3-oxo-15¹-methoxycarbonylmethyl-rhodobacteriochlorin 13¹-(2-sulfethyl)amide palladium

• 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: 3-oxo-15¹-methoxycarbonylmethyl-rhodobacteriochlorin 13¹-(2-sulfethyl)amide palladium
• 英文别名: WST11；3-[(2S,3S,12R,13R)-8-acetyl-13-ethyl-20-(2-methoxy-2-oxoethyl)-3,7,12,17-tetramethyl-18-(2-sulfonatoethylcarbamoyl)-2,3,12,13-tetrahydroporphyrin-22,24-diid-2-yl]propanoate;hydron;palladium(2+)
• 化学式: C₃₇H₄₃N₅O₉PdS
• 分子量: 840.263
• InChiKey: MZRDSGWDVDESRC-VNWQTDIGSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  199
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  牛磺酸 、 palladium-bacteriopheophorbide 在 盐酸 、 dipotassium hydrogenphosphate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 3-oxo-15¹-methoxycarbonylmethyl-rhodobacteriochlorin 13¹-(2-sulfethyl)amide palladium
  参考文献：
  名称：

  [EN] SYNTHESIS AND COMPOSITION OF PHOTODYNAMIC THERAPEUTIC AGENTS FOR THE TARGETED TREATMENT OF CANCER
  [FR] SYNTHÈSE ET COMPOSITION D'AGENTS THÉRAPEUTIQUES PHOTODYNAMIQUES POUR LE TRAITEMENT CIBLÉ DU CANCER

  摘要：

  本发明描述了一种新的化合物，可用于图像引导手术和光动力疗法。特别是，化合物可以通过使用针对表达在患病组织上的受体的配体将化合物输送到疾病组织（如癌症），然后通过受体介导的内吞作用定位到细胞核或线粒体，并对癌细胞以及其他疾病提供有效的活性。同时还描述了使用该化合物的方法和组合物。

  公开号：

  WO2017044443A1

文献信息

• [EN] SYNTHESIS AND COMPOSITION OF PHOTODYNAMIC THERAPEUTIC AGENTS FOR THE TARGETED TREATMENT OF CANCER<br/>[FR] SYNTHÈSE ET COMPOSITION D'AGENTS THÉRAPEUTIQUES PHOTODYNAMIQUES POUR LE TRAITEMENT CIBLÉ DU CANCER
  申请人：ON TARGET LABORATORIES LLC

  公开号：WO2017044443A1

  公开（公告）日：2017-03-16

  The present invention describes new compounds that are useful for image-guided surgery and photodynamic therapy. In particular the compounds may be targeted to the nucleus or the mitochondria after compounds were delivered to diseased tissues such as cancer using a ligand that target receptor that express on the diseased tissue and followed by receptor mediated endocytosis and provide effective activity against cancer cells as well as other disorders. Methods and compositions for use of the same are described.

  本发明描述了一种新的化合物，可用于图像引导手术和光动力疗法。特别是，化合物可以通过使用针对表达在患病组织上的受体的配体将化合物输送到疾病组织（如癌症），然后通过受体介导的内吞作用定位到细胞核或线粒体，并对癌细胞以及其他疾病提供有效的活性。同时还描述了使用该化合物的方法和组合物。
• Modulation of Reactive Oxygen Species Photogeneration of Bacteriopheophorbide <i>a</i> Derivatives by Exocyclic E-Ring Opening and Charge Modifications
  作者：Áron Roxin、Juan Chen、Andrew S. Paton、Timothy P. Bender、Gang Zheng

  DOI：10.1021/jm401538h

  日期：2014.1.9

  With the knowledge that the dominant photodynamic therapy (PDT) mechanism of la (WST09) switched from type 2 to type 1 for 1b (WST11) upon taurine-driven E-ring opening, we hypothesized that taurine-driven E-ring opening of bacteriochlorophyll derivatives and net-charge variations would modulate reactive oxygen species (ROS) photogeneration. Eight bacteriochlorophyll a derivatives were synthesized with varying charges that either contained the E ring (2a-5a) or were synthesized by taurine-driven E-ring opening (2b-513). Time-dependent density functional theory (TDDFT) modeling showed that all derivatives would be type 2 PDT-active, and ROS-activated fluorescent probes were used to investigate the photogeneration of a combination of type 1 and type 2 PDT ROS in organic- and aqueous-based solutions. These investigations validated our predictive modeling calculations and showed that taurine-driven E-ring opening and increasing negative charge generally enhanced ROS photogeneration in aqueous solutions. We propose that these structure activity relationships may provide simple strategies for designing bacteriochlorins that efficiently generate ROS upon photoirradiation.