3¹-oxo-15-methoxycarbonylmethyl-rhodobacteriochlorin-13¹-(2-sulfethyl)amide-17³-(2-trimethylaminoethyl)ester

• 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: 3¹-oxo-15-methoxycarbonylmethyl-rhodobacteriochlorin-13¹-(2-sulfethyl)amide-17³-(2-trimethylaminoethyl)ester
• 英文别名: 2-[3-[(2S,3S,12R,13R)-8-acetyl-13-ethyl-20-(2-methoxy-2-oxoethyl)-3,7,12,17-tetramethyl-18-(2-sulfoethylcarbamoyl)-2,3,12,13,22,24-hexahydroporphyrin-2-yl]propanoyloxy]ethyl-trimethylazanium
• 化学式: C₄₂H₅₇N₆O₉S
• 分子量: 822.015
• InChiKey: WNLGPWWOZBMXIK-LXEIEBNOSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  58.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  210.5
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  bacteriopheophytin a 在 4-二甲氨基吡啶 、 dipotassium hydrogenphosphate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 260.0h， 生成 3¹-oxo-15-methoxycarbonylmethyl-rhodobacteriochlorin-13¹-(2-sulfethyl)amide-17³-(2-trimethylaminoethyl)ester
  参考文献：
  名称：

  Modulation of Reactive Oxygen Species Photogeneration of Bacteriopheophorbide a Derivatives by Exocyclic E-Ring Opening and Charge Modifications

  摘要：

  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.

  DOI：

  10.1021/jm401538h

文献信息

• 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.