| 916428-87-0

• CAS: 916428-87-0
• 化学式: C₄₄H₄₂N₁₂O₂Si
• 分子量: 798.982
• InChiKey: PWZXBZIVMDZGOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  DBCO-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， 反应 24.0h， 以54%的产率得到
  参考文献：
  名称：

  Photodynamic therapy via FRET following bioorthogonal click reaction in cancer cells

  摘要：

  Longer wavelength light (650-800 nm) is desired to treat large tumors in photodynamic therapy (PDT). However, shorter wavelength light is needed in PDT for thin tumors, not to cause undesirable local side effects. We proposed a strategy for stepwise optical imaging and PDT using a bioorthogonal click chemistry and fluorescence resonance energy transfer (FRET). We prepared azidyl rhodamine (Rh-N-3, clickable FD) and cyclooctynyl phthalocyanine [Pc-(DIBAC), clickable PS], with which, here, we demonstrate that the non-catalytic click chemistry is rapid and efficient in cancer cells and FRET from a fluorescence dye (FD) to a photosensitizer (PS) is sufficient to generate enough singlet oxygen killing cancer cells by using shorter wavelength light. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.014
• 作为产物：
  描述：

  N-羟乙基哌嗪 、 酞菁二氯化硅 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以42%的产率得到
  参考文献：
  名称：

  用于肿瘤光动力治疗的强肽共轭硅酞菁。

  摘要：

  酞菁（Pcs）是一组用于光动力疗法（PDT）的有前途的光敏剂。但是，它们的极低溶解度和在水溶液中聚集的强烈趋势极大地限制了它们的应用。Pc大环与肽配体的缀合可能是一种非常有用的策略，不仅可以通过增加Pc的水溶性和降低其聚集度，而且还可以通过赋予缀合物以肿瘤靶向能力来优化Pc的物理性质。为了开发用于肿瘤PDT的高效光敏剂，我们使用硅Pc（SiPc）作为光激活部分和cRGDfK肽（或简称cRGD）作为肽，使用具有比锌Pcs高得多的光动力活性的硅Pc（SiPc）制备了新的肽偶联光敏剂。部分。还测试了聚乙二醇接头和额外的羧酸基团以引入缀合物中以优化缀合物结构。然后使用体外和体内实验仔细评估并比较缀合物的光物理和光动力学行为。制备的偶联物之一RGD-（Linker）2-Glu-SiPc显示出优异的物理性能和光动力活性，对多种癌细胞的EC50（半数最大有效浓度）为10-20 nM。仅需一剂光动力治疗，

  DOI：

  10.7150/jca.22362

文献信息

• 具有双摄取通路的轴向磺酸基修饰酞菁硅及其制备方法及和应用
  申请人：福州大学

  公开号：CN114805372A

  公开（公告）日：2022-07-29

  本发明公开了一种具有双摄取通路的轴向磺酸基修饰酞菁硅及其制备方法和应用。本发明设计的酞菁硅可以通过磺酸阴离子和白蛋白介导的双摄取途径被HepG2细胞吸收，产生极高的光细胞毒性，IC50值为2.0 nM。另外，本发明所述的磺酸基修饰酞菁与白蛋白复合物不仅提高了酞菁的光活性（如荧光发射和活性氧的产生），而且能在血液中的FBS的存在下完全解聚，产生最大的光敏活性。磺酸基修饰酞菁与白蛋白复合物的肿瘤靶向性也显著增强，能够实现有效的体内荧光成像和光动力治疗。这是首个阴离子酞菁通过有机阴离子转运多肽（OATP）途径摄取的例子，也是光敏剂通过分子和超分子介导的双重细胞摄取途径的首个例子。
• Folate Receptor-Mediated Enhanced and Specific Delivery of Far-Red Light-Activatable Prodrugs of Combretastatin A-4 to FR-Positive Tumor
  作者：Gregory Nkepang、Moses Bio、Pallavi Rajaputra、Samuel G. Awuah、Youngjae You

