hematoporphyrin IX dihydrochloride | 17696-69-4

• 物质功能分类: 原料药 - 神经系统用药 - 抗抑郁、躁狂药
• 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: hematoporphyrin IX dihydrochloride
• 英文别名: haematoporphyrin dihydrochloride；hematoporphyrin dihydrochioride；hematoporphyrin dihydrochloride；hematoporphyrin; dihydrochloride；Haematoporphyrin; Dihydrochlorid
• CAS: 17696-69-4
• 化学式: C₃₄H₃₈N₄O₆*2ClH
• 分子量: 671.621
• InChiKey: MGHOGMAFXGLVGW-IDTMDVKXSA-N

物化性质

• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  45.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  172.42
• 氢给体数：
  6.0
• 氢受体数：
  6.0

安全信息

• TSCA：
  Yes
• 危险类别码：
  R33
• RTECS号：
  TS5505000

制备方法与用途

应用

有研究表明血卟啉二盐酸盐可用于制备具有高结晶速率的树脂组合物，其包含聚呋喃二甲酸亚烷基酯(polyalkylenefurandicarboxylate)树脂和卟啉化合物。该聚呋喃二甲酸亚烷基酯树脂优选为聚呋喃二甲酸亚丁基酯树脂。该卟啉化合物优选为血卟啉二盐酸盐(hematoporphyrindihydrochloride)。

生物活性

Hematoporphyrin dihydrochloride (Hematoporphyrin IX dihydrochloride) 是一种光敏剂，是血红素结合蛋白亲和色谱底物。当暴露于红光下时，Hematoporphyrin dihydrochloride 可以诱导 U87 胶质瘤细胞凋亡，并降低体内肿瘤的生长。

体外研究

Hematoporphyrin (20-120 nM; 60 min) dose-dependently inhibits cell viability in U87 and U251 glioma cells, with IC ₅₀ s of 85 and 166 nM, respectively.
Hematoporphyrin (85 nM; 60 min) induces cell apoptosis via induction of ROS in U87 cells.
Hematoporphyrin (85 nM; 60 min) induces morphological changes of U87 cells under the red light, including shrinking, fragmentation.

Cell Viability Assay

Cell Line:	U87 and U251 cells
Concentration:	20, 40, 60, 80, 100, 120 nM
Incubation Time:	60 min
Result:	Inhibited cell viability in a dose-dependent manner. Was more effective under the red light than white light.

Apoptosis Analysis

Cell Line:	U87 cells
Concentration:	85 nM
Incubation Time:	60 min
Result:	Induced apoptotic nuclei in U87 cells with low cell density. Induced the ROS and decreased the mitochondrial membrane potential.

体内研究

Hematoporphyrin (5-10 mg/kg; i.p. for 2 months) with the irradiation of red light rapidly decreases the tumor size of rats, due to necrosis caused both by direct action of the photoactivated porphyrin on the tumor cells and by secondary effects on blood vessels.

Animal Model:	Wistar albino rats of both sexes (20 d; 60-80 g) bearing a subcutaneous solid Yoshida hepatoma AH-130
Dosage:	5, 10 mg/kg
Administration:	I.p. daily during the initial 10 days and biweekly for the next 2 months
Result:	No tumor could be palpated a few days after exposure of the rats to light. The skin healed completely and regrowth of the hair occurred. Massive coagulation necrosis of the tumor 24 h after phototreatment (×40).

反应信息

• 作为反应物：
  描述：

  hematoporphyrin IX dihydrochloride 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-(1-acetoxyethyl)-8-vinyldeuteroporphyrin
  参考文献：
  名称：

  关于“血卟啉衍生物”的性质

  摘要：

  血卟啉衍生物（一种在临床应用中用作光敏剂的制剂，通过用硫酸-乙酸处理血卟啉制得）的成分已通过制备型hplc进行了分离，并与真卟啉二羧酸进行了比较。该混合物的组合物是一些-什么可变的，但主要成分是ö，Ö '-diacetylhaematoporphyrin（6）和Ô -acetylhaematoporphyrin（2）/（3）与较少量的8（3）的- （1-乙酰氧基乙基） -3（8）-乙烯基氘化卟啉异构体（7）和（8）以及相应的醇（4）和（5）。

  DOI：

  10.1039/p19810003135

文献信息

• Haematoporphyrin derivative
  作者：Raymond Bonnett、Richard J. Ridge、Panayiotis A. Scourides、Morris C. Berenbaum

  DOI：10.1039/c39800001198

  日期：——

  Components of ‘haematoporphyrin derivative,’ a photosensitiser employed in clinical studies, have been separated as the free acids by reverse-phase high pressure liquid chromatography, and identified, the major components being O,O′-diacetylhaematoporphyrin and O-acetylhaematoporphyrin.

