6-[2-[2-[2-chloro-3-[2-[1-(2-hydroxyethyl)quinolin-1-ium-4-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-1,1-dimethylbenzo[e]indol-3-yl]hexanoic acid;iodide | 1360817-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-[2-[2-[2-chloro-3-[2-[1-(2-hydroxyethyl)quinolin-1-ium-4-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-1,1-dimethylbenzo[e]indol-3-yl]hexanoic acid;iodide
• CAS: 1360817-78-2
• 化学式: C₄₁H₄₄ClN₂O₃*I
• 分子量: 775.169
• InChiKey: VKNKQAONDDHFHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  64.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 6-[2-[2-[2-chloro-3-[2-[1-(2-hydroxyethyl)quinolin-1-ium-4-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-1,1-dimethylbenzo[e]indol-3-yl]hexanoic acid;iodide 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 以15.6%的产率得到
  参考文献：
  名称：

  Development of Novel Nanocarrier-Based Near-Infrared Optical Probes for In Vivo Tumor Imaging

  摘要：

  近红外（NIR）荧光探针的光学成像是一种用于体内肿瘤检测的有用诊断技术。我们的计划是开发新型近红外荧光团-胶束复合探针。我们合成了 IC7-1 和 IC7-2，作为新型亲脂性近红外荧光团，并将其封装在两亲性聚表肽胶束 "乳糖体 "中。荧光团-胶束复合物 IC7-1 乳糖体和 IC7-2 乳糖体被评估为用于体内肿瘤成像的近红外荧光探针。IC7-1 和 IC7-2 经合成后封装在乳糖体中。测量了 IC7-1、IC7-2、IC7-1 乳糖体和 IC7-2 乳糖体的光学特性。给肿瘤小鼠注射IC7-1乳糖体和IC7-2乳糖体，48 h后采集荧光图像。IC7-1和IC7-2成功合成，总产率分别为12%和6.3%，在氯仿中的最大发射波长分别为858 nm和897 nm。与 ICG 相比，IC7-1 乳糖体和 IC7-2 乳糖体的缓冲水溶液在氯仿中显示出相似的荧光光谱、更高或相当的量子产率和更高的光稳定性。两种乳糖体探针都能在给药后 6 h 特异性地观察到肿瘤组织。IC7-1乳糖体和IC7-2乳糖体有望成为体内肿瘤成像的近红外探针。

  DOI：

  10.1007/s10895-011-1007-z
• 作为产物：
  描述：

  6-溴己酸 在 sodium acetate 、 potassium iodide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 29.0h， 生成 6-[2-[2-[2-chloro-3-[2-[1-(2-hydroxyethyl)quinolin-1-ium-4-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-1,1-dimethylbenzo[e]indol-3-yl]hexanoic acid;iodide
  参考文献：
  名称：

  Development of Novel Nanocarrier-Based Near-Infrared Optical Probes for In Vivo Tumor Imaging

  摘要：

  近红外（NIR）荧光探针的光学成像是一种用于体内肿瘤检测的有用诊断技术。我们的计划是开发新型近红外荧光团-胶束复合探针。我们合成了 IC7-1 和 IC7-2，作为新型亲脂性近红外荧光团，并将其封装在两亲性聚表肽胶束 "乳糖体 "中。荧光团-胶束复合物 IC7-1 乳糖体和 IC7-2 乳糖体被评估为用于体内肿瘤成像的近红外荧光探针。IC7-1 和 IC7-2 经合成后封装在乳糖体中。测量了 IC7-1、IC7-2、IC7-1 乳糖体和 IC7-2 乳糖体的光学特性。给肿瘤小鼠注射IC7-1乳糖体和IC7-2乳糖体，48 h后采集荧光图像。IC7-1和IC7-2成功合成，总产率分别为12%和6.3%，在氯仿中的最大发射波长分别为858 nm和897 nm。与 ICG 相比，IC7-1 乳糖体和 IC7-2 乳糖体的缓冲水溶液在氯仿中显示出相似的荧光光谱、更高或相当的量子产率和更高的光稳定性。两种乳糖体探针都能在给药后 6 h 特异性地观察到肿瘤组织。IC7-1乳糖体和IC7-2乳糖体有望成为体内肿瘤成像的近红外探针。

  DOI：

  10.1007/s10895-011-1007-z

文献信息

• SWITCHING FLUORESCENT NANOPARTICLE PROBE AND FLUORESCENT PARTICLE IMAGING METHOD USING SAME
  申请人：Hara Isao

  公开号：US20130149252A1

  公开（公告）日：2013-06-13

  The present invention provides a novel fluorescent nanoparticle imaging probe having a switching function (a function to quench a fluorescent dye during nanoparticle preparation, and emit fluorescence during imaging). A switching fluorescent nanoparticle probe comprising: a molecular assembly composed of an amphiphilic block polymer having a hydrophilic block chain and a hydrophobic block chain; and a fluorescent dye encapsulated in the molecular assembly, wherein (a) the hydrophilic block chain comprises, as an essential hydrophilic structural unit, a unit selected from a sarcosine unit and an alkylene oxide unit, (b) the hydrophobic block chain comprises, as an essential hydrophobic structural unit, a unit selected from the group consisting of an amino acid unit and a hydroxylic acid unit, and (c) the fluorescent dye is a cyanine compound represented by the formula (I): and two or more molecules of the fluorescent dye are encapsulated in the single molecular assembly.