  DOI：10.1021/bc500376j

  日期：2014.12.17

  We examined the concept of a novel prodrug strategy in which anticancer drug can be locally released by visible/near IR light, taking advantage of the photodynamic process and photo-unclick chemistry. Our most recently formulated prodrug of combretastatin A-4, Pc-(L-CA4)2, showed multifunctionality for fluorescence imaging, light-activated drug release, and the combined effects of PDT and local chemotherapy. In this formulation, L is a singlet oxygen cleavable linker. Here, we advanced this multifunctional prodrug by adding a tumor-targeting group, folic acid (FA). We designed and prepared four FA-conjugated prodrugs 1-4 (CA4-L-Pc-PEGn-FA: n = 0, 2, 18, ∼45) and one non-FA-conjugated prodrug 5 (CA4-L-Pc-PEG18-boc). Prodrugs 3 and 4 had a longer PEG spacer and showed higher hydrophilicity, enhanced uptake to colon 26 cells via FR-mediated mechanisms, and more specific localization to SC colon 26 tumors in Balb/c mice than prodrugs 1 and 2. Prodrug 4 also showed higher and more specific uptake to tumors, resulting in selective tumor damage and more effective antitumor efficacy than non-FA-conjugated prodrug 5. FR-mediated targeting seemed to be an effective strategy to spare normal tissues surrounding tumors in the illuminated area during treatment with this prodrug.
• Far-Red Light Activatable, Multifunctional Prodrug for Fluorescence Optical Imaging and Combinational Treatment
  作者：Moses Bio、Pallavi Rajaputra、Gregory Nkepang、Youngjae You

  DOI：10.1021/jm5000722

  日期：2014.4.24

  We recently developed "photo-unclick chemistry", a novel chemical tool involving the cleavage of aminoacrylate by singlet oxygen, and demonstrated its application to visible light-activatable prodrugs. In this study, we prepared an advanced multifunctional prodrug, Pc-(L-CA4)(2), composed of the fluorescent photosensitizer phthalocyanine (Pc), an SO-labile aminoacrylate linker (L), and a cytotoxic drug combretastatin A-4 (CA4). Pc-(L-CA4)(2) had reduced dark toxicity compared with CA4. However, once illuminated, it showed improved toxicity similar to CA4 and displayed bystander effects in vitro. We monitored the time-dependent distribution of Pc-(L-CA4)(2) using optical imaging with live mice. We also effectively ablated tumors by the illumination with far-red light to the mice, presumably through the combined effects of photodynamic therapy (PDT) and released chemotherapy drug, without any sign of acute systemic toxicity.
• Far-Red Light-Activatable Prodrug of Paclitaxel for the Combined Effects of Photodynamic Therapy and Site-Specific Paclitaxel Chemotherapy
  作者：Pritam Thapa、Mengjie Li、Moses Bio、Pallavi Rajaputra、Gregory Nkepang、Yajing Sun、Sukyung Woo、Youngjae You

  DOI：10.1021/acs.jmedchem.5b01971

  日期：2016.4.14

  Paclitaxel (PTX) is one of the most useful chemotherapeutic agents approved for several cancers, including ovarian, breast, pancreatic, and nonsmall cell lung cancer. However, it causes systemic side effects when administered parenterally. Photodynamic therapy (PDT) is a new strategy for treating local cancers using light and photosensitizer. Unfortunately, PDT is often followed by recurrence due to incomplete ablation of tumors. To overcome these problems, we prepared the far-red light-activatable prodrug of PTX by conjugating photosensitizer-via singlet oxygen-cleavable aminoacrylate linker. Tubulin polymerization enhancement and cytotoxicity of prodrugs were dramatically reduced. However, once illuminated with far-red light, the prodrug effectively killed SKOV-3 ovarian cancer cells through the combined effects of PDT and locally released PTX. Ours is the first PTX prodrug that can be activated by singlet oxygen using tissue penetrable and clinically useful far-red light, which kills the cancer cells through the combined effects of PDT and site specific PTX chemotherapy.