meso-tetrakis<4-(2-hydroxyethoxy)phenyl>porphyrin | 64395-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: meso-tetrakis<4-(2-hydroxyethoxy)phenyl>porphyrin
• 英文别名: 2H-5,10,15,20-tetrakis[4-(2-hydroxyethoxy)phenyl]porphyrin；Tetra-meso-porphyrin；2,2',2'',2'''-(4,4',4'',4'''-porphyrin-5,10,15,20-tetrayl-tetraphenoxy)-tetrakis-ethanol
• CAS: 64395-04-6
• 化学式: C₅₂H₄₆N₄O₈
• 分子量: 854.959
• InChiKey: BQLHKVZEPBPQOJ-RCOMQYLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.81
• 重原子数：
  64.0
• 可旋转键数：
  16.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  175.2
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  4-(2-羟基乙氧基)苯甲醛 在 三氟化硼乙醚 、 原乙酸三乙酯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 meso-tetrakis<4-(2-hydroxyethoxy)phenyl>porphyrin
  参考文献：
  名称：

  Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions

  摘要：

  DOI：

  10.1021/jo00381a022

文献信息

• Hydroxyalkyloxy substituted tetraphenylporphyrins: Mechanism and superoxide scavenging activity
  作者：Sergey M. Kuzmin、Svetlana A. Chulovskaya、Vladimir I. Parfenyuk

  DOI：10.1142/s1088424616501212

  日期：2016.12

  The novel electrochemical approach based on coulometric response of electro-generated superoxide (O[Formula: see text] was used to determine scavenging properties of 2H-5,10,15,20-tetrakis (4-hydroxyphenyl)porphyrin (H[Formula: see text]T(4-OHPh)P); 2H-5,10,15,20-tetrakis[4-(2-hydroxyethyloxy)phenyl]porphyrin (H[Formula: see text]T(4-OH(CH[Formula: see text]OPh)P); 2H-5,10,15,20-tetrakis[4-(4-hydroxybutyloxy)phenyl]porphyrin (H[Formula: see text]T(4-OH(CH[Formula: see text]OPh)P); Zn-5,10,15,20-tetrakis[4-(4-hydroxyethyloxy)phenyl]porphyrin (ZnT(4-OH(CH[Formula: see text]OPh)P) superoxide. It has been identified that the porphyrins under study possess good antioxidant properties. The analysis of possible interactions between porphyrins and superoxide anion-radical has shown that high values of superoxide scavenging activity of tetraphenylporphyrins with alcohol chains can be explained by the nucleophilic attack of O[Formula: see text] on the C–C bonds of alcohol.

  见正文]T(4-OH(CH[式：见正文]OPh)P)；2H-5,10,15,20-四[4-(4-羟基丁酰氧基)苯基]卟啉（H[式：见正文]T(4-OH(CH[式：见正文]OPh)P)P）；Zn-5,10,15,20-四[4-(4-羟乙基氧基)苯基]卟啉（ZnT(4-OH(CH[式：见正文]OPh)P）超氧化物。研究发现，这些卟啉具有良好的抗氧化性。对卟啉和超氧阴离子-自由基之间可能的相互作用进行的分析表明，带有醇链的四苯基卟啉的高超氧清除活性值可以用 O[式：见正文]对醇的 C-C 键的亲核攻击来解释。
• Synthesis, self‐assembly, fluorescence, and thermosensitive properties of star‐shaped amphiphilic copolymers with porphyrin core
  作者：Tianbin Ren、An Wang、Weizhong Yuan、Lan Li、Yue Feng

  DOI：10.1002/pola.24665

  日期：2011.5.15

  Star‐shaped amphiphilic poly(ε‐caprolactone)‐block‐poly(oligo(ethylene glycol) methyl ether methacrylate) with porphyrin core (SPPCL‐b‐POEGMA) was synthesized by combination of ring‐opening polymerization (ROP) and atom transfer radical polymerization (ATRP). Star‐shaped PCL with porphyrin core (SPPCL) was prepared by bulk polymerization of ε‐caprolactone (CL) with tetrahydroxyethyl‐terminated porphyrin

  星形的两亲性聚（ε -己内酯） -嵌段-聚（低聚（乙二醇）甲基醚甲基丙烯酸酯）与卟啉核（SPPCL- b -POEGMA）通过开环聚合（ROP）和原子转移自由基的组合合成聚合（ATRP）。带有卟啉核的星形PCL（SPPCL）是通过ε-己内酯（CL）与四羟乙基封端的卟啉引发剂和2-乙基exanote锡（Sn（Oct）2）催化剂的本体聚合而制备的。将SPPCL与2-溴异丁酰基溴转化为SPPCLBr大分子引发剂。星形SPPCL- b - POEGMA是通过低聚乙二醇乙二醇甲基丙烯酸甲酯（OEGMA）的ATRP获得的。SPPCL‐ b‐POEGMA可以通过透析方法轻松地在水溶液中自组装成胶束。胶束聚集体的形成通过临界胶束形成浓度，动态光散射和透射电子显微镜确认。胶束还表现出温度诱导的药物释放特性，最低临界溶液温度（LCST）为60.6°C。此外，SPPCL- b- POEGMA胶束可响应外部温度而可逆溶胀和收缩。此外，SPPCL‐
• Supramolecular amphiphilic star-branched copolymer: from LCST–UCST transition to temperature–fluorescence responses
  作者：Weizhong Yuan、Hui Zou、Wen Guo、An Wang、Jie Ren

