2'-acryloyl taxol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2'-acryloyl taxol
• 英文别名: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-prop-2-enoyloxypropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• 化学式: C₅₀H₅₃NO₁₅
• 分子量: 907.969
• InChiKey: QNDHJDORFPMDMO-MJZMOBIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  66
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  227
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2'-acryloyl taxol 在 sodium metabisulfite 作用下， 以 水 、 异丙醇 为溶剂， 反应 16.0h， 以84%的产率得到sodium;3-[(1S,2R)-1-benzamido-3-[[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl]oxy]-3-oxo-1-phenylpropan-2-yl]oxy-3-oxopropane-1-sulfonate
  参考文献：
  名称：

  Sulfonates-PMMA nanoparticles conjugates: A versatile system for multimodal application

  摘要：

  We report herein the viability of a novel nanoparticles (NPs) conjugated system, namely the attachment, based on ionic and hydrophobic interactions, of different sulfonated organic salts to positively charged poly(methylmethacrylate) (PMMA)-based core-shell nanoparticles (EA0) having an high density of ammonium groups on their shells. In this context three different applications of the sulfonates@EA0 systems have been described. In detail, their ability as cytotoxic drugs and pro-drugs carriers was evaluated in vitro on NCI-H460 cell line and in vivo against human ovarian carcinoma IGROV-1 cells. Besides, 8-hydroxypyrene-1,3,6-trisulfonic acid, trisodium salt (HPTS) was chosen for NPs loading, and its internalization as bioimaging probe was evaluated on Hep G2 cells. Overall, the available data support the interest for these PMMA NPs@sulfonates systems as a promising formulation for theranostic applications. In vivo biological data strongly support the potential value of these core-shell NPs as delivery system for negatively charged drugs or biologically active molecules. Additionally, we have demonstrated the ability of these PMMA core-shell nanoparticles to act as efficient carriers of fluorophores. In principle, thanks to the high PMMA NPs external charge density, sequential and very easy post-loading of different sulfonates is achievable, thus allowing the preparation of nanocarriers either with bi-modal drug delivery behaviour or as theranostic systems. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.023
• 作为产物：
  描述：

  紫杉醇 、 丙烯酸 在 4-二甲氨基吡啶 、 scandium tris(trifluoromethanesulfonate) 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以96%的产率得到2'-acryloyl taxol
  参考文献：
  名称：

  Sulfonates-PMMA nanoparticles conjugates: A versatile system for multimodal application

  摘要：

  We report herein the viability of a novel nanoparticles (NPs) conjugated system, namely the attachment, based on ionic and hydrophobic interactions, of different sulfonated organic salts to positively charged poly(methylmethacrylate) (PMMA)-based core-shell nanoparticles (EA0) having an high density of ammonium groups on their shells. In this context three different applications of the sulfonates@EA0 systems have been described. In detail, their ability as cytotoxic drugs and pro-drugs carriers was evaluated in vitro on NCI-H460 cell line and in vivo against human ovarian carcinoma IGROV-1 cells. Besides, 8-hydroxypyrene-1,3,6-trisulfonic acid, trisodium salt (HPTS) was chosen for NPs loading, and its internalization as bioimaging probe was evaluated on Hep G2 cells. Overall, the available data support the interest for these PMMA NPs@sulfonates systems as a promising formulation for theranostic applications. In vivo biological data strongly support the potential value of these core-shell NPs as delivery system for negatively charged drugs or biologically active molecules. Additionally, we have demonstrated the ability of these PMMA core-shell nanoparticles to act as efficient carriers of fluorophores. In principle, thanks to the high PMMA NPs external charge density, sequential and very easy post-loading of different sulfonates is achievable, thus allowing the preparation of nanocarriers either with bi-modal drug delivery behaviour or as theranostic systems. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.023

文献信息

• 寡聚苯撑乙烯化合物及其制备方法和应用
  申请人：中国科学院化学研究所

  公开号：CN107382786B

  公开（公告）日：2019-07-12

  本发明涉及抗肿瘤药物领域，公开了一种寡聚苯撑乙烯化合物及其制备方法和应用。本发明提供的寡聚苯撑乙烯化合物具有如式(3)所示的结构，其中，n为2‑10的整数。本发明提供的结构如式(3)所示的化合物具有良好的抑制肿瘤细胞增殖的作用，特别是对耐药肿瘤细胞的增殖也具有良好的抑制作用，但对正常细胞的毒副作用较小。
• Cross-Linking of Thiolated Paclitaxel-Oligo(<i>p</i> -phenylene vinylene) Conjugates Aggregates inside Tumor Cells Leads to “Chemical Locks” That Increase Drug Efficacy
  作者：Lingyun Zhou、Fengting Lv、Libing Liu、Guizhi Shen、Xuehai Yan、Guillermo C. Bazan、Shu Wang

  DOI：10.1002/adma.201704888

  日期：2018.3

  Cross‐linking of the aggregates via oxidation of thiol groups is favored in tumor cells because of the higher reactive oxygen species (ROS) concentration. Cross‐linked aggregates “chemically lock” the multichromophore particle for a more persistent effect. The IC50 of OPV‐S‐PTX for tumor cell line A549 is reduced down to 0.33 × 10−9m from that observed for PTX itself (41 × 10−9m). Enhanced efficacy by OPV‐S‐PTX

  如何降低某些肿瘤细胞对紫杉醇（PTX）和相关紫杉类抗癌药物的耐药性是提高治愈率的主要挑战。因此，设计了具有巯基的寡聚（对-亚苯基亚乙烯基）单元和增强药物功效并逆转耐药性的PTX（OPV-S-PTX）单元。该机制涉及OPV-S-PTX扩散到细胞中，其中π-π相互作用导致聚集。由于较高的活性氧（ROS）浓度，在肿瘤细胞中聚集体通过硫醇基团的氧化交联是有利的。交联的聚集体可“化学锁定”多发色团颗粒，从而产生更持久的效果。肿瘤细胞系A549的OPV‐S‐PTX的IC 50降低至0.33×10 -9 m与PTX本身的观测值相比（41×10 -9 m）。建议通过加速微管束的形成来提高OPV‐S‐PTX的功效。A549 / T接种的异种移植小鼠实验显示，OPV-S-PTX处理可抑制肿瘤生长。总而言之，这些结果表明，OPV-S-PTX通过ROS的内部交联提供了一种区分肿瘤细胞与健康细胞的方法，化学锁定颗粒
• 一种聚合物纳米药物及其制备方法
  申请人：清华大学

  公开号：CN114159577A

  公开（公告）日：2022-03-11

  本发明属于聚合物纳米材料制备技术领域，具体涉及一种聚合物纳米药物及其制备方法。本发明以多种抗癌药物或药物衍生化分子作为油相或者水相单体，通过乳液界面聚合制备聚合物纳米药物。在正常生理环境下，该聚合物纳米药物可以保持结构稳定，对正常细胞低毒；在肿瘤酸性微环境中，该聚合物纳米药物可以水解释放抗癌药物，发挥其抗癌作用。基于乳液界面聚合法制备的聚合物纳米药物具有载药率高、稳定性好、不需要外加载体、粒径可控和制备方法简便易操作等优点。
• Synthesis of Water-Soluble Paclitaxel Derivatives by Enzymatic Acylation
  作者：Yuri L. Khmelnitsky、Cheryl Budde、J. Michael Arnold、Alexander Usyatinsky、Douglas S. Clark、Jonathan S. Dordick

  DOI：10.1021/ja973103z

  日期：1997.11.1
• US8278264B2
  申请人：——

  公开号：US8278264B2

  公开（公告）日：2012-10-02