes, making them more amenable for use in live cell imaging and other biotechnological applications.

  DOI：

  10.1021/ja044031w
• 作为产物：
  描述：

  三缩四乙二醇 、 Thioctic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到5-[1,2]-dithiolan-3-yl-pentoic acid 2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester
  参考文献：
  名称：

  通过动态组合化学对纳米粒子进行局部模板驱动的功能化

  摘要：

  我们已经开发了一种使用基于亚胺的动态组合化学技术对金纳米颗粒进行局部功能化的方法。通过使用DNA模板，仅当纳米颗粒与模板分子发生相互作用时，才将胺接枝到醛官能化的纳米颗粒上。纳米颗粒的功能仅由DNA模板控制。只有能够与DNA相互作用的胺才结合到表面。有趣的是，即使我们的文库仅包含少量的简单胺，DNA序列也会影响它们与表面的附着。我们的方法为生物大分子的多价，基于纳米粒子的受体的合成开辟了新的机遇。

  DOI：

  10.1002/anie.201409667

文献信息

• [EN] ANTIOXIDANT CAMPTOTHECIN DERIVATIVES AND ANTIOXIDANT ANTINEOPLASTIC NANOSPHERES THEREOF<br/>[FR] DÉRIVÉS ANTIOXYDANTS DE LA CAMPTOTHÉCINE ET LEURS NANOSPHÈRES ANTIOXYDANTES ANTINÉOPLASIQUES
  申请人：CEDARS SINAI MEDICAL CENTER

  公开号：WO2010060098A1

  公开（公告）日：2010-05-27

  The present invention is directed to antioxidant derivatives of camptothecin and antioxidant derivatives of camptothecin analogs and the preparation of nanometer-sized camptothecin prodrugs. Methods of synthesizing the antioxidant derivatives of camptothecin and antioxidant derivatives of camptothecin analogs, spontaneous emulsification or nanoprecipitation thereof to produce antioxidant camptothecin nanosphere prodrugs and their use in treating cancerous diseases are also provided. A further aspect of this invention is the use of these antioxidant camptothecin nanosphere prodrugs for the preparation of delivery devices of other pharmaceuticals and/or drugs.

  本发明涉及喜树碱的抗氧化衍生物、喜树碱类似物的抗氧化衍生物以及纳米级喜树碱前药的制备。还提供了合成喜树碱的抗氧化衍生物和喜树碱类似物的抗氧化衍生物的方法，以及通过自发乳化或纳米沉淀制备抗氧化喜树碱纳米球前药，并将其用于治疗癌症疾病的方法。本发明的另一个方面是利用这些抗氧化喜树碱纳米球前药制备其他药物的输送装置。
• Oxidative stimuli-responsive nanoprodrug of camptothecin kills glioblastoma cells
  作者：Bong-Seop Lee、Aruna K. Nalla、Ilana R. Stock、Talia C. Shear、Keith L. Black、John S. Yu

  DOI：10.1016/j.bmcl.2010.06.144

  日期：2010.9

  camptothecin prodrug was synthesized using tetraethylene glycol spacer linked via carbonate bond to camptothecin and via ester bond to α-lipoic acid. The nanoprodrug was prepared through the spontaneous emulsification mechanism using the mixture of camptothecin prodrug and α-tocopherol which served as a structural matrix. The nanoprodrug was activated readily by porcine liver esterase and, with a much slower rate

