2,3,4,5-Tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)-benzoic acid 5-carboxy-pentyl ester | 106805-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,3,4,5-Tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)-benzoic acid 5-carboxy-pentyl ester
• 英文别名: 6-[2,3,4,5-Tetrachloro-6-(3-hydroxy-2,4,5,7-tetraiodo-6-oxoxanthen-9-yl)benzoyl]oxyhexanoic acid
• CAS: 106805-54-3
• 化学式: C₂₆H₁₄Cl₄I₄O₇
• 分子量: 1087.82
• InChiKey: OVJRBVQOQLDAHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,4,5-Tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)-benzoic acid 5-carboxy-pentyl ester 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Photosensitizer-Antibiotic Conjugates: A Novel Class of Antibacterial Molecules

  摘要：

  AbstractBacterial resistance to a variety of antibiotics has led to intensive research into the effect of photosensitizers as a cytotoxic agent against bacterial cells. In this study, we synthesized the following conjugates with or without a linker: rose bengal‐penicillanic acid (RBPA), rose bengal‐linker‐penicillanic acid (RBLPA) and rose bengal‐linker‐kanamycin (RBLKAN). The antibacterial activity of these conjugates was examined on Staphylococcus aureus and Escherichia coli. Exposure of the cultures to 100 J cm−2 showed that the minimum inhibitory concentration (MIC) of RBPA, RBLPA and RBLKAN on S. aureus was 0.195, 0.156 and 0.004 μm, respectively. The MIC of RBPA, RBLPA and RBLKAN on E. coli was 1.56, 2.5 and 0.156 μm, respectively. In dark control experiments, the MIC of these conjugates was not detected until a concentration that was 16‐fold that of the MIC found in the light experiments. RBPA and RBLPA as well as RBLKAN are bactericidal for both bacterial cells. Total eradication of S. aureus and E. coli was observed with RBLKAN (0.078 and 20 μm 16 J cm−2, respectively). Under these conditions, scanning electron microscopic analysis showed significant damage to these bacteria. However, the photosensitizer and antibiotics individually were not effective.

  DOI：

  10.1111/j.1751-1097.2009.00674.x
• 作为产物：
  描述：

  6-溴己酸 、 rose bengal 以 水 、 丙酮 为溶剂， 反应 24.0h， 以22%的产率得到2,3,4,5-Tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)-benzoic acid 5-carboxy-pentyl ester
  参考文献：
  名称：

  Synthesis, Characterization, and Cellular Uptake of DNA-Binding Rose Bengal Peptidoconjugates

  摘要：

  Peptide conjugates of the xanthene dye rose bengal (RB) are described featuring sequences that promote DNA binding. The complexation of these conjugates with DNA causes efficient quenching of the fluorophore singlet state and suppresses singlet oxygen production. When incubated with human cells, the RB conjugates pass through the cell membrane but are not visualized in the nucleus. This behavior is in stark contrast to that exhibited by structurally analogous conjugates containing the unhalogenated xanthene dye fluorescein. These results highlight the marked sensitivity of cell permeability characteristics to subtle structural differences.

  DOI：

  10.1021/ol047762+

文献信息

• [EN] PHOTOTOXIC COMPOUNDS<br/>[FR] COMPOSES PHOTOTOXIQUES
  申请人：TRUSTEES BOSTON COLLEGE

  公开号：WO2005123105A1

  公开（公告）日：2005-12-29

  The invention discloses various phototoxic compounds which include a photosensitizer conjugated to a peptide or peptoid. Additionally, the invention discloses a method of making and using the various phototoxic compound. Furthermore, the invention discloses using such phototoxic compound for DNA cleavage and for causing cytotoxic effect in a biological system. Additionally, the present invention features using the phototoxic compound for treating diseases in a subject.

  本发明公开了多种光毒性化合物，其中包括与肽或peptoid共轭的光敏剂。此外，本发明还公开了一种制备和使用各种光毒性化合物的方法。此外，本发明还公开了使用这种光毒性化合物进行DNA断裂和在生物系统中引起细胞毒性效应的方法。此外，本发明还特别涉及使用这种光毒性化合物治疗主体中的疾病。
• An orthogonally activatable CRISPR-Cas13d nanoprodrug to reverse chemoresistance for enhanced chemo-photodynamic therapy
  作者：Zheng Liu、Zhiyuan Feng、Mohan Chen、Jiayin Zhan、Rong Wu、Yang Shi、Yunsheng Xue、Ran Liu、Jun-Jie Zhu、Jingjing Zhang

  DOI：10.1039/d3sc00020f

  日期：——

  orthogonal emissive upconversion nanoparticles (UCNPs), we herein rationally designed the first logic-gated CRISPR-Cas13d-based nanoprodrug for orthogonal photomodulation of gene editing and prodrug release for enhanced cancer therapy. The nanoprodrug (URL) was constructed by encapsulating a green light-activatable Pt(IV) prodrug and UV light-activatable Cas13d gene editing tool into UCNPs. We demonstrated

  结合基于 CRISPR 的基因编辑和基于前体药物的化学疗法的正交疗法是对抗多药耐药癌症的一种很有前途的方法。然而，由于缺乏具有高时空分辨率的集成平台，其在体内精确调节不同治疗方式的能力受到限制。利用 CRISPR 技术，一种基于 Pt( IV ) 的前药和正交发射上转换纳米颗粒 (UCNP)，我们在此合理设计了第一个基于逻辑门控 CRISPR-Cas13d 的纳米前药，用于基因编辑的正交光调制和增强癌症的前药释放治疗。纳米前药 (URL) 是通过封装绿光可激活的 Pt( IV) 前药和 UV 光可激活的 Cas13d 基因编辑工具进入 UCNPs。我们证明了 URL 在 808 和 980 nm 激发下保持出色的正交发射行为，允许 Cas13d 的波长选择性光激活和前药分别用于下调耐药相关基因和诱导化学光动力疗法。此外，通过将 URL 与用于对多细胞行为进行可编程调制的布尔逻辑门集成，突出了
• [EN] DYE IMAGING AGENTS<br/>[FR] AGENTS D'IMAGERIE À BASE DE COLORANT
  申请人：GE HEALTHCARE LTD

  公开号：WO2008003954A1

  公开（公告）日：2008-01-10

  [EN] The present invention relates to diagnostic imaging agents forin vivo imaging. The imaging agents are radiopharmaceuticals and comprise a class of xanthene dye labelled with a radiohalogen isotope or with a non-metallic positron-emitting radioisotope suitable for diagnostic imaging in vivo.
  [FR] La présente invention concerne des agents d'imagerie diagnostique destinés à l'imagerie in vivo. Les agents d'imagerie sont des produits radiopharmaceutiques et contiennent une classe de colorant de type xanthène marqué avec un radio-isotope halogène ou avec un radio-isotope émettant des positrons non métallique, approprié pour l'imagerie diagnostique in vivo.