dimethyl 3,3′-(7,12-bis(1-bromoethyl)-3,8,13,17-tetramethylporphyrin-2,18-diyl)dipropionate | 110084-83-8

• 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: dimethyl 3,3′-(7,12-bis(1-bromoethyl)-3,8,13,17-tetramethylporphyrin-2,18-diyl)dipropionate
• 英文别名: bis(α-methyl-β-bromo)protoporphyrin IX dimethyl ester
• CAS: 110084-83-8
• 化学式: C₃₆H₄₀Br₂N₄O₄
• 分子量: 752.546
• InChiKey: GPCINEGTJQGQJS-HRBATZQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.09
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  109.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl 3,3′-(7,12-bis(1-bromoethyl)-3,8,13,17-tetramethylporphyrin-2,18-diyl)dipropionate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 123.0h， 生成 7,12-bis[1-(1,4,7,10-tetraoxaundecyl)ethyl]-3,8,13,17-tetramethylporphyrin-2,18-dipropionic acid
  参考文献：
  名称：

  Hematoporphyrin-Derived Soluble Porphyrin−Platinum Conjugates with Combined Cytotoxic and Phototoxic Antitumor Activity

  摘要：

  To combine the cytotoxic activity of cisplatin and the phototoxicicity of hematoporphyrin derivatives in the same molecule, hematoporphyrin was derivatized at the two secondary alcohol positions by etherification with oligo- and poly(ethylene glycol) units. The two carboxylic acid groups of the propionate side chains were used to bind platinum fragments, The antiproliferative activity of 35 platinum complexes (0.5, 1, and 5 muM) differing in solubility and type of the platinum fragment and the corresponding porphyrin ligands were studied in tests with TCC-SUP and J82 transitional bladder cancer cells in the dark and after irradiation (lambda = 600-730 nm, 24 J/cm(2)). The most active compounds were found among the porphyrin-platinum conjugates bearing the diammine and (RR/SS)-trans-1,2-diaminocyclohexane ligand. These porphyrin-platinum conjugates, especially the water-soluble species, such as diammine{7,12-bis[1-(poly(ethylene glycol)-750-monomethyl ether-1-yl)ethyl]-3,8,13,17-tetramethylporphyrin-2,18-dipropionato}platinum(II), are promising candidates for the development of a novel type of photosensitizers with intrinsic cytotoxicity, which due to the porphyrin constituent may selectively enrich in tumor tissues.

  DOI：

  10.1021/jm0110688
• 作为产物：
  描述：

  protoporphyrin IX 在 硫酸 、 氢溴酸 、 溶剂黄146 作用下， 反应 20.0h， 生成 dimethyl 3,3′-(7,12-bis(1-bromoethyl)-3,8,13,17-tetramethylporphyrin-2,18-diyl)dipropionate
  参考文献：
  名称：

  Synthesis of protoporphyrin–lipids and biological evaluation of micelles and liposomes

  摘要：

  Protoporphyrin IX (PPIX) lipids were synthesized by introducing a long alkyl chain, such as C13, C15, and C17, at each vinyl group on PPIX via hydrobromination. The PPIX lipids exhibited a water-soluble property by forming their micelles in water and the PPIX-lipid micelles showed relatively low cytotoxicity toward HeLa cells (IC50=151.7-379.9μM) without light irradiation. PL-C17 liposomes (post-inserted liposomes) were readily prepared by adding PL-C17 micelle solution to the liposome solution. The IC50 values of PPIX, PL-C17 micelles, and PL-C17 liposomes toward HeLa cells were 0.53, 5.65, and 12.9μM, respectively, after irradiation with a xenon lamp in the 400-800nm range for 2min. PL-C17 liposomes were selectively accumulated in the Golgi apparatus in cells.

  DOI：

  10.1016/j.bmc.2014.07.003

文献信息

• Boron-Containing Protoporphyrin IX Derivatives and Their Modification for Boron Neutron Capture Therapy: Synthesis, Characterization, and Comparative In Vitro Toxicity Evaluation
  作者：Mohamed E. El-Zaria、Hyun Seung Ban、Hiroyuki Nakamura

  DOI：10.1002/chem.200901532

  日期：2010.2.1

  use in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) for tumor suppression is described. Protoporphyrin IX i.e., bis(α‐methyl‐β‐pentylethylether)protoporphyrin IX, and bis(α‐methyl‐β‐dodecanylethylether)protoporphyrin IX} bearing polyhedral borane anions (B12H11SH2−, B12H11NH3−, or B12H11OH2−) were synthesized with reasonable yields. Modification of the protoporphyrin IX structure