  “血卟啉衍生物，”在临床研究中使用的光敏剂，的部件已被分离出作为游离酸通过反相高压液相色谱，和识别时，主要成分为ø，ö '-diacetylhaematoporphyrin和Ò -acetylhaematoporphyrin。
• An improved synthesis of porphyrin C
  作者：Panayiotis A. Scourides、George Morstyn、Maria Ngu

  DOI：10.1039/c39860001817

  日期：——

  A synthesis of porphyrin c from haematoporphyrin in high yield and purity is described.

  描述了由血卟啉以高产率和高纯度合成卟啉c。
• Radio labeled dihematoporphyrin ether and its use in detecting and treating neoplastic tissue
  申请人：UNIVERSITY OF CINCINNATI

  公开号：EP0190905A2

  公开（公告）日：1986-08-13

  Radiolabeled dihematopophyrin ether having the following general formula wherein at least one of R1-R6 is a moiety labeled with a radionuclide imaging agent is useful in providing a non--invasive nuclear scintillation image. This dihematoporphyrin ether localizes in neoplastic tissue and thus provides a method of imaging and recording the location of neoplastic tissue. When the labeling agent has an adequate component of particulate radiation, the dihematoporphyrin ether can be used as a therapeutic agent as well as a diagnostic imaging agent

  具有以下通式的放射性标记二氢叶绿素醚 其中 R1-R6 至少有一个是用放射性核素成像剂标记的分子，可用于提供非侵入性核闪烁图像。这种二氢卟啉醚可定位在肿瘤组织中，因此提供了一种成像和记录肿瘤组织位置的方法。当标记剂中含有足够的微粒辐射成分时，二hematorphyrin 醚既可用作治疗剂，也可用作诊断成像剂。
• Photodynamic therapy using chemoluminescence and a ligand-photosensitiser conjugate
  申请人：Ariel-University Research And Development Company

  公开号：EP2308508A1

  公开（公告）日：2011-04-13

  The present invention concers a ligand-toxin conjugate (LTC) comprising a photosensitizer (Ps) and a ligand linked thereto, for use in combination with a chemiluminiscent agent which reacts with an oxygen species present in situ and produces chemiluminescent light, wherein said Ps transfers energy to molecular oxygen and produces reactive oxygen species when light-activated by said chemiluminescent agent, in the treatment of a disorder associated with undesired activity of a cell population.

  本发明包含一种配体-毒素共轭物（LTC），该共轭物由光敏剂（Ps）和与之相连的配体组成，可与化学发光剂结合使用，化学发光剂可与原位存在的氧物种发生反应并产生化学发光，其中所述 Ps 可将能量转移到分子氧上，并在所述化学发光剂的光激活下产生活性氧物种，用于治疗与细胞群的不良活性有关的紊乱。
• PHOTOSENSITZER CONJUGATES FOR TARGETING INTRACELLULAR PATHOGENS
  申请人：——

  公开号：US20020122805A1

  公开（公告）日：2002-09-05

  The methods of the invention can be used to treat mycobacterial infections, or any disease or disorder that is caused by (or aggravated by) an intracellular pathogen. Accordingly, the invention features methods for treating a subject who has a disorder that is associated with an intracellular pathogen by administering, to a subject, a molecular conjugate that includes a photosensitizer (a term used herein to refer to a light activatable compound) and a targeting moiety, the targeting moiety being capable of targeting the conjugate to the intracellular pathogen.

  本发明的方法可用于治疗分枝杆菌感染或任何由细胞内病原体引起（或加重）的疾病或紊乱。因此，本发明的特点是通过向受试者施用分子共轭物来治疗与细胞内病原体有关的疾病，该分子共轭物包括光敏剂（此处的术语是指可被光激活的化合物）和靶向分子，靶向分子能够将共轭物靶向细胞内病原体。