2-[(1E,3Z)-3-氯-5-(1,3,3-三甲基-1,3-二氢-2H-吲哚-2-亚基)-1,3-戊二烯基]-1,3,3-三甲基-3H-吲哚碘化物 | 119569-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2-[(1E,3Z)-3-氯-5-(1,3,3-三甲基-1,3-二氢-2H-吲哚-2-亚基)-1,3-戊二烯基]-1,3,3-三甲基-3H-吲哚碘化物
• 英文名称: MHI-106
• 英文别名: 3-chloro-1,5-bis-(1,3,3-trimethyl-3H-indol-2-yl)-pentamethinium ; iodide；3-Chlor-1,5-bis-(1,3,3-trimethyl-3H-indol-2-yl)-pentamethinium; Jodid；2-[(2Z,4E)-3-chloro-5-(1,3,3-trimethylindol-1-ium-2-yl)penta-2,4-dienylidene]-1,3,3-trimethylindole;iodide
• CAS: 119569-97-0
• 化学式: C₂₇H₃₀ClN₂*I
• 分子量: 544.906
• InChiKey: LALXFJVJPCWWQU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯胺 在 sodium acetate 、 乙酸酐 作用下， 以 乙醇 为溶剂， 生成 2-[(1E,3Z)-3-氯-5-(1,3,3-三甲基-1,3-二氢-2H-吲哚-2-亚基)-1,3-戊二烯基]-1,3,3-三甲基-3H-吲哚碘化物
  参考文献：
  名称：

  Correlating Molecular Character of NIR Imaging Agents with Tissue-Specific Uptake

  摘要：

  Near-infrared (NIR) fluorescent contrast agents are emerging in optical imaging as sensitive, cost-effective, and nonharmful alternatives to current agents that emit harmful ionizing radiation. Developing spectrally distinct NIR fluorophores to visualize sensitive vital tissues to selectively avoid them during surgical resection of diseased tissue is of great significance. Herein, we report the synthetic variation of pentamethine cyanine fluorophores with modifications of physicochemical, properties toward prompting tissue-specific uptake into sensitive tissues (i.e., endocrine glands). Tissue-specific targeting and biodistribution studies revealed localization of contrast agents in the adrenal and pituitary glands, pancreas, and lymph nodes with dependence on molecular characteristics. Incorporation of hydrophobic heterocyclic rings, alkyl groups, and halogens allowed a fine tuning capability to the hydrophobic character and dipole moment for observing perturbation in biological activity in response to minor structural alterations. These NIR contrast agents have potential for clinical translation for intraoperative imaging in the,delineation of delicate glands.

  DOI：

  10.1021/acs.jmedchem.5b00475

文献信息

• 신호대 배경비 향상을 위한 전하 균형 형광 조영제 및 이를 이용한 영상화 방법
  申请人：Pusan National University Industry-University Cooperation Foundation 부산대학교 산학협력단(220040044843) BRN ▼621-82-06530

  公开号：KR20180131102A

  公开（公告）日：2018-12-10

  본 발명은 영상 유도 수술용 형광 영상 장치를 사용하여 조직 및 세포를 광학적으로 관찰할 때 높은 신호 대 배경 비를 낼 수 있도록 한 전하 균형 형광 조영제에 관한 것으로, 조직 또는 세포를 영상화하기 위한 조영제를 포함하며, 상기 조영제는 신호 대 배경 비가 적어도 1.1 이상으로 검출되도록 형광을 방출하는 것을 특징으로 하는 결합체를 포함하며, 상기 접합체는 화학식 I: 으로 표시되는 것이다.

  本发明涉及使用荧光成像设备进行显微手术时，关于电荷平衡荧光造影剂，以便在光学上观察组织和细胞时获得高信号对噪声比的技术。该造影剂包括用于成像组织或细胞的造影剂，其中该造影剂包括至少发射荧光以使信号对噪声比检测到至少1.1的复合物，该复合物以化学式I表示。
• Beattie et al., Journal of the Chemical Society, 1932, p. 260,265
  作者：Beattie et al.

  DOI：——

  日期：——
• Correlating Molecular Character of NIR Imaging Agents with Tissue-Specific Uptake
  作者：Eric A. Owens、Hoon Hyun、Joseph G. Tawney、Hak Soo Choi、Maged Henary

  DOI：10.1021/acs.jmedchem.5b00475

  日期：2015.5.28

  Near-infrared (NIR) fluorescent contrast agents are emerging in optical imaging as sensitive, cost-effective, and nonharmful alternatives to current agents that emit harmful ionizing radiation. Developing spectrally distinct NIR fluorophores to visualize sensitive vital tissues to selectively avoid them during surgical resection of diseased tissue is of great significance. Herein, we report the synthetic variation of pentamethine cyanine fluorophores with modifications of physicochemical, properties toward prompting tissue-specific uptake into sensitive tissues (i.e., endocrine glands). Tissue-specific targeting and biodistribution studies revealed localization of contrast agents in the adrenal and pituitary glands, pancreas, and lymph nodes with dependence on molecular characteristics. Incorporation of hydrophobic heterocyclic rings, alkyl groups, and halogens allowed a fine tuning capability to the hydrophobic character and dipole moment for observing perturbation in biological activity in response to minor structural alterations. These NIR contrast agents have potential for clinical translation for intraoperative imaging in the,delineation of delicate glands.
• Near-Infrared Illumination of Native Tissues for Image-Guided Surgery
  作者：Eric A. Owens、Hoon Hyun、Tyler L. Dost、Jeong Heon Lee、GwangLi Park、Dang Huan Pham、Min Ho Park、Hak Soo Choi、Maged Henary

  DOI：10.1021/acs.jmedchem.6b00038

  日期：2016.6.9

  Our initial efforts to prepare tissue-specific near infrared (NIR) fluorescent compounds generated successful correlation between physicochemical, properties and global uptake in major organs after systemic circulation and biodistribution. Herein, we focus on the effects on biodistribution based on modulating electronic influencing moieties from donating to withdrawing moieties at both the heterocyclic site and through meso-substitution of pentamethine cyanine fluorophores. These selected modifications harnessed innate biodistribution pathways through the structure-inherent targeting, resulting in effective imaging of the adrenal glands, pituitary gland, lymph nodes, pancreas, and thyroid and salivary glands. These native-tissue contrast agents will arm surgeons with a powerful and versatile arsenal for intraoperative NIR imaging in real time.