palladium 3¹-(3-sulfopropylimino)bacteriochlorin 13¹,17³-di(3-sulfopropyl)amide tripotassium salt

• 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: palladium 3¹-(3-sulfopropylimino)bacteriochlorin 13¹,17³-di(3-sulfopropyl)amide tripotassium salt
• 英文别名: potassium;3-[3-[(2S,3S,12R,13R)-13-ethyl-20-(2-methoxy-2-oxoethyl)-3,7,12,17-tetramethyl-8-[C-methyl-N-(3-sulfonatopropyl)carbonimidoyl]-18-(3-sulfonatopropylcarbamoyl)-2,3,12,13-tetrahydroporphyrin-22,24-diid-2-yl]propanoylamino]propane-1-sulfonate;palladium(2+)
• 化学式: C₄₄H₅₆N₇O₁₃S₃*3K*Pd
• 分子量: 1210.88
• InChiKey: QRNUFVBLAOWCBK-MKCKBKFTSA-I

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  69
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  320
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  3-氨基丙烷磺酸 、 palladium bacteriopheophorbide a 17³-(3-sulfopropyl)amide potassium salt 以 phosphate buffer 、 二甲基亚砜 为溶剂， 以81%的产率得到palladium 3-oxo-15-methoxycarbomylmethyl-rhodobacteriochlorin 13,17-di-(3-sulfopropyl)amide dipotassium salt
  参考文献：
  名称：

  Novel Water-soluble Bacteriochlorophyll Derivatives for Vascular-targeted Photodynamic Therapy: Synthesis, Solubility, Phototoxicity and the Effect of Serum Proteins¶

  摘要：

  New negatively charged water-soluble bacteriochlorophyll (Bch1) derivatives were developed in our laboratory for vascular-targeted photodynamic therapy (VTP). Here we focused on the synthesis, characterization and interaction of the new candidates with serum proteins and particularly on the effect of serum albumin on the photocytotoxicity of WST11, a representative compound of the new derivatives. Using several approaches, we found that aminolysis of the isocyclic ring with negatively charged residues markedly increases the hydrophilicity of the Bch1 sensitizers, decreases their self-association constant and selectively increases their affinity to serum albumin, compared with other serum proteins. The photocytotoxicity of the new candidates in endothelial cell culture largely depends on the concentration of the serum albumin. Importantly, after incubation with physiological concentrations of serum albumin (500-600 mu M), WST11 was found to be poorly photocytotoxic (> 80% endothelial cell survival in cell cultures). However, in a recent publication (Mazor, O. et aL [2005] Photochem. Photobiol. 81,342-351) we showed that VTP of M2R melanoma xenografts with a similar WST11 concentration resulted in similar to 100% tumor flattening and > 70% cure rate. We therefore propose that the two studies collectively suggest that the antitumor activity of WST11 and probably of other similar candidates does not depend on direct photointoxication of individual endothelial cells but on the vascular tissue response to the VTP insult.

  DOI：

  10.1562/2004-12-01-ra-389r1.1