  本发明提供一种新型荧光纳米颗粒成像探针，具有切换功能（在纳米颗粒制备过程中熄灭荧光染料，并在成像过程中发射荧光）。一种切换荧光纳米颗粒探针包括：由具有亲水性块链和疏水性块链的两性块聚合物组成的分子组装体；以及封装在分子组装体中的荧光染料，其中（a）亲水性块链包括作为必要亲水性结构单元的一种选自肌氨酸单元和烷氧基单元的单元，（b）疏水性块链包括作为必要疏水性结构单元的一种选自氨基酸单元和羟基酸单元的单元，（c）荧光染料是由式（I）表示的青菁化合物：并且两个或更多分子的荧光染料被封装在单个分子组装体中。
• Switching fluorescent nanoparticle probe and fluorescent particle imaging method using same
  申请人：Hara Isao

  公开号：US09370589B2

  公开（公告）日：2016-06-21

  The present invention provides a novel fluorescent nanoparticle imaging probe having a switching function (a function to quench a fluorescent dye during nanoparticle preparation, and emit fluorescence during imaging). A switching fluorescent nanoparticle probe comprising: a molecular assembly composed of an amphiphilic block polymer having a hydrophilic block chain and a hydrophobic block chain; and a fluorescent dye encapsulated in the molecular assembly, wherein (a) the hydrophilic block chain comprises, as an essential hydrophilic structural unit, a unit selected from a sarcosine unit and an alkylene oxide unit, (b) the hydrophobic block chain comprises, as an essential hydrophobic structural unit, a unit selected from the group consisting of an amino acid unit and a hydroxylic acid unit, and (c) the fluorescent dye is a cyanine compound represented by the formula (I): and two or more molecules of the fluorescent dye are encapsulated in the single molecular assembly.

  本发明提供了一种具有开关功能的新型荧光纳米颗粒成像探针（在纳米颗粒制备过程中熄灭荧光染料并在成像过程中发射荧光）。一种开关式荧光纳米颗粒探针包括：由具有亲水性块链和疏水性块链的两性块聚合物组成的分子组装体；以及封装在分子组装体中的荧光染料，其中（a）亲水性块链包括作为基本亲水性结构单元的从一种肌氨酸单元和一种烷氧基烷单元中选择的单元，（b）疏水性块链包括作为基本疏水性结构单元的从一种氨基酸单元和一种羟基酸单元中选择的单元，以及（c）荧光染料是由式（I）表示的青铵化合物，且两个或更多分子的荧光染料封装在单个分子组装体中。
• Development of Novel Nanocarrier-Based Near-Infrared Optical Probes for In Vivo Tumor Imaging
  作者：Yoichi Shimizu、Takashi Temma、Isao Hara、Ryo Yamahara、Ei-ichi Ozeki、Masahiro Ono、Hideo Saji

  DOI：10.1007/s10895-011-1007-z

  日期：2012.3

  Optical imaging with near-infrared (NIR) fluorescent probes is a useful diagnostic technology for in vivo tumor detection. Our plan was to develop novel NIR fluorophore-micelle complex probes. IC7-1 and IC7-2 were synthesized as novel lipophilic NIR fluorophores, which were encapsulated in an amphiphilic polydepsipeptide micelle “lactosome”. The fluorophore-micelle complexes IC7-1 lactosome and IC7-2 lactosome were evaluated as NIR fluorescent probes for in vivo tumor imaging. IC7-1 and IC7-2 were synthesized and then encapsulated in lactosomes. The optical properties of IC7-1, IC7-2, IC7-1 lactosome and IC7-2 lactosome were measured. IC7-1 lactosome and IC7-2 lactosome were administered to tumor-bearing mice, and fluorescence images were acquired for 48 h. IC7-1 and IC7-2 were successfully synthesized in 12% and 6.3% overall yield, and maximum emission wavelengths in chloroform were observed at 858 nm and 897 nm, respectively. Aqueous buffered solutions of IC7-1 lactosome and IC7-2 lactosome showed similar fluorescence spectra in chloroform and higher or comparable quantum yields and higher photostability compared with ICG. Both lactosome probes specifically visualized tumor tissue 6 h post-administration. IC7-1 lactosome and IC7-2 lactosome could be promising NIR probes for in vivo tumor imaging.

  近红外（NIR）荧光探针的光学成像是一种用于体内肿瘤检测的有用诊断技术。我们的计划是开发新型近红外荧光团-胶束复合探针。我们合成了 IC7-1 和 IC7-2，作为新型亲脂性近红外荧光团，并将其封装在两亲性聚表肽胶束 "乳糖体 "中。荧光团-胶束复合物 IC7-1 乳糖体和 IC7-2 乳糖体被评估为用于体内肿瘤成像的近红外荧光探针。IC7-1 和 IC7-2 经合成后封装在乳糖体中。测量了 IC7-1、IC7-2、IC7-1 乳糖体和 IC7-2 乳糖体的光学特性。给肿瘤小鼠注射IC7-1乳糖体和IC7-2乳糖体，48 h后采集荧光图像。IC7-1和IC7-2成功合成，总产率分别为12%和6.3%，在氯仿中的最大发射波长分别为858 nm和897 nm。与 ICG 相比，IC7-1 乳糖体和 IC7-2 乳糖体的缓冲水溶液在氯仿中显示出相似的荧光光谱、更高或相当的量子产率和更高的光稳定性。两种乳糖体探针都能在给药后 6 h 特异性地观察到肿瘤组织。IC7-1乳糖体和IC7-2乳糖体有望成为体内肿瘤成像的近红外探针。