  DOI：10.1039/c2jm35297d

  日期：——

  The novel and well-defined supramolecular amphiphilic star-branched copolymer poly((caprolactone)-star-(poly(2-N,N-dimethylamino)ethylmethacrylate)7 (PCL-(PDMAEMA)7) with a porphyrin core was prepared via the combination of ring-opening polymerization (ROP), atom transfer radical polymerization (ATRP), and supramolecular host–guest inclusion complexation. After reaction of PDMAEMA with excess 1,3-propane sultone, the quaternized star-PCL-(PDMAEMA)7 was obtained. The amphiphilic star-PCL-(PDMAEMA)7 and quaternized star-PCL-(PDMAEMA)7 can self-assemble into spherical nano-micelles by directly dissolving in water. This thermoresponsive micelles solution shows a transition from a lower critical solution temperature (LCST) of star-PCL-(PDMAEMA)7 to an upper critical solution temperature (UCST) of quaternized star-PCL-(PDMAEMA)7, indicating that the LCST–UCST transition of micellar solutions can be accomplished by the transition of PDMAEMA to quaternized PDMAEMA. Due to the presence of porphyrin molecules in the micelles core, the micelle solutions present obvious fluorescence and the fluorescent intensity can be adjusted by altering the temperatures. For the star-PCL-(PDMAEMA)7 micelle solution, the fluorescent intensity decreases with the increase of temperature, while the fluorescent intensity increases with the increase of temperature for the quaternized star-PCL-(PDMAEMA)7 micelle solution, indicating unique temperature–fluorescence responsive behavior.

  通过开环聚合（ROP）、原子转移自由基聚合（ATRP）和超分子主客体包合复配，制备了以卟啉为核心的新型、定义明确的超分子两亲星形支链共聚物聚（（己内酯）-星形-（聚（2-N,N-二甲基氨基）乙基甲基丙烯酸酯）7（PCL-（PDMAEMA）7）。PDMAEMA 与过量的 1,3-丙烷内酯反应后，得到季铵化的星形-PCL-(PDMAEMA)7。两亲性星型-PCL-(PDMAEMA)7 和季铵化星型-PCL-(PDMAEMA)7 可直接溶解在水中自组装成球形纳米胶束。这种热致胶束溶液显示出从星形-PCL-(PDMAEMA)7的下临界溶液温度（LCST）到季铵化星形-PCL-(PDMAEMA)7的上临界溶液温度（UCST）的转变，表明胶束溶液的LCSTâUCST转变可以通过PDMAEMA向季铵化PDMAEMA的转变来实现。由于胶束核心含有卟啉分子，胶束溶液呈现出明显的荧光，荧光强度可通过改变温度来调节。在星形-PCL-（PDMAEMA）7胶束溶液中，荧光强度随温度升高而降低，而在季铵化星形-PCL-（PDMAEMA）7胶束溶液中，荧光强度随温度升高而升高，显示出独特的温度荧光响应行为。
• Glycol Porphyrin Derivatives as Potent Photodynamic Inducers of Apoptosis in Tumor Cells
  作者：Jarmila Králová、Tomáš Bříza、Irena Moserová、Bohumil Dolenský、Petr Vašek、Pavla Poučková、Zdeněk Kejík、Robert Kaplánek、Pavel Martásek、Michal Dvořák、Vladimír Král

  DOI：10.1021/jm8002119

  日期：2008.10.9

  The design and synthesis of glycol-functionalized porphyrins that contain one to four low molecular weight glycol chains that are linked via ether bonds to the meta-phenyl positions of meso-tetraphenylporphyrin and the comparison of fluorinated and nonfluorinated para derivatives are reported. The cellular uptake and photodynamic activity significantly depend on terminal groups of the glycol substituent. Hydroxy glycol porphyrins, in contrast with methoxy glycol porphyrins, show efficient intracellular transport and a high induction of apoptosis in tumor cell lines in vitro. Furthermore, the ethylene glycol chain at the meta position exhibits a superior efficacy that leads to the permanent ablation of human breast carcinoma (MDA-MB-231) in nude mice. In addition, fluorination enhanced the photosensitizing potential of para-phenyl derivatives. The analysis of the cell-death mechanism revealed that glycol-functionalized porphyrins represent novel nonmitochondrially localized photosensitizers that have a profound ability to induce apoptosis in tumor cells that act upstream of caspase activation. The strong interaction with a tumor marker (sialic acid) indicates the preferential association of these compounds with tumor cells.