4-(1,1-Dimethyl-2-oxobenzo[e]indol-3-yl)butane-1-sulfonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(1,1-Dimethyl-2-oxobenzo[e]indol-3-yl)butane-1-sulfonate
• 化学式: C₁₈H₂₀NO₄S
• 分子量: 346.427
• InChiKey: AORLHYGMJYDEHR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  以 水 为溶剂， 生成 4-(1,1-Dimethyl-2-oxobenzo[e]indol-3-yl)butane-1-sulfonate 、
  参考文献：
  名称：

  Effect of Metalation on Porphyrin-Based Bifunctional Agents in Tumor Imaging and Photodynamic Therapy

  摘要：

  在此，我们报告了 3-(1'-己氧基)乙基-3-脱乙烯基焦脱镁叶绿酸-花青染料 (HPPH-CD) 和相应的铟 (In)、镓的合成和比较光物理、电化学、体外和体内生物学功效。 (Ga) 和钯 (Pd) 缀合物。 HPPH 部分中插入重金属会导致 FRET（福斯特共振能量转移）和电化学特性产生显着差异，这与单线态氧的产生（光动力疗法 (PDT) 的关键细胞毒剂）和体内长期作用相关PDT疗效。在金属化类似物中，In(III) HPPH-CD 显示出最佳的癌症成像和 PDT 功效。有趣的是，与游离碱 HPPH-CD 需要的治疗剂量 (2.5 μmol/kg) 显着高于成像剂量 (0.3 μmol/kg) 相比，相应的 In(III) HPPH-CD 在在携带 Colon26 肿瘤的 BALB/c 小鼠中，剂量非常低（0.3 μmol/kg）。金属化和相应的非金属化缀合物的比较研究进一步证实STAT-3二聚化可以作为确定光反应和肿瘤反应水平的生物标志物。

  DOI：

  10.1021/acs.bioconjchem.5b00656

文献信息

• Impact of Substituents in Tumor Uptake and Fluorescence Imaging Ability of Near-Infrared Cyanine-like Dyes
  作者：Nayan J. Patel、Ethirajan Manivannan、Penny Joshi、Tymish J. Ohulchanskyy、Roger R. Nani、Martin J. Schnermann、Ravindra K. Pandey

  DOI：10.1111/php.12482

  日期：2015.9

  AbstractThis report presents a simple strategy to introduce various functionalities in a cyanine dye (bis‐indole‐N‐butylsulfonate‐polymethine bearing a fused cyclic chloro‐cyclohexene ring structure), and assess the impact of these substitutions in tumor uptake, retention and imaging. The results obtained from the structural activity relationship (SAR) study demonstrate that certain structural features introduced in the cyanine dye moiety make a remarkable difference in tumor avidity. Among the compounds investigated, the symmetrical CDs containing an amino‐phenyl thioether group attached to a cyclohexene ring system and the two N‐butyl linkers with terminal sulfonate groups in benzoindole moieties exhibited excellent tumor imaging ability in BALB/c mice bearing Colon26 tumors. Compared to indocyanine green (ICG), approved by FDA as a blood pooling agent, which has also been investigated for the use in tumor imaging, the modified CD selected on the basis of SAR study produced enhanced uptake and longer retention in tumor(s). A facile approach reported herein for introducing a variety of functionalities in tumor‐avid CD provides an opportunity to create multi‐imaging modality agent(s). Using a combination of mass spectrometry and absorbance techniques, the photobleaching of one of the CDs was analyzed and significant regioselective photooxidation was observed.