4-Ethoxy-3-trimethylstannanyl-benzaldehyde | 184033-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Ethoxy-3-trimethylstannanyl-benzaldehyde
• 英文别名: Benzaldehyde, 4-ethoxy-3-(trimethylstannyl)-；4-ethoxy-3-trimethylstannylbenzaldehyde
• CAS: 184033-47-4
• 化学式: C₁₂H₁₈O₂Sn
• 分子量: 312.984
• InChiKey: IDSZDZAKPVRIPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Ethoxy-3-trimethylstannanyl-benzaldehyde 、 2-(3,4-diaminophenyl)-6-(1-methyl-4-piperazinyl)benzimidazole 在 sodium hydroxide 、 molecular sieve 、 sodium iodide 、 acetate buffer 、 双氧水 、 lactoperoxidase 作用下， 生成 2-[2-(3-[125I]iodo-4-ethoxyphenyl)-6-benzimidazolyl]-6-(1-methyl-4-piperazinyl)benzimidazole
  参考文献：
  名称：

  [¹²⁵I/¹²⁷I]IodoHoechst 33342:  Synthesis, DNA Binding, and Biodistribution

  摘要：

  An iodinated analog of the DNA-minor-groove-binding agent Hoechst 33342 has been synthesized and evaluated for DNA binding and tumor targeting. The bis-benzimidazole ring system of the title compound was constructed from the piperazinyl terminus via a Pinner-type cyclization followed by oxidative cyclization of the diamine Schiff base. To synthesize radioiodoHoechst 33342, (trimethylstannyl)Hoechst 33342 was prepared by the same strategy and subjected to mild radioiodedestannylation in the presence of lactoperoxidase. After purification by HPLC, the radiochemical was separated in carrier-free form with >85% radiochemical yield and >99% chemical and radiochemical purity. Fluorescence spectrometric analysis of the binding of iodoHoechst 33342 calf thymus DNA gave an equilibrium association constant (K-a) of 2.57 x 10(7) M(-1) comparable to the K-a value of Hoechst 33342. Fluorescence microscopy of viable V79 cells demonstrated that the iodinated dye stained the nuclei with avidity similar to that of the noniodinated dye. The biodistribution of [I-125]-iodoHoechst 33342 in LS174T tumor-bearing athymic mice 4 h postadministration showed a tumor uptake of 3-4% injected dose per gram (ID/g), tumor/blood ratio of 6-8, and tumor/nontumor ratios above unity for most organs. A low thyroid uptake (similar to 2% ID/g) indicated that the radiochemical did not deiodinate and was stable in vivo.

  DOI：

  10.1021/jm9602672

文献信息

• [¹²⁵I/¹²⁷I]IodoHoechst 33342:  Synthesis, DNA Binding, and Biodistribution
  作者：Ravi S. Harapanhalli、Larry W. McLaughlin、Roger W. Howell、Dandamudi V. Rao、S. James Adelstein、Amin I. Kassis

  DOI：10.1021/jm9602672

  日期：1996.1.1

  An iodinated analog of the DNA-minor-groove-binding agent Hoechst 33342 has been synthesized and evaluated for DNA binding and tumor targeting. The bis-benzimidazole ring system of the title compound was constructed from the piperazinyl terminus via a Pinner-type cyclization followed by oxidative cyclization of the diamine Schiff base. To synthesize radioiodoHoechst 33342, (trimethylstannyl)Hoechst 33342 was prepared by the same strategy and subjected to mild radioiodedestannylation in the presence of lactoperoxidase. After purification by HPLC, the radiochemical was separated in carrier-free form with >85% radiochemical yield and >99% chemical and radiochemical purity. Fluorescence spectrometric analysis of the binding of iodoHoechst 33342 calf thymus DNA gave an equilibrium association constant (K-a) of 2.57 x 10(7) M(-1) comparable to the K-a value of Hoechst 33342. Fluorescence microscopy of viable V79 cells demonstrated that the iodinated dye stained the nuclei with avidity similar to that of the noniodinated dye. The biodistribution of [I-125]-iodoHoechst 33342 in LS174T tumor-bearing athymic mice 4 h postadministration showed a tumor uptake of 3-4% injected dose per gram (ID/g), tumor/blood ratio of 6-8, and tumor/nontumor ratios above unity for most organs. A low thyroid uptake (similar to 2% ID/g) indicated that the radiochemical did not deiodinate and was stable in vivo.