  描述了一系列潜在用于硼中子俘获疗法（BNCT）和光动力疗法（PDT）抑制肿瘤的新型硼化卟啉。带有多面硼烷阴离子（B 12 H 11 SH 2−，B 12 H 11 NH的原卟啉IX 即，双（α-甲基-β-戊基乙基醚）原卟啉IX和双（α-甲基-β-十二烷基乙基醚）原卟啉IX} 3 - ，或B 12 ħ 11 OH 2-）以合理的产率合成。通过改变通过醚键连接到前一个乙烯基上的烷基链（戊基和十二烷基）的长度，可以实现原卟啉IX结构的修饰。该修饰的目的是开发具有不同于原卟啉IX的化学和物理性质的硼化卟啉。用每种衍生物进行MTT分析表明，合成的硼化卟啉在多种癌细胞中显示出低细胞毒性。在这些化合物中，B 12 H 11 NH 2 2-共轭卟啉可显着提高硼积累水平和PDT对HeLa细胞的功效。
• 含ホウ素ポルフィリン誘導体
  申请人：学校法人 学習院

  公开号：JP2015071625A

  公开（公告）日：2015-04-16

  【課題】光線力学療法やホウ素中性子捕捉療法に有用な、腫瘍細胞親和性に優れ、かつ、毒性が低い、含ホウ素ポルフィリン誘導体の提供。【解決手段】式（１）で表されるアニオン化合物の塩である含ホウ素ポルフィリン誘導体。［Ｒ１及びＲ２は各々独立に置換／未置換のアルキル基又はビニル基；Ｒ３はＸＢ１２Ｈ１１２−（ＸはＯ，Ｓ又はＮＨ）又はＮＨ２Ｂ１２Ｈ１１−；Ｒ４は水酸基、ＸＢ１２Ｈ１１２−（Ｘは前記と同義）又はＮＨ２Ｂ１２Ｈ１１−］【選択図】図１

  【课题】提供一种含硼卟啉衍生物，它具有优异的肿瘤细胞亲和性和低毒性，可用于光子力学疗法和硼中子俘获疗法。【解决方法】所述含硼卟啉衍生物是由式（1）表示的阴离子化合物的盐制备而成。[R1和R2各自独立地是取代/未取代的烷基或乙烯基；R3是XB112H112-（X是O、S或NH）或NH2B112H11-；R4是羟基、XB112H112-（X与前面相同）或NH2B112H11-] 【选图】图1
• Regioselective syntheses of ether-linked porphyrin dimers and trimers related to photofrin-II®
  作者：Ravindra K. Pandey、Fuu-Yau Shiau、Thomas J. Dougherty、Kevin M. Smiths

  DOI：10.1016/s0040-4020(01)91025-7

  日期：1991.11

  Using isomerically pure 4-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 10, 2-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 11, 2-acetyl-4-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 12 and 4-acetyl-2-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 13 as starting materials, a series of regiochemically pure ether-linked porphyrin dimers 25–41 and trimers 42–47 related to an anticancer

  使用异构体纯的4-（1-羟乙基）次卟-IX二甲酯10，2-（1-羟乙基）次卟-IX二甲酯11 2-乙酰基-4-（1-羟乙基）次卟-IX二甲酯12和4 -乙酰基-2-（1-羟乙基）氘卟啉-IX二甲酯13作为起始原料，一系列区域化学纯的醚连接卟啉二聚体25-41和三聚体42-47合成了与一种称为Photofrin-II®的抗癌药物有关的药物。质子NMR核Overhauser增强实验和可变温度质子NMR光谱用于表征异构体。测试了其中某些化合物相对于Photofrin-II的体内光敏能力，并简要描述了初步结果。
• JP5747267
  申请人：——

  公开号：——

  公开（公告）日：——
• Syntheses, stability, and tumorcidal activity of porphyrin dimers and trimers with ether linkages
  作者：Ravindra K. Pandey、Fuu-Yau Shiau、Craig J. Medforth、Thomas J. Dougherty、Kevin M. Smith

  DOI：10.1016/s0040-4039(00)88499-3

  日期：1990.1

  The first syntheses of a series of regiochemically pure porphyrin dimers and trimers with ether linkages which are structurally related to Photofrin-II(R) are described. Stability of these oligomers was investigated using variable temperature proton NMR spectroscopy, and preliminary biological results reveal that manupulation of peripheral substituents causes a remarkable difference in photosensitizing ability in vivo.