  这项研究的目的是制备和表征喜树碱的纳米级前药（nanoprodrug）。喜树碱前药是使用四甘醇间隔基合成的，所述四甘醇间隔基通过碳酸酯键与喜树碱连接，并通过酯键与α-硫辛酸连接。通过喜树碱前药和α-生育酚的混合物作为结构基质，通过自发乳化机理制备了纳米前药。猪肝酯酶可以很容易地激活纳米前药，而水解降解可以很慢地激活纳米前药。长期保存后，喜树碱前药的α-硫辛酸部分逐渐被氧化，而不会丧失结构完整性和治疗功效。有趣的是，在氧化之前水解活化作用可以忽略不计，但在α-硫辛酸部分氧化后明显加速，这表明前药具有氧化刺激响应活性。研究发现喜树碱纳米前药对U87-MG胶质瘤细胞的增殖具有明显的抑制作用20个nM中的50个。
• Synthesis of cationic quantum dots via a two-step ligand exchange process
  作者：Yi-Cheun Yeh、Debabrata Patra、Bo Yan、Krishnendu Saha、Oscar R. Miranda、Chae Kyu Kim、Vincent M. Rotello

  DOI：10.1039/c0cc04975a

  日期：——

  A new class of quaternary ammonium derivatives has been used to synthesize cationic CdSe/ZnS quantum dots with exceptional stability in water as well as in biological media.

  一类新的季铵盐衍生物已用于合成在水中及生物介质中具有出色稳定性的带正电荷的CdSe/ZnS量子点。
• [EN] NANOMETER-SIZED PRODRUGS OF NSAIDS<br/>[FR] PROMÉDICAMENTS DE DIMENSION NANOMÉTRIQUE DE NSAIDS
  申请人：CEDARS SINAI MEDICAL CENTER

  公开号：WO2009148698A1

  公开（公告）日：2009-12-10

  The present invention describes nanoprodrugs of non-steroidal anti-inflammatory drug (NSAIDs) and nanoprodrugs of α-lipoic acid-containing and NSAIDs. These nanoprodrugs have antioxidant properties and stimuli-responsiveness, which can be used to treat various disease conditions.

  本发明描述了非甾体抗炎药（NSAIDs）的纳米前药和含α-硫辛酸和NSAIDs的纳米前药。这些纳米前药具有抗氧化性能和刺激响应性，可用于治疗各种疾病情况。
• [EN] ANTIOXIDANT, NEUROPROTECTIVE AND ANTINEOPLASTIC NANOPARTICLES COMPRISING A THERAPEUTIC AGENT ON AN AMPHIPHILIC SPACER OR AN AMPHIPHILIC POLYMER<br/>[FR] NANOPARTICULES ANTIOXYDANTES, NEUROPROTECTRICES ET ANTINÉOPLASIQUES COMPRENANT UN AGENT THÉRAPEUTIQUE SUR UN ESPACEUR AMPHIPHILE OU UN POLYMÈRE AMPHIPHILE
  申请人：CEDARS SINAI MEDICAL CENTER

  公开号：WO2013016696A1

  公开（公告）日：2013-01-31

  This invention relates to antioxidant, neuroprotective and antineoplastic nanoparticles comprising a therapeutic agent on an amphiphilic spacer or an amphiphilic polymer. Methods of synthesizing the antioxidant derivatives of camptothecin and antioxidant derivatives of camptothecin analogs, NSAIDs and statins, spontaneous emulsification or nanoprecipitation thereof to produce antioxidant, neuroprotective and anti-neoplastic nanoparticles comprising a therapeutic agent on an amphiphilic spacer or an amphiphilic polymer and their use in treating cancerous diseases are also provided. A further aspect of this invention is the use of these neuroprotective and anti-neoplastic nanoparticles for the preparation of delivery devices of other pharmaceuticals and/or drugs.

  本发明涉及抗氧化剂、神经保护剂和抗肿瘤纳米粒子，其包括具有治疗剂的两性亲脂间隔物或两性亲脂聚合物。还提供了合成伯氨替芬的抗氧化剂衍生物和伯氨替芬类似物、NSAIDs和他汀类药物的抗氧化剂衍生物的方法，以及通过自发乳化或纳米沉淀制备这些抗氧化、神经保护和抗肿瘤纳米粒子，其包括具有治疗剂的两性亲脂间隔物或两性亲脂聚合物，并且它们在治疗癌症疾病中的应用。本发明的另一个方面是利用这些神经保护和抗肿瘤纳米粒子制备其他药物和/或药物的输